Before I dig into the concrete things you can learn and do, I want to say that it is okay to feel anxious. We have all felt like imposters in roles we were actually extremely qualified to perform. After twenty-plus years in this industry, I still sometimes feel like I have no idea what I am doing. It is completely okay to feel a heightened sense of insecurity when you have to lead a team whose core function is not your core competency. However, keep this in mind. You are an experienced leader, and ninety percent of patterns repeat across departments and functions. Think of leading a different department not as learning a new language, but as learning a new dialect.

That is the good news. The reality check is this: to lead another department or team of individual contributors whose job you have never done, you do need real management experience behind you. Put it another way, the answer to “Have you delivered value through others?” should be yes. You cannot go from being a software engineer to managing a team of product managers without first having managed people. I would say you need at least five years of successfully leading a team before you attempt to lead one whose job you cannot do yourself. Learning a new dialect requires that you already speak the language. With that, let’s get into it.

1. Learn

The most reliable way to build fluency in an unfamiliar domain is through books. Specifically, books written by practitioners who have actually done the job and not the pundits and gurus.

I read fifty-plus books a year across fiction, non-fiction, and everything in between. I would not be overstating it to say that habit has given me a meaningful advantage when it comes to promotions and new opportunities. If you have not read seriously in a while, start now. If non-fiction feels dry, start with fiction and cross over. The medium matters less than the habit.

Once you have the theory, observe. Watch how the functional leaders in your current company run their departments, set goals, and make decisions. If you have a good relationship with a leader whose domain you want to understand, ask to shadow them. Sit in on their meetings. Most good leaders will say yes if you just ask. Come with no agenda other than to understand how they think.

Building this level of fluency, if you do the work seriously, takes a seasoned leader roughly five years. By the end of it, you should be able to answer three questions about the team at a high level: What does the day-to-day of an individual contributor on this team actually look like? What goals do they track at a departmental level? How do the leaders decide what those goals should be?

One thing I want to call out explicitly before moving on. You will only get what you put in. If you half-ass the learning, everything that follows will fall apart and may cause lasting reputation damage. Putting in the work is the easiest thing to get right, and yet most people fail at it. The more work you put in, the higher your chances of success. It is that simple.

2. Trust

One of my favorite sci-fi shows, after Battlestar Galactica, is Stargate Atlantis. For those who have not seen it, the show follows a cross-disciplinary team of scientists and soldiers exploring a new galaxy. The leader of the expedition is a scientist, Dr. Weir, and the show captures exactly the tension you will experience when you take over a team whose job you cannot do. She is technically the leader of the entire crew, but in the early episodes, the soldiers actively disregard her directions. Over time, Dr. Weir earns their respect and eventually convinces the military contingent to see her as their commander. The tactics she uses are very similar to what I have used in my own career.

The first thing she does is trust the people to do their jobs. She includes the military leaders in her decision-making and does not undermine their calls. That does not mean she blindly accepts their recommendations. She respectfully pushes back when their point of view conflicts with the core objectives of the mission. She is clear about her goals and makes the appropriate decisions while taking everyone’s input into account.

Obviously, Dr. Weir is fictional, but her approach to building trust with a team that does not fully trust her yet is extremely applicable to tech leadership. When you take over a new team, trust is the first job. Spend time with them. This is so simple and so consistently underdone that it still surprises me. Trust the people on your team to do the job and manage toward outcomes, not implementation details. Actively remove blockers from their path. And disagree with them when their point of view pushes you further from your goals. There is potentially an entire book waiting to be written about this topic, but the bottom line is this: know your goals, understand how they tie into the company’s future, trust your team to do the work, and help them become successful.

3. Know what success looks like

Since we are on a sci-fi kick, let’s keep it going. This time, I am going to use an example from my all-time favorite sci-fi show: Battlestar Galactica (BSG). For the uninitiated, BSG is the story of a ragtag group of humans who have to flee their home to survive an attack by an alien civilization. The leader of that group is the recently promoted President Laura Roslin, now responsible for keeping the entire human race alive. The scene that has stayed with me is when President Roslin wheels a whiteboard into her makeshift office and writes a single number on it. Population. The number of living humans. That is her metric. It is her only metric.

BSG is fictional, but having a clear point of view on what success looks like is not just good television writing. It is your job. Understand what success looks like for your team, define the metrics, and align everyone around them. Pressure test those metrics constantly to make sure they are not vanity metrics. That means having a regular process to monitor and discuss them and getting honest feedback from stakeholders. Also, remember that metrics come in two flavors: input metrics, which your team can directly influence, and output metrics, which are company-level results like revenue and churn. Your team should be moving input metrics. The output metrics will follow. There is an entire discipline around this, but the meta point is simple: know what winning looks like, write it on the whiteboard, and make sure everyone can see it.

4. Build the right process

You have built trust with your team, and you know what your goals are. How do you ensure things are moving in the right direction? There are multiple tactical things you can deploy, like business reviews, agile, scrum, and so on, but at its core, the question you should be asking yourself as a leader is:

“Are the right people working on the right projects at the right pace?”

That is it. However, you end up designing your processes, they should help you answer that question.

Right people means you have the talent the team actually needs, not just the talent the team has always had. You may not be able to evaluate the craft directly, but you can observe the signals around it. Are the people on this team trusted by their peers? Are they making decisions that hold up over time? Are the leaders around them leaning on them or working around them? You do not need to know how to do the job to answer those questions. You just need to pay attention.

Right projects means the work your team is doing today is connected to the metrics you defined in the previous section. This is where the “So What?” question earns its place. Before any major initiative gets your sign-off, ask it. Why does this work matter? What happens if we do not do it? How does it move the metrics that actually matter to the business? A lot of teams are busy on work that made sense six months ago and has not been pressure tested since. Your job is to pressure test it.

Right pace means decisions are moving, not stacking up. The highest-leverage thing you can do for a team whose work you cannot evaluate directly is unblock their decision-making. Most new leaders in an unfamiliar domain hold decisions too long because they lack confidence in their domain knowledge. That hesitation costs the team more than a wrong call would. Learn to distinguish one-way doors from two-way doors. Most decisions are two-way. Let the team make them. Reserve your intervention for the ones that are genuinely hard to walk back.

If you can answer yes to all three, the team is healthy. If one of them is off, you now know exactly where to focus.

5. Give it time

None of this happens in the first month. Probably not in the first quarter either.

The leaders who struggle most in this transition are the ones who expect the team to trust them before they have earned it, who expect to understand the work before they have observed it, and who expect to see results before they have built the conditions for results to happen. That impatience is understandable. It is also expensive.

The arc looks something like this. In the first ninety days, you are learning and listening. You are spending time with the team, understanding the work, and building the relationships that will carry everything else. In the next ninety days, you are starting to form a point of view. You know what success looks like. You are pressure testing the metrics and the projects. You are starting to spot what is working and what is not. By the end of the first year, if you have done the work, you are leading.

Twenty-plus years in this industry have taught me one thing about leading people whose job you cannot do: the craft you lack matters far less than the judgment you bring. Trust the team. Know what winning looks like. Build the conditions for them to get there. And give it the time it actually takes.

PS: I have a lot more to say on this topic, so I have been quietly building something for senior leaders who want to make this transition the right way. It is almost ready. Watch this space.

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The biggest reason I am comfortable making this prediction is that the future is already here, to some extent. Companies are increasingly combining multiple functional leadership and executive roles into one unified role. CPTO (product+engineering executive) searches have surged 110%. Cost is one minor aspect of the reasoning, but the bigger driver is that combined org structures increase the decision-making velocity of teams. I have written extensively about how the speed of decision-making is the single largest drag on teams when it comes to moving quickly and getting things done. Hybrid executive roles like the CPTO almost completely remove that friction, and companies are leaning in. So why are these roles slowly but surely gaining popularity? For that, we have to go back in time, just a little bit.

I consider the period from 2009 to 2023 the golden era of tech. Contrary to popular belief, unlike financial institutions, tech companies largely escaped the financial crisis. Between 2009 and 2023, tech companies, fueled by the SaaS business model, cloud computing, and a new way to trap customer eyeballs (aka the smartphone), grew like it was nobody’s business. In that same period, they went from owning roughly 10% of the S&P 500 to basically owning it outright.

The products these companies built were truly groundbreaking, and they required specialized talent that commanded a premium price tag to work on those products. Between 2010 and 2023, if you graduated with a computer science degree, it was almost a guarantee that you had three or four offers lined up before you even walked across the stage, with some reaching as high as $200k a year. As the market lapped up what these companies built, so did the headcount and the spending. Between 2009 and 2023, tech companies nearly doubled their spending on technology hires. And as the spending scaled, so did the specialist roles: software engineers, quality engineers, infrastructure engineers, product managers, product marketing managers, content marketers, performance marketers, and specialist managers to manage all of the above. Having a deep specialist bench was a competitive advantage, and boy, did everyone compete.

Then 2020 arrived and turned all of it upside down.

COVID was the worst of times for everyone, except tech. While the majority of the world was hunkering down, the tech hiring frenzy reached fever pitch. As the world moved indoors and online, demand for tech products went up exponentially, and companies responded by overhiring and overpaying. As COVID became a thing of the past and interest rates started ticking up, reality set in. Companies realized that the demand spike of 2020 and 2021 was temporary, which meant the expensive hires they made to meet it were no longer defensible. Then the bloodletting started.

As companies were shedding heads, a game-changing technology made its debut: the AI large language model. An LLM is a type of AI trained on vast amounts of text that learns to predict and generate human-like language. In plain terms, it’s software that has read more of the internet than any human ever could, and can write, reason, and converse as a result. Think StackOverflow or Reddit, but without the condescending tone. Repetitive tasks can now be done by anyone regardless of specialization. An engineer can write a PRD. A product manager can build features and push code. LLMs made the barrier to entry effectively zero.

Which brings us to where we are right now. Tech companies are facing enormous pressure to be financially disciplined and get more out of fewer people, and LLMs are making it easier every day for specialists to become cross-functional. So if it’s easy to learn a different discipline, what role does a functional leader play? The answer is: nothing. That role will disappear, starting with the executive ranks. The future belongs to the cross-functional leader, the general manager.

So, what is a General Manager?

My journey to becoming a general manager started about ten years ago. It was circa 2016, and it was my first day at Amazon as a software development manager. In my first meeting with a peer (hey, Ahmed!), I asked him how things worked at Amazon. One of my questions was who his product counterpart was. His answer: “None. You are the product manager for your team.” It was common at Amazon to not staff every team with a dedicated product manager. Engineering managers were expected to put on the product hat as needed.

In the beginning, it was intimidating. Up until that point, I had very little idea what being a product manager actually meant on a daily basis, but I had no choice but to figure it out. Bit by bit, I learned how to identify an ideal customer profile, connect my team’s work to business outcomes, run customer interviews, build roadmaps, and gather and synthesize feedback. What I discovered along the way was that if you have the will, are genuinely willing to put in the effort, and are humble enough to ask for help when you’re stuck, no technical or functional skill is actually unlearnable.

When I finally started operating as a single-threaded leader for my team, it felt like we had unlocked a new level of productivity and focus, like the feeling when your ears unblock after a steep downhill. Since that day, I have pursued and landed multiple GM roles at Smartsheet, Kickstarter, and now Kajabi. And with the rise of AI and the collapse of barriers to cross-functional learning, I firmly believe the future executive will be a GM.

A general manager is not someone who knows everything about every function. That’s not realistic, and it’s not the goal. A GM is a T-shaped leader with depth in one area, combined with enough working knowledge of adjacent functions to ask the right questions, spot the right problems, and make decisions that account for the whole business rather than just one corner of it.

The other characteristics that matter: a GM understands the overall business, including the financials and the key metrics that signal health. They can get up to speed on a new domain quickly and earn the respect of teams even without deep expertise in what those teams do every day. They know how to hire strong leaders, they know where their own blind spots are, and they hire to fill them. And above everything else, they are relentlessly curious, not performatively but genuinely. That curiosity is what makes everything else possible.

How do you start becoming one?

My journey started at Amazon, but the path isn’t unique to Amazon. There is a specific set of steps you can take that will put you on a clear path to becoming a GM. Covering each step in detail would be too much for this essay, so I will keep it at a high level.

If you are a leader in a tech organization, either responsible for people or projects or both, your primary job is to act as a capital allocator. Every decision you make, especially big ones like hiring someone new or spinning up a new project, should be made through the lens of: will this investment result in positive upside for the company? This deceptively simple question is hard for most leaders to get behind, especially those who haven’t experienced multiple downturns. Voluntarily saying no to new headcount is hard, but that is what will separate future GMs from those who will be managed by one.

The second move is also deceptively simple: start showing up as a broader leader in the rooms you are already in. Most leaders walk into cross-functional meetings to represent their function. They defend their numbers, explain their progress, advocate for their priorities, and go back to their desk. A GM shows up, curious about the whole room. They ask questions outside their lane. They notice when two teams are working at cross-purposes. They volunteer to help with problems that aren’t formally theirs to solve. And if you are asking questions because other leaders are doing the same, or you are deliberately trying to make the recipient uncomfortable (yes, it actually happens), you are doing it wrong. Show up with genuine curiosity and a willingness to help.

The third move is to actually start doing cross-functional work. It isn’t enough to just show up with good questions. When I was at Smartsheet, I wrote PRDs, wrote GTM copy, jumped on customer support calls, interviewed and hired product managers, created user surveys, and a lot more that wasn’t directly tied to engineering deliverables. Pro tip: if you want to quickly earn some cross-functional credibility, volunteer to represent a sister org in a business review. Product managers typically write the status updates and serve as the main person (aka punching bag), fielding questions in business reviews. An engineering leader volunteering to do that for their team is a fast and visible way to start building cross-functional skills.

The penultimate step is to look for spots in the org that could benefit from a cross-functional leader. As I have mentioned in multiple essays and in my book, the single biggest productivity killer is slow decision-making. Look for spots in your org where decisions could be made faster if two functions or teams reported to a single leader. Once you spot those delays, don’t open the conversation by saying “making these teams report to me will fix this.” Start by volunteering to help. If you help unconditionally, good things will happen.

Lastly, raise your hand. More than twenty years ago, when I was working the grill at McDonald’s, my shift manager told me something I have never forgotten. He said, “In America, you will never get anything if you don’t ask for it.” It was true back then, and it is true right now. If you have done your homework and strongly feel there is an opportunity in your current org for you to become a cross-functional leader, ask for it. Best case, you get it. Worst case, you don’t, but you will have the skills to become one at your next company.

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Until next time!

If you are expecting me to reveal that I had a sudden realization of what the right approach was, you are wrong. Sorry. I figured it out after a decade or so in the industry and with a lot of help from my mentors and managers. If you’re a young tech professional feeling frustrated, tired, and burnt out because all your attempts at doing the right thing for your team and your company are not working out, this post is for you. I will break down five things you need to learn to influence your peers and teams.

Eat some humble pie. Young, driven, smart, and humble don’t always show up together. Specifically, humility is almost always missing. This is especially visible when young folks have some experience and have seen some wins. There is a technical term for this phenomenon: the Dunning-Kruger effect. Early competence produces disproportionate confidence. The less you know about a domain, the less you know about what you don’t know. A senior engineer with three years of experience has learned enough to feel like an expert, but not enough to have been humbled by the full complexity of the problem space. That comes later, usually after a few painful failures. Additionally, if you are under 30, your prefrontal cortex, which manages impulse control, might not be fully developed. Low impulse control combined with disproportionate confidence results in you showing up as an arrogant, entitled, all-knowing ass.

There are no absolutes. What you consider an absolute fact might not be the case in five, ten, or fifteen years. This is especially true in tech. Ten years ago, the rage was microservices. All conversations were some variation of, “Why are you not building microservices? You are dumb not to.” Fast forward to now. Turns out monolithic codebases aren’t so bad. Kickstarter and Kajabi both have monolithic codebases, as do Shopify and Google. The current rage is AI. AI for everything is turning out to be not a great idea. It is great for some use cases (coding, for example) and not so great for others (creative content). My point is, when you are positioning something in front of a person or a team, keep in mind that your conviction might turn out to be wrong. So what is the right approach?

Start with listening. Don’t bring a solution without understanding context and history. Before you say, “You should be using <insert_new_tech> for <a_use_case_you_barely_understand>”, start by understanding the landscape. If asked humbly, most people will be more than willing to spend time with you and share their perspective. When you are talking to folks, just listen. Don’t try to interject your solution. Once you have talked to enough people, fully understood the landscape and history, and internalized your colleagues’ day-to-day reality, take a beat and write down the problems you have noticed. Let that sit with you for a bit. If you have slept on it for at least one night and still woke up energized and enthusiastic about solving it, move on to the next step.

Build consensus. It is extremely hard to get people, teams, and leaders to invest energy into solving a problem that doesn’t have broad agreement behind it.

The right way to build consensus is to start by asking your stakeholders what is top of mind for them. What is keeping them up at night? What are their goals? What problems are they trying to solve today? Lead with that. Don’t start with, “Hey, I think this is a problem, do you agree?” Start with, “What is top of mind for you?” or “What is keeping you up at night?” or “What problems are you focused on right now?” If those problems don’t intersect with what you think needs solving, you are going to have a tough time getting people behind your solution.

If everybody agrees the problem is worth solving, raise your hand to be on the team. If someone else gets picked to lead, don’t throw a fit. Just focus on doing a great job. If you come across as someone who was only pushing to solve a problem for selfish reasons, it will erode a lot of trust. Hit your deadlines. Raise risks before they become risks. And if you mess up, own it. Ask for feedback. Raise your hand for the toughest tasks.

Deliver Results - No one will ever listen to the person who has a ton of opinions but has never delivered anything of value. I have encountered these folks even at seemingly well-run teams, including at Amazon. Super sharp, early-career engineers who have a lot of strong, seemingly intelligent opinions but have never actually delivered anything meaningful.

Before you try to push your team to become better versions of themselves, you need a track record of delivery, so that people around you know that you are not just talk and that you can deliver results. Keep raising your hand to participate in mission-critical, time-constrained projects. Show that you can get stuff done. Show that you can walk the walk, not just talk the talk. Then you can go change the world.

Earn Trust - You can only influence people if you have built a level of mutual trust. So how do you earn someone’s trust in a professional setting? Very simple.

You deliver on your promises.

It’s as simple as that. The easiest way to build trust is to do what you said you would do.

Be vulnerable. This one sounds counterintuitive, especially if you are trying to be taken seriously. But stay with me.

Most young professionals have an answer for everything. They never admit uncertainty. They would rather bluff their way through a conversation than say three simple words: I don’t know. And that performance is exactly what makes the old-timers roll their eyes internally.

Nobody trusts the person who always has an answer. People trust the person who knows when they don’t have one.

When you say “I don’t know,” or “I don’t have experience with this, can you walk me through it,” or “help me understand the history here,” it changes the conversation from, “Hey, I want you to do this for me” to “Hey, I need help” and most professionals will almost always help when someone explicitly asks them for it. That is the moment a professional relationship actually begins.

There is also a reciprocity effect worth understanding. When you admit you don’t know something, you give the other person permission to do the same.

One important boundary, though. Vulnerability in a professional context means intellectual honesty. Admitting gaps in your knowledge, asking for help, and approaching problems with curiosity instead of false confidence. It is not the place to dump all your personal emotional baggage on your co-workers. That can misfire very badly.

None of this is easy. It takes longer than you want it to and requires more patience than feels fair. But it works. And if you don’t want to do any of it, start your own company and build it the right way.

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When Leadership and Teams Stop Speaking the Same Language

Every team and the leaders who oversee them start out with the right intent, but over time, there is a real chance their intents and goals diverge to a point where employees and leaders develop a deep mutual distrust.

A great example is the era of social justice causes. When leaning into social causes was en vogue, companies leaned in hard. Capital was also nearly free at the time, so for reasons I can only speculate (cultural cachet, recruiting, brand awareness), companies threw themselves into social causes like it was nobody’s business. All this virtue signalling never amounted to any real change to their bottom lines. All it did was let them score cheap social points. Brand teams leaned into it for social media wins, recruiting used it as a talking point, and so on. The problem was that this was somewhat of a one-way door. Inadvertently, these companies were conditioning their employees and customers to believe they were working for or buying from a social justice champion.

Fast forward to the lean years. Free capital is gone. Something charged happens on the social scene (the ICE raids, or the war in the Middle East, etc). Employees now expect the company to react just like it did before. But leadership is trying to dig out of the COVID-era hangover and would rather its teams focus on the business than spend energy on social causes.

To be clear, I’m not saying companies shouldn’t participate in socio-political discourse. But if they do, they have to be consistent, and their stances need to be codified as a corporate value, not a vibe. The root cause here is poor executive communication about what actually matters. If you are a for-profit company, leaders have to periodically remind their employees what that means: solving for customers, hitting goals, becoming profitable, and keeping investors in mind. Companies can change direction, but when they do, they have to be deliberate about communicating the what and the why. Lastly, leaders should always be very clear about which decisions will be democratic and which won’t be. This way, employees can decide if the company’s values and goals are something they can work with or not.

Poor Ownership and Accountability

Companies often have the tendency to hire smart people for a lot of money and point them in the general direction of a problem. They assume that smart people will work together to break down the problem and solve it. I can unequivocally tell you that doesn’t happen. A version of the bystander effect plays out in companies as well. People assume what their roles are and the problems they should tackle based on their comfort level, but that might not be the best use of their skills at that given moment. Additionally, a lack of clarity around who is empowered to do what encourages fiefdoms. Politically savvy leaders make plays for parts of the problem they shouldn’t be focused on, purely to keep justifying their jobs.

The best leaders are extremely prescriptive about who does what. Sometimes they calibrate incorrectly and veer into micro-management, but a little bit of micro-management is better than throwing a problem at your team and creating the corporate hunger games. Here is a simple framework for determining whether ownership lines are clear: for every employee on your team or in your org, write down their goals for the year. If more than one employee ends up with overlapping goals, you have an accountability problem.

However, if ownership lines are clear and you are still seeing toxic behavior, it might be that you have poor performers with very little ownership. A dead giveaway is when people say, “That is above my pay grade,” or “That is not my job.” To be clear, I am not suggesting that everyone should take on every single piece of work put in front of them, but a high agency person would: 1) not open with “that’s not my job,” 2) if there is a clearly identified owner, point the requestor there, 3) if no owner has been identified, either get the job done if they have bandwidth or escalate to their manager for prioritization help. But they will never say it’s not their job.

Running in Place

Nothing demoralizes a team more than not seeing wins. And winning, in most cases, doesn’t mean meaningful impact to the company’s bottom line. Teams just need to see their efforts manifest as a working product used by real customers, marketing campaigns seeing real results, or services being used by paying customers. In short, they need to see that their efforts resulted in something.

New teams working on zero-to-one initiatives run into this quite a bit. When ambiguity is high, the chances of analysis paralysis are very real, which can lead to stalemates, poor morale, and toxic teams. This is something leaders need to watch out for and intervene on when they sense the team is struggling to ship.

My rule of thumb is to intervene when a team misses its deadlines three times in a row. When I dig in, I usually find the same three culprits: nobody agrees on what to build, nobody agrees on how to build it, and nobody has defined what good enough looks like. My response to all three is basically the same. I make an executive call on direction, and we test our way to product-market fit. If there are no one-way doors, I tell the team to just pick a tool and get the damn thing done. And when people ask how we’ll know if it’s good enough, my answer is always the same: ship it, measure it, fix it.

Performative Caring

This one is more nuanced than it sounds. The leaders who openly treat their employees like cattle are easy to spot and easier to leave. The more insidious version is the leader who genuinely believes they care about their people but whose actions tell a completely different story.

You know the type. They kick off every all-hands with “our people are our most important asset” and then approve a compensation structure that pays below market. They say “my door is always open,” but make you feel stupid for walking through it. They celebrate “work-life balance” in the company handbook and then Slack you at 10pm expecting a response. They throw pizza parties after a brutal quarter instead of asking why the quarter was brutal in the first place. This is performative caring, and employees see through it faster than leadership thinks.

The employer-employee relationship is like a see-saw. What you want is balance, both sides pushing equally, essentially seeing eye to eye most of the time. The minute it overswings in one direction, you get problems. And the particular problem with performative caring is that it creates a specific kind of resentment, one that is harder to articulate and therefore harder to fix. Employees can’t point to a single villainous act. It’s death by a thousand small disappointments that eventually push the employee side of the see-saw way down.

The best leaders I have worked with or observed share one common trait: they are consistent. What they say and what they do are the same thing, whether anyone is watching or not. That consistency, over time, is what builds the kind of trust that makes teams want to go above and beyond.

Why Are They Still Here

Nothing reveals a leader’s true character faster than how long they let a toxic performer stick around. And in most organizations, they stick around way too long. The good people notice. They always do. And when they see someone who is actively making the team worse face zero consequences, they draw a very logical conclusion: leadership either doesn’t see it or doesn’t care. Neither is a good look.

In my experience, it comes down to three things. The first is conflict avoidance. Managing out a poor performer is an uncomfortable, time-consuming process, and a lot of leaders would rather tolerate the dysfunction than have the hard conversation. The second is over-reliance. Toxic performers are often technically strong or have institutional knowledge that makes leaders nervous about losing them. So they make an implicit trade: we will put up with the behavior in exchange for the output. That trade always costs more than they think. The third is denial. Some leaders simply cannot bring themselves to admit they made a bad hire, so they keep hoping the person will turn it around.

The cost of letting toxic performers linger is almost always underestimated. It’s not just the damage they do directly. It’s the good people who leave because they don’t want to work with them. It’s the team members who quietly disengage because they see that bad behavior has no consequences. It’s the cultural signal it sends to everyone watching: this is what we tolerate here.

My rule is simple. Be direct with them about what you are seeing and give them a genuine chance to course correct. If they don’t, move fast. Every day you wait, the damage compounds, and your credibility as a leader takes another hit. The team is watching. They are always watching.

Here is the uncomfortable truth. Most of the things that make teams toxic are not mysteries. Leaders know when communication is broken. They know when ownership is unclear. They know when someone on the team is making everyone else miserable. The question was never whether they knew. It was whether they cared enough to do something about it.

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“What do you mean?” I replied

“This engineering manager I work with…I don’t know what drives his decisions. How do I find out what he is optimizing for?” she replied.

I thought for a second, and I said, “Most people, including leaders, optimize for preserving their jobs”.

Of all the leaders I have encountered in my career, including prior bosses, very few of them explicitly share with everyone what are they optimizing for? What is driving their decisions? Why are they making those choices in that moment? Many leaders, including seemingly successful ones, just stumble through leadership. They move from one project to another, one crisis to another, one performance review to another, never pausing to figure out what is affecting their decisions. And because they never sit down and intentionally decide what broad outcomes they are driving towards, they are unable to explain to their teams why certain decisions were made, which will erode trust.

So this post is about giving leaders a framework for setting their intentions. I will break down the different types of intentions a leader can set, when to set it, how to communicate your intentions with your team, and what the pros and cons of each intention are.

Optimizing for the job.

This is usually the default intention that is hard-wired into most employees, including leaders. When you don’t explicitly decide what drives your decisions, you are subconsciously optimizing for your job. This mostly means making your boss happy and, in some cases, making your boss’s boss happy. Making your boss happy means ensuring all your goals that are tied to their success are top of mind for you.

There are a few scenarios when you have to intentionally optimize for your job. First, during your first 90 days into a new job or a new role. It is extremely important to show real results in the first few months into a new job. Equally important in those initial months is to convert your boss from your manager to your cheerleader. So hitting your goals that will make them look good is pretty important.

The second scenario where you have to do this is when people (or teams, or leaders) have very low trust in you or your team. This could be due to various reasons. Multiple missed deadlines, customer escalations, poorly performing team members, etc. When you are dealing with low trust, you have to pivot back to operating like it’s your first 90 days. You figure out which projects, initiatives, or decisions will help you win back the lost trust. This is also the time to really put the pedal to the metal and push a little harder to see things over the line. Lastly, if your boss hands over some messy business (messy stakeholder conversations, layoffs, etc.) to you to deal with, say yes.

Before we get to the cons, let’s talk a little bit about how to message this to your team. If you are in the first 90-day period, it’s about explicitly communicating to your team what kind of changes you are looking to bring out, which projects are important to you, etc. Most people will be expecting a new leader to make some changes, so don’t hesitate to make deep changes in your first 90 days. You might not get another chance to make changes like that. If you are dealing with a low-trust scenario, communicate that plainly to your team as well. Some leaders shy away from explicitly sharing that message with their teams because they don’t want to demotivate their teams or introduce some weird fixation with perception in their teams. Well, guess what, teams already know. If a team is struggling, its team members are probably the first to notice the shift in perception. Explicitly telling them that there is a problem and also giving them a path out of it will focus your teams in the right direction. If you don’t tell them anything, they will make up their own stories and most likely start to devolve into conspiracy theories, which will bring morale down very quickly.

There is one big con to optimizing for your job. In making the right decision for your job, you might make the wrong decision for the company. Most bosses are rational, but if you encounter a terrible boss, there is a real chance that in making your manager happy, you will make a terrible business decision. The one easy way to hedge against that is to ask for feedback. Ask your peers, your mentors, heck, even your employees. Ask them to poke holes in the plan, and if you feel there are too many holes in the plan, bring it up to your manager. The good ones will take the feedback. The bad ones won’t, and then it’s up to you to decide if you want to disagree and commit or not. I am going to say something controversial now, so bear with me. If you believe that the role, company, team, and industry are something that will asymmetrically benefit you and your career in the long run, execute on your boss’s decision EVEN if it feels wrong to you in the moment.

If you believe you can accelerate your career trajectory in that company/role and/or if you believe success at this company will lead to higher value opportunities in other companies, AND if there are no legal or ethical downsides, execute the plan, even if it feels a bit wrong or uncomfortable in the moment. Also, if the plan doesn’t involve walking through a one-way door, which in reality are most decisions in companies, don’t overthink it, just execute.

​​Optimizing for speed.

Sometimes you have to optimize for speed. Speed of decision making, speed of execution, and everything in between. Basically, how to move from idea to working product in the hands of your customer as fast as possible. This mode of intentionality works when the goals and their outcomes are fairly clear. Put it another way: if you know for sure that delivering X feature will result in delivering Y outcomes (revenue, customer growth, <insert_tech_metrics_jargon>, etc.), it could be very beneficial to optimize for speed. So how does one go about optimizing for speed?

Remove management layers - People managers can be incredibly useful in some operating modes (discussed right after this), but if you are optimizing for speed of delivery, managers more often than not will come in the way. Consider this scenario: Team A has to modify Team B’s code base to develop and deliver their feature. Team A’s manager goes and talks to Team B’s manager. Team B’s manager grumbles and complains about how their roadmap is full (roadmaps are NEVER empty) and tells Team A’s manager that they can’t hit their timelines and asks them to come back in six months. It’s always six months! Team A’s manager escalates to Team B’s manager’s manager and convinces them that Team A’s project has the CTO’s blessing and is very critical to be developed and delivered on time. Team B’s manager’s boss asks Team B’s manager to ‘find’ a spot in the roadmap. Team B’s manager grumbles one more time and reluctantly finds a spot in the roadmap. Team A’s team leads coordinate with Team B’s team leads to make the necessary changes. By the time the feature gets shipped, Elon Musk has sent a manned spaceship to Mars.

Obviously, the above is a very extreme case, but it is very common for mid/large-sized companies to run into a version of this situation all the time. Now imagine Team A and Team B were managed by one manager. The entire back and forth from the example above would be reduced to a decision the singular manager can make in a second. It is not hyperbole to say that removing management layers will increase your decision-making speed by an order of magnitude or higher.

Remove team boundaries - For the longest time, I was firmly in the camp of leaders who believed that small, dedicated teams that focus on one thing and one thing only for an extended period of time are crucial to any organization’s success. This iron-clad belief was completely shattered by the COVID-19 recession and the fallout after that. Long-lived teams work only when you can afford them. If you are upside down financially, or your growth is sputtering, you don’t have the luxury to run multiple teams, give them separate charters, and hope one of them has outsized returns. At Kickstarter and now at Kajabi, I have adopted the mindset of flexible teams with goals that change quarterly. In the day and age where AI tools are dramatically accelerating the productivity of everyone, including an old-timer like me, the ramp-up time for an AI-enabled engineer to quickly understand a new code base is orders of magnitude lower than what it was before. At Kickstarter and at Kajabi, teams have flexible boundaries and goals that change every quarter. To be clear, the goals still ladder up to a vision, but teams are expected to work on whatever is the most important thing to focus on in that moment in time. One quarter could be focused on fixing user experience, the other could be focused on fixing infrastructure, etc. Lastly, this doesn’t need to be all or nothing. You could have X% of your org permanently dedicated to a specific area of the product (for example, infrastructure), as long as you know for SURE that the investment is necessary and will result in the right outcomes for your business.

Clear decision maker - Optimizing for speed only works when there is one decision maker. In most companies, it’s the CEO or someone in the executive team who has been appointed the main decision maker. This is sometimes hard for the org to swallow. Tech companies have been conditioned for a very long time to go bottoms up. That is, teams are given an abstract high-level problem, and teams will come back with projects to solve that abstract high-level problem. If you are going to optimize for speed, this is not going to work. Someone has to say, ‘Don’t think, do this.’ A great example is Steve Jobs, who asked his team to ditch the plastic on the original iPhone in favor of glass because plastic scratched easily. No debate, no discussion. He just ‘told’ the team to execute, which led to the development of Gorilla Glass.

Before I get into the cons of this operating mode, I do want to point out that you, as a leader, can pick and choose which of these operating modes you want the company to adopt. You don’t have to stick with one forever. Figure out what will help the business and pick the right operating mode to go with it. The most important thing is to share with your organization why you are making the decisions. Why did you choose that specific operating mode, and what kind of outcomes are you expecting out of it? Also important is to be honest with your team if your choices don’t pan out. Ok, with that out of the way, let’s get to the cons.

The biggest con of this operating mode, where the management layer is anemic and teams don’t get to focus on one product area, is career growth. One of the consequences of a flat organization is that the career ladder, especially for leadership roles, is very short. If there are only two managers in the entire org, you can’t artificially create a spot for a third one, which means anyone aspiring to become a manager has to be comfortable waiting for a spot to open up, or they end up leaving.

Additionally, in flat organizations, managers have a much wider span of control, which means they can’t pay attention to every single individual in their org. And that means that regular promotions become tricky. Managers won’t have the time to plan out a comprehensive career path for their employees. The burden is now on the employee to figure out how to find the right projects. The manager can certainly guide them, but they won’t be able to do what they would be able to do when their span of control was much smaller. To be honest, I am a big fan of letting employees chart and find their own destiny, but that’s just me.

Optimizing for scale

Or put in another way, “Let’s spend all the money we have and see what sticks”. Just kidding! Still recovering from the post-COVID financial slump. Great, I have already digressed. OK, let’s restart.

In this mode, you are optimizing to grow your organization to work on multiple focus areas with the goal (hope?) that you will uncover multiple new revenue channels, which will ultimately strengthen the company. For example, an enterprise company might invest in starting a consulting arm. A consumer company might invest in standing up a content marketing team, and so on. A great example of a company where this way of operating has paid off in spades is Amazon’s AWS business unit. AWS (Amazon Web Services) lost money for a decade before it became profitable. AWS represents 15% of Amazon’s revenue and about HALF of its profit. Amazon’s bold bet paid off in the long run. So how do you optimize for scale? A lot of what you are going to see is the inverse of what we covered in the previous section.

Small, long-lived teams - I first encountered this at Amazon. A small team that has a clear focus can change the game, provided they are given a long enough runway. Clear goals are critical for these teams. A lot of companies end up spinning up these teams when the money was flowing freely and never gave them clear goals or guidance on what success should look like. The mistake companies made (including many teams at Amazon) was to not scrutinize teams at the end of every year on their performance, including not asking the question, “Should this team exist next year?” Without clear goals and focus, you are just setting money on fire. However, when you do it right, small teams whose focus won’t change every quarter can make an insane amount of progress. In my career, I have seen teams that spun up new lines of business, closed the gap with the competition, paid down technical debt, opened up sales in new geographies, and many other things that significantly changed the trajectory of the company. One of the major cons of the flexible team model is that it prevents you from running long-running experiments. So if you have the money and you want to chart out a path to a blue ocean, you need the power of small, long-lived teams. BUT, with clear goals!

HR Machinery - If you have a flat organization, you don’t need a ton of HR machinery to keep it running. What I mean by HR machinery is: Career ladders, Role descriptions, Interview Guidelines, Manager Coaching, Performance Calibration, HR Business Partners to support managers, etc. However, when you are planning on rapidly adding new individual contributors and leaders to the mix, you need to have a cultural assimilation machine in place that will ensure the people you hire not just fit your culture but are actually furthering the culture and becoming evangelists. Netflix and Amazon are great examples of companies that doubled down on ensuring that everyone at the company is a culture add. This is one area where organizations can get carried away very quickly. If you have decided to scale up your HR machinery, do it methodically. And as the British say, to put a finer point on it, add HR machinery only after you feel sustained pain. If your managers are struggling to build happy, productive teams for an extended period of time, it is time to scale up the HR machinery.

Execution machinery - Large teams need tight process control. You need processes to measure the overall health of the organization, which at a minimum should involve an operations review (to ensure your systems are working well), a business review (to ensure the overall business is moving in the right direction), and a program review (to ensure the critical projects are green).

Before I get into the cons, I do want to point out the obvious. Scaling organizations is not for the faint of heart. It is expensive and messy. Every new leader you bring in will grind the working gears of the company, and in some cases, completely bring things to a halt. However, if your core business is humming and you have the cash to experiment, optimizing for scale for a period of time can result in step function changes. Netflix went from renting DVDs to making TV shows. Amazon went from selling books online to sending satellites to space. Microsoft went from selling office software to running a social media company. If you do it with discipline, scaling up could be extremely lucrative for the company, but it comes with a price.

And if you guessed ‘speed’, you would be accurate. The cost of scaling up is execution speed. Decisions take forever. Teams take forever to sort out conflicts. Managers take forever to get stuff out the door, poor performers linger forever, etc. Even an extremely disciplined company like Amazon cannot compete with a smaller team. A great example is Chewy. Chewy focused exclusively on e-commerce for pets and destroyed Amazon in a specific category. So if you are going to scale up, make sure the payoff is worth the speed you are going to give up.

Optimizing for stakeholders.

This is a sinister variation of optimizing for your job. Specifically, you are optimizing to make a specific group of internal stakeholders happy. Many managers do this to curry favor with stakeholders, executives, board members, etc. If it isn’t obvious, I highly recommend not using this operating mode at all. Yes, it could get you promoted and could get you the corner office you have been dreaming of, but it will almost always come at a high cost. You might aggravate your customers. You might cause revenues to dip. You might annoy and confuse your team, and the list goes on. A couple of managers I have had in the past have used this operating mode and positioned it as a strategic business move to the rest of their team and me, but every single one knew that they were doing it to make an internal stakeholder (or stakeholders) happy.

It is not lost on me that internal stakeholders can often determine your future at a company. Large companies are often political minefields where you might need to make a certain group of leaders or executives happy to earn the license to do the right thing for the company. I know that’s a bitter pill to swallow, but that’s the reality.

The right way to go about this is to educate your stakeholders on the potential impact of their decisions. 90% of the time, this solves the issue, and you can walk your misinformed stakeholders back from the precipice of their bad decision. However, in the other 10%, you have a choice. Either you disagree and commit once and hope your stakeholders learn their lesson after they see their decision crash and burn, or stick with your ideals and exit the company.

If you do find yourself in this situation, communicating this to your team is also very tricky. You can’t tell your team that the obviously bad decision is strategically good for the company. You also can’t tell your team person X is making you do this. What I have done in the past is to position these decisions as experiments. “Leadership has decided to do X, and we are going to try it out and see if Y happens,” or something to that effect. Keep in mind that you can’t keep using this excuse. Your teams will ultimately lose trust in you. To be clear, this is the least desirable mode to operate in, and if you find yourself here repeatedly, it’s a strong signal that either the company culture is broken or you need to find a different environment.

Optimize for competition.

It is very rare for a company to operate in an industry with very little competition. Even if you are the first mover in the space, at some point a smaller, faster company will build a competing product and sell it at a cheaper price point and start to pull customers away from you. If you are constantly losing customers to a competitor, it is time to rally the company around beating your competitor and regaining some or all of the lost ground.

This mode of operating almost always has to be combined with some version of optimizing for speed. You can’t catch up with your competition if you don’t introduce an element of speed and urgency in your organization. When you tell your team that you are going to optimize for beating the competition, you have to clearly explain a few things.

1. What does success look like? Optimizing for the competition is like a sprint, not a marathon. You need to set clear, measurable goals with specific timelines. Is success recapturing 10% market share within six months? Is it launching three features your competitor has before the end of the quarter? Is it matching their price point while maintaining margins? Without concrete success metrics, your team will burn out chasing an abstract enemy. More importantly, you need to define when you will stop optimizing for competition and switch to a different operating mode. This cannot be a permanent state.

2. What are we NOT going to do? When you optimize for competition, you are making a deliberate choice to ignore other things. Be explicit about what you are sacrificing. Are you going to delay that infrastructure project? Are you going to push back on customer feature requests that don’t directly address the competitive threat? Are you going to accept technical debt? Your team needs to know what they can safely deprioritize without getting in trouble later.

3. What is our unfair advantage? A great example of a company that successfully beat back its competition is AMD. For over a decade, Intel dominated the CPU market while AMD struggled in the background, losing money and market share. But in 2017, AMD launched its Ryzen processors built on a completely new Zen architecture. AMD’s unfair advantage was its willingness to completely redesign from scratch, while Intel kept iterating on old architectures. AMD also maintained motherboard compatibility across generations, while Intel forced customers to buy new motherboards with every upgrade. Within seven years, AMD went from irrelevance to capturing nearly 30% of the desktop market and overtaking Intel in datacenter revenue for the first time ever. AMD didn’t try to beat Intel at Intel’s game. They found their own game and played it better.

Before I get into the cons, I want to be clear about when NOT to use this mode. Don’t optimize for competition when you don’t actually understand why customers are leaving. Don’t optimize for competition when your competitor is simply better capitalized, and you’re going to lose a war of attrition. And definitely don’t optimize for competition when your real problem is that your product sucks or your customers don’t actually want what you’re selling. Fix your product first, then worry about the competition. Also, never forget that this operating mode is a sprint, not a marathon.

The biggest con of optimizing for competition is that you will lose sight of your customers. When you are laser-focused on what your competitor is doing, you stop listening to what your customers actually need. You start building features because your competitor has them, not because your customers want them. You start making pricing decisions based on undercutting your competitor, not based on the value you provide. You might win the battle against your competitor and still lose the war because your customers have moved on to something completely different. I have seen companies spend millions of dollars building features to match their competitors, only to realize their customers didn’t care about those features at all. They cared about something entirely different that neither company was paying attention to. So if you are going to optimize for competition, make sure you have someone on your team whose entire job is to keep reminding everyone what your customers actually want.

Optimize for reducing cost.

One of my all-time favorite movies is Goodfellas, and my all-time favorite line from the movie is when Henry Hill tells the audience, “Every once in a while, I’d have to take a beating. But by then, I didn’t care. The way I saw it, everybody takes a beating sometimes.” He is absolutely right. Everybody takes a beating sometimes, and companies are no different.

Companies are run by people, and people are flawed. Some more than others, but people (including me) make dumb choices all the time. Additionally, capital markets are completely unpredictable in the short-term (1-5 years) and may be somewhat predictable in the long run (5-10 years). If you combine flawed decisions made by flawed people with unpredictable markets, you get recessions and downturns, which require companies to make drastic changes, including cutting down their expenses. Sometimes companies have to do it to save themselves, other times their board forces them to make changes, but the bottom line is, at some point, companies will have to figure out how to cut costs. If you do end up needing to optimize for cost, this is the way to do it.

If you google how to cut costs at a company, every article will tell you to start with software subscriptions, professional services, travel expenses, etc. The reality is, none of these will meaningfully affect your bottom line. People are the largest expense for every company on the planet. Starting with anything else is just delaying the inevitable. Start with your personnel costs first. To be clear, I am not saying that tightening your subscriptions or travel costs is a bad idea. You should do that as well, but remember that savings will only come from cutting personnel costs. I know this sounds harsh, but it is the reality. So, figure out how much you want to save, start with a 10% cut, and work your way up from there. The key is to cut deep but do it once.

The key to landing this message with your team is to be honest about the financial reality your company is facing, BUT also show them a path out. Show them how the company will get out of the hole it is in and show them how you will restart growth. If you don’t give your team hope, you will most definitely start a downward spiral in your company where nobody is motivated to keep pushing and will most likely stick around until they find their next job and leave.

The cons of cutting costs are basically everything. Company morale takes a dive. Velocity slows down. Career development takes a backseat. The company loses its competitive edge. Depending on how deep the company cuts, it could affect the product roadmap, which could cause customers to leave. However, if you are intentional about this change and ensure this is a temporary blip in the company’s trajectory with a path to growth right around the corner, your company will bounce back.

Framework

Here is a reference framework that captures the core principles of the essay. Feel free to print it out and keep it handy!

OPERATING MODE: Optimize for Job

• When to Use: First 90 days in new role; Low trust situation; Boss hands you messy business

• How to Execute: Focus on goals tied to boss’s success; Deliver quick wins; Convert boss to cheerleader

• How to Communicate: Be explicit about changes you’re making. If low trust, tell team plainly and give them path out.

• Duration: 90 days - 6 months

• Biggest Con: Might make wrong decision for company while making boss happy

OPERATING MODE: Optimize for Speed

• When to Use: Clear goal with known outcome (X feature = Y result); Need fast execution; Certainty over experimentation

• How to Execute: Remove management layers; Remove team boundaries (flexible teams); One clear decision maker (”Don’t think, do this”)

• How to Communicate: Explain why this mode, what outcomes expected, be honest if it doesn’t work.

• Duration: 3-9 months

• Biggest Con: Career growth suffers (short ladder, wide span of control, employees must find their own path)

OPERATING MODE: Optimize for Scale

• When to Use: Core business is strong; Have cash to experiment; Want new revenue channels

• How to Execute: Small, long-lived teams with clear goals; Build HR machinery (after sustained pain); Build execution machinery (ops/business/program reviews); Annual team review: “Should this exist?”

• How to Communicate: Show the vision. Explain the long-term bets you’re making.

• Duration: 1-3+ years

• Biggest Con: Execution speed tanks (decisions slow, conflicts drag, poor performers linger)

OPERATING MODE: Optimize for Stakeholders

• When to Use: Political minefield; Need stakeholder buy-in to do right thing; WARNING: Avoid if possible

• How to Execute: First: educate stakeholders (works 90%); If that fails: disagree & commit once OR exit; Position as “experiments” with team

• How to Communicate: Can’t say decision is bad OR blame person X. Frame as “Leadership decided to try X to see if Y happens.” Can’t overuse this.

• Duration: As short as possible

• Biggest Con: This is least desirable mode. If repeated, culture is broken or you need to leave.

OPERATING MODE: Optimize for Competition

• When to Use: Losing customers to specific competitor; Competitor has clear advantage; Need to regain ground

• How to Execute: Combine with Speed mode; Set clear success metrics & timeline; Define what you WON’T do; Identify your unfair advantage

• How to Communicate: Explain: What is success? What are we NOT doing? What’s our unfair advantage? When will we stop this mode?

• Duration: 6-12 months (sprint, not marathon)

• Biggest Con: Lose sight of customers (build what competitor has, not what customers want)

OPERATING MODE: Optimize for Reducing Cost

• When to Use: Running out of money; Board demands cuts; Business fundamentals changed

• How to Execute: Cut personnel costs first (biggest impact); Cut deep, do it ONCE; Also cut projects & vendors; Start with 10% and go up

• How to Communicate: Be brutally honest about financial reality BUT show path forward. Give hope. Acknowledge survivors. Give permission to leave if they don’t believe.

• Duration: 3-6 months max

• Biggest Con: Everything (morale tanks, innovation stops, tech debt piles up, customers suffer, best people leave)

KEY PRINCIPLES:

• You can switch modes as situations change

• Some modes combine (Competition + Speed), others don’t (Speed + Scale)

• Always communicate WHY you chose this mode

• Be honest when your choice doesn’t work

• Most modes are temporary except “Optimize for Job” (the default baseline)

Conclusion

So when my wife asked me how to figure out what her engineering manager was optimizing for, the real answer is simple: most leaders don’t know themselves. They stumble from decision to decision, crisis to crisis, never pausing to be intentional about what they’re trying to achieve. Their teams are left confused, trust erodes, and opportunities are missed.

But you don’t have to be most leaders.

Pick your operating mode based on what your situation demands. Communicate it clearly to your team so they understand why you’re making the choices you’re making. Execute with conviction. And when the situation changes, have the courage to switch modes and tell your team why.

That’s what separates intentional leaders from everyone else. Not that they always make the right call, but that they know what they’re optimizing for and can explain it. And when they get it wrong, they admit it and adjust.

Your team deserves that clarity. More importantly, you deserve the clarity that comes from knowing exactly what game you’re playing.

Until next time!

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Before we dig into how to build executive presence, let’s quickly unpack what executive presence actually is. A quick Google search will reveal many explanations of what executive presence is, but to put it simply, you have executive presence if people, regardless of how high up the hierarchy they are, listen to you when you speak. You are able to hold the room’s attention if you want to. It’s as simple as that. If people listen when you speak up, you have executive presence. Let’s now unpack how to develop executive presence.

Be well read - The prerequisite for holding a room’s attention is being well-read—and I don’t mean just in your field. If you’re an engineer wanting to develop executive presence, understanding engineering concepts isn’t enough. You need knowledge in every field your company relies on to run: marketing (brand and product), product, finance, legal, etc. Think about the executives you’ll be in the room with and build up knowledge in each of their disciplines. I’m not suggesting you get a PhD in every field, but read at least a book or two about each. If books aren’t your thing, online courses, podcasts, and masterclasses can quickly help you develop a broader worldview.

Why bother? Because your presentations become exponentially more interesting when you can weave in how your idea affects other disciplines. If you pitch an engineering project to the executive team and purely focus on engineering benefits, you’ll lose half the room. But if you call out how it impacts customers, how the company might market it as a feature, how that feature could affect pricing, and any legal implications, you’ll pull in the entire team. Do this a few times and the executive team will automatically start listening when you speak—they might even ask you to join meetings when they’re making big decisions. And if you want to really stand out, become well-read in general topics. Read the news (both left, right, and center), political books, autobiographies, fiction, leadership stories, other essays from this substack (I had to!), historical accounts, and everything in between. I would even go one step further and say watch TV. Yes, watch movies, shows, documentaries, and for bonus learning, watch movies or shows that are in a language you don’t understand. Bottom line, the broader your knowledge base, the more valuable your perspective becomes and the faster you can convince people to listen to you.

Be well put together - Just like nobody takes health advice from an unhealthy-looking doctor, nobody will listen if you don’t make an effort to care about how you show up. I don’t mean you need expensive clothes and jewelry—you need to show up like you care about yourself. Clean clothes, well-groomed, good posture, firm handshakes, strong eye contact. I’ve seen countless people fail to make an impression because they didn’t put in the bare minimum effort for a high-stakes meeting.

Some of you are probably thinking: shouldn’t we be inclusive of everyone, regardless of how they show up? To an extent, yes. But if you’re trying to convince a group or make an impression, you need to reduce the friction between you and your idea. Make it easy for the group to come over to your side. The way you show up is half the battle—don’t let your appearance become a distraction from what you have to say.

Be aware - I remember this one time, a very smart engineer tried to pitch a new service idea to me. I don’t remember the specifics, but it involved breaking apart a problematic part of the monolithic application that was currently running in production and pulling it out into an independent service that would allow the engineering team to scale it more efficiently. The problem was real, the solution was well-thought-out, and that engineer had a track record of delivering results. I couldn’t green-light the project.

The mistake the engineer made was not asking me before he went and did the analysis, what is top of mind for me? What are the things that are keeping me up at night? If he had, I would have told him that the single most important issue I wanted to solve (in that moment in time) was to thwart off a competitor who was taking away market share from us. It wasn’t just me; the entire executive team was constantly thinking about this competitor and how to keep them at bay.

One of the key skills to hone if you want to develop executive presence is to figure out whether the problem you’re trying to solve has ripened enough. And the easiest way to figure that out is to talk to the executives regularly. Every executive (including me) is usually pretty generous with their time and can’t shut up if you ask them what’s keeping them up at night. But even if the executives at your company are not that generous with their time, pay attention to them when they speak up in meetings, AMAs, all-hands meetings, etc. The more aware you are of how the leadership at your company looks at the business world, the better prepared you will be when you have to go in front of them to convince them of something.

Be well spoken - So you have done everything. You are well-read, you are aware, well put together, and you are now about to start speaking. Do you need to get trained in public speaking to finish your executive presence arc? Public speaking training won’t hurt, but it isn’t necessarily required. To grab the room’s attention, you have to do the following:

1. Tell stories. Audiences love hearing narratives. When you speak about any topic, tell a story. Start with the beginning. Set the stage (explain the background), introduce the main characters (the main problem) in the story, move on to the core conflict (why solving the problem is important), and end with a grand climax (how solving it will help the business) when the protagonist defeats the antagonist despite all odds. If you can present your thoughts in a relevant, coherent, and easy-to-understand manner, you can get the room to pay attention.

2. Reduce verbal graffiti - Most people have the tendency to bridge their sentences with ‘uhhh’, ‘ummm’, ‘like’, ‘so’, etc. These words are filler words and will only distract the listener from your core message. When you want to bridge your sentences, try pausing, finishing, or using a transitional phrase (e.g., ‘What I mean by that’) to continue your narrative. Earlier in my career, I would lean very heavily on ‘so’ to bridge my sentences. Heck, even now, if I don’t pay attention to what I am saying, I will subconsciously bridge sentences with ‘so’. What has helped me speak more clearly, without filler words, is to record myself talking, spot the filler words, and then practice pausing or other transitional words to bridge sentences. There is no magic here besides practice. Additionally, pausing has the additional benefit of making your audience lean forward to listen to you. Try the following at work. Say half a sentence, and wait for the audience to automatically lean in to hear what you have to say next. Presidents, statesmen, and world leaders all use the pause to reel in their audiences.

3. Say fewer words - I know your brain is telling you to keep filling the silence with words, but resist it. Just say enough words to get your point across and wait for the room to process it and come back to you with clarifying questions. If you say more than needed, your core idea might be lost in the noise, and you will lose the room. It’s best to be known as the person who says a few well-thought-out sentences rather than the one who can fill awkward silences the best. Embrace the awkward silence!

4. Listen - The best way to learn how to speak well is to listen to how others do it. Watch other executives and leaders work the room. Watch public figures speak on stage. There are numerous public leaders who are worth learning from. A fantastic example is David Attenborough. Every word he says in the background of his documentaries is deliberate, thoughtful, and designed to make the listeners lean in.

That’s it! Executive presence can be systematically learned—I’ve done it, and I’ve helped other product and engineering leaders do it too. If you want to work on yours, I have a few coaching spots open. Reach out at info@maheshguruswamy.com.

There is a word in Tamil called “Rosham” (pronounced ROH-shum). Google translates this incorrectly to “Rage” in English. The correct translation, or at least how it’s used locally where I grew up, is “A raging sense of high pride.” If anger and pride had a baby, that baby would be called “Rosham.” In the moment when my manager told me that I got fired, I felt a sense of hopelessness and despair, but it quickly dissipated, only to be replaced by “Rosham.” I didn’t come here to chilly Wisconsin, all the way from Chennai via Detroit, on borrowed money that my middle-class parents squirreled away by saving every penny for decades, to feel helpless. In that moment, I leaned into my pride and ego. I decided then and there that I was never going to be shit. I was never going to be helpless. I am in control of my future, and circumstances be damned. There is no ceiling. This post is about how to lean into ego the right way.

To a large extent, my Rosham was forged in Detroit. I grew up average in an average middle-class neighborhood. Average in academics, average in sports, no clear destiny. But I knew one thing: I wanted freedom, to live life on my own terms, and America was perfect for that. America offers oversized rewards for individual excellence and perseverance. I wasn’t that smart, so I flipped burgers in Detroit to make ends meet. I graduated into a terrible job market. Many of my friends went back to India. I didn’t, because going back would mean accepting failure. I stuck around and found the job I got fired from. My point being, at every moment of hardship, we all have a choice: declare failure and become depressed, or lean into our ego and declare that failure means nothing. It doesn’t define you. All this failure has done is strengthen your Rosham.

After getting fired, I found a new job and hit the books. I spent hours reading the existing codebase. I actively sought out help from others. I didn’t turn down any tasks. I met all my deadlines. What I realized: when sufficiently motivated (which I was!), I was a quick learner and even quicker at producing results. I wasn’t the smartest person in the room, but I could outperform everyone because I took the fastest path to completing tasks. And to my surprise and delight, that’s what companies wanted. This is where I learned that producing results will always surpass academic purity or perceived smartness in corporate America.

So with my Rosham fully activated, I climbed. When the world around me told me I had to “put in time” to get promoted, I ignored it and job-hopped to that promotion. I made lateral moves while on a work visa—moves that cost me 5-7 years of delay in getting my permanent residency in the United States. I took risks. I joined small startups. I quickly left toxic workplaces. I built strong professional relationships along the way. I made counterintuitive career turns, all the way to a C-suite role.

Rosham powered all of these professional twists and turns. Not the white-hot rage from that Wisconsin apartment, but something steadier. A quiet, consistent refusal to accept someone else’s ceiling as my own. However, if you don’t control it, Rosham can push you down a dark path. Here’s how to harness it without self-destructing.

Convert Failure to Fuel

Rosham is fantastic at converting failure to fuel, but the key is to keep the anger part under control. When you fail, or your team fails, let Rosham swell inside you, but do not let it overtake you. Let it swell and simmer down. Let the anger get to you, but only for a millisecond, and never let it consume you. Once it has simmered down, first tell yourself, “Failure is not the end. It is just the beginning.” Then tell your team, “We can’t let this failure demoralize us. Let’s regroup, let’s learn from the experience, and let’s go win next time.”

Because anger is a big part of Rosham, you have to figure out how to keep it in check. A great way of keeping your anger in check is meditation, specifically mindfulness. However, you can’t let your sense of pride go away. A fantastic way of keeping your pride and ego sharpened and pointed in the right direction is to cultivate a sense of competition—but compete with yourself, not others. For me, that meant health. After a health scare many years ago, I channeled my competitive energy into the gym, running, and weightlifting. When I’m pushing myself physically, that competitive fire stays sharp but doesn’t poison my relationships at work. Bottom line is, to be able to use Rosham effectively, you need to calm your mind down but cultivate your competitive spirit.

Conversely, if your Rosham causes you to blame others, or circumstances, or god, or you lash out at your team, you are doing it completely wrong. I have seen many senior leaders fall into this trap. They viscerally feel the failure (which is good), but they react to it by yelling at others (not so good) or belittling others. Here is a simple test to apply to yourself. In moments of failure (or any crisis), does your team seek you out for support and solutions, or do they dread to talk to you and try to avoid talking to you as much as possible? If it’s the former, you are using Rosham correctly.

Ignore Ceilings and Take Risks

The first time I encountered a ceiling was when I asked my boss what it would take to become a manager and was told to “put in the time.” I tried to convince them that I had cultivated many of the skills that would enable me to succeed as a manager—leading a team, resolving conflicts, translating goals into projects—but it fell on deaf ears. Everybody was sympathetic and agreed that I had the skills, but no one was willing to take a chance on me, mostly because there were others waiting in line. I was on a work visa, and the safest thing for me to do would have been to stay put and “put in the time.” I remember this one conversation where my boss was trying to explain to me why I wasn’t “ready” to be a manager, and in the moment, I let pride and ego wash over me. I said to myself, “Life is too short.” I decided to just roll the dice. I looked around for a new job where I could be a manager, interviewed at a bunch of places, and finally found a manager (thank you, Jeff!) who took a chance on me. The pay was lower, but it gave me the title and the chance to be a manager. Everyone around me, except my wife, told me I was making a mistake. Jumping around pushed out my permanent residency by about five years, but I don’t regret it one bit. That touch of pride that pushed me to take risks took me to places I would have never imagined in my life.

There is, however, a dark side to this. The wrong way to use pride and ego is to let it cloud your ability to be self-critical. Yes, I told myself, “I can become a manager,” but I never told myself, “I have all the skills needed to become a successful manager.” Even though I leaned into my ego in the moment, I never had any illusions about the skills required to become a successful manager. I knew that I had to be self-critical and never lose a sense of humility and lifelong learning.

Take on Impossible Tasks

My next job after getting fired was at a financial services company, and I actually did pretty well there. I became quite the popular developer in both my team and my sister teams for one primary reason: I very rarely said no. I was regularly sent in to pinch-hit and save projects. One of the biggest reasons I rarely said no was because I liked the success and validation from my peers and managers, and it further fueled my Rosham. It pushed me to take on riskier and riskier projects.

Until I found my limit and failed spectacularly. One can only go so long surviving on Red Bull and three hours of sleep. I took on a project I couldn’t deliver on time. My boss was understanding. The project was already plagued with issues before I got put on it, so he was somewhat prepared for delays—but I learned my lesson: I can’t say yes to everything. I had leaned into my Rosham too much without understanding other constraints, which in my case was sleep!

My point being, leaning into your ego to push ahead is a great tactic, but you have to do it smart:

1. Understand your limits. This comes mostly from practice and experience. But the key here is to push yourself first to find your limits, and when you find them, calibrate your yes/no responses to impossible requests accordingly.

2. Be transparent about odds, not outcomes. Giving it your best shot is different than promising success. If you’re taking on a seemingly impossible task, be clear about what to expect from the effort. People will always respect someone who tries versus someone who promises success and fails.

Wrapping Up

Over the last fifteen years, the tech industry has championed empathetic leadership, and that’s largely been a good thing. But I’ve noticed a side effect: a generation of managers who are all listening, all forgiving, all democratic, and completely non-competitive. Their teams love them, but their businesses don’t move. They have empathy without edge, kindness without drive.

The tech world is growing up, and that means its leaders need a backbone. Having a backbone doesn’t mean being a dick. It means knowing when to lean into your Rosham in a productive way—to push back on mediocrity, to refuse arbitrary ceilings, to convert failure into fuel instead of excuses. It means balancing empathy with competitive fire.

Rosham took me from that tiny Wisconsin apartment to places I never imagined. It cost me years and comfort, but it gave me control over my own ceiling. If you’re waiting for permission to bet on yourself, this is it. Let your Rosham rise, but keep it sharp, controlled, and pointed in the right direction.

And that is it for now. Until next time!

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OK, so the ‘thing’ everyone is feeling is the end of a boom cycle that started in the early 2000s, when the internet exploded into people’s living rooms and onto their personal computers. The end of the boom cycle for tech doesn’t mean the end of tech. This is tech growing up and maturing as an industry. Which means the same rigor the market applies to established industries like healthcare, finance, and auto will now be applied to tech companies as well. Market rigor almost always comes with belt tightening, more measured valuations, and market consolidation, because, unlike in the early and mid-2000s, not every tech company can just IPO anymore. I have been in this industry since the early 2000s, and I have gone through these cycles as both an engineer and an executive, so this post is my analysis of what happened, why, and some lessons I learned along the way. But here’s the irony: it doesn’t matter how many people write about this, we’re probably going to repeat our mistakes anyway. Humans are flawed creatures. But if this helps at least one current or future leader, it’s mission accomplished for me. So, let’s get into it.

Early 2000s: The Internet Gold Rush

Most people think the tech industry was born in the early 2000s, but that’s not exactly true. The tech industry has been around for at least 60 years before that. Microsoft and Apple were founded in 1975 and 1976 respectively. From the 1980s to 1990s there was a boom in the personal computing space. What really exploded in the early 2000s was internet-enabled companies, and that’s why most people associate this era with the birth of tech.

The boom cycle was kicked off by Netscape, which went public in 1995. Its stock exploded at launch. The thing to remember is that an internet-enabled world meant globally available products, globally available workforces, and global trade. The world suddenly felt way, way smaller than just a few years before. After Netscape crushed its IPO, the market just gobbled up any business that was internet-enabled. No customers and no growth? No problem. The venture capital industry poured billions into so-called internet-enabled businesses. Then came the crash.

It wasn’t just one thing, but rather a series of troubling events. Companies like Microstrategy had to restate their financials. A bunch of high-profile companies like Pets.com, eToys, and Webvan started failing because their core products didn’t really hit product-market fit. News articles started publishing the reality of how most tech companies had only a year or so of runway left. All of this caused the NASDAQ to wipe out about 75% of its value between March 2000 and October 2002.

2002-2009: The Lean Years

This was a tough time. Tech was still reeling from the dot-com bust, and tech jobs were extremely scarce. The companies that survived, like Amazon and eBay, became extremely disciplined about how they spent money. However, there was a very bright silver lining. From the ashes of the 2001 fire arose many of the companies we love and adore. Facebook, YouTube, and Twitter all launched between 2004 and 2006. Google IPO’d in 2004. AWS debuted in 2006 and kicked off the cloud revolution. The iPhone debuted in 2007, kicking off the mobile revolution. In general, I categorize this time as when tech decided to stop crawling, stand up on two legs, and start walking. Tech CEOs and founders now knew how to build technology products that solved a pain point versus being a novelty like it was in 2001. They had a better sense of how to price their products. They figured out distribution, marketing, and support channels. And things were great, until a few Wall Street geniuses decided to sell debt as securities. Welcome to the 2008 financial crisis.

2009-2015: Free Cash for Everyone!

I’m not going to go into why the financial crisis happened, but here’s the one-line summary: Wall Street pushed people to buy houses beyond their financial means through subprime mortgages, sold those mortgages as securities in the open market, and when people started defaulting, the market blew up. The financial crisis was nastier than the dot-com bubble because it affected almost the entire Western world. Global banks that controlled most of the world’s wealth, Lehman Brothers, Wachovia, Bear Stearns, all went under, and almost ALL the major US banks like Goldman Sachs, Wells Fargo, and Citigroup were under threat of collapse. An extreme example: Iceland lost 25-40% of its pension funds because they were invested in securities backed by subprime mortgages. I used to work at Fidelity Investments when the crisis hit and it resulted in about 3,000 job cuts. I vividly remember my boss back then clearing out his cube just to mentally prepare for being let go.

This is when the government decided to step in and bail the banks out. This is the point in the essay when free market absolutists will say the government shouldn’t have intervened. I don’t have a strong opinion on it, but I do know that if the government didn’t do anything, it would have caused a dramatic collapse of the US financial system, emptying people’s 401ks (my tiny 401k was cut in half in 2009), putting people out of their houses, the works. But maybe that’s the cost of capitalism? Anyway, I digress. The bottom line is, the government intervened. They bailed out the banks using TARP (Troubled Asset Relief Program), where they purchased stocks in these troubled banks and injected capital into them, which gave them the runway to recover. Along with TARP, the US Federal Reserve introduced ZIRP. ZIRP stands for zero interest rate policy, which basically meant it was very cheap to borrow money in the US. Easier borrowing means more spending which means accelerated economic growth that helped push the US out of the financial crisis.

ZIRP made ‘safe’ investments like Treasury bonds pay almost nothing, like 0.5% instead of 5%. So institutional investors like pension funds and endowments needed to find returns somewhere else. That money flooded into venture capital. And where did venture capital invest all those dollars? Tech companies.

2015-2020: Growth at All Costs

Tech companies largely escaped the financial crisis for two reasons. First, they’d just gotten slapped in the face by the dot-com bust, so in 2009 tech companies were more disciplined. Second, tech companies weren’t heavily invested in subprime mortgages. Tech quickly became the industry where all the venture capital money started flowing, which resulted in massive growth between 2009 and 2020. Right around 2015 is when tech companies forgot the dot-com bust and decided to forgo financial discipline for growth. It was growth at all costs and the market rewarded them for it. My theory as to why tech forgot the lessons of the past is that this time around, the founders and CEOs were from a different generation, specifically millennials. These were the millennial founders who founded companies like Snap, Reddit, Kickstarter, Uber, etc. Different generations, different points of view. These millennial founders exchanged suits for t-shirts and business plans for experiments.

A great example of ZIRP-era excess is WeWork. At its peak, the company was valued at $47 billion. In 2023, it declared bankruptcy. Why? Because WeWork was losing $1.9 billion per year, more than its entire revenue. The business model never made sense, but in the ZIRP era, investors didn’t care. They didn’t care until COVID came along and punched everybody in the face.

2020-2022: The COVID Frenzy

COVID was brutal in so many ways. Outside the fact that it killed millions of people worldwide, it introduced a level of instability in the capital markets that we’re still working to stabilize. In the blink of an eye, most of the world went remote. And what do remote workers need? Tech, and lots of it. They needed software that enabled them to work remotely: Zoom, Meet, Teams, Slack. They needed e-commerce services that delivered stuff to them: Amazon, Walmart, DoorDash. They needed gig workers to support delivery companies, and so on.

The Fed had ended ZIRP in 2015, but once the coronavirus upended our lives, they reintroduced ZIRP and more! They brought rates back to zero, introduced massive stimulus packages to help businesses affected by COVID, and pumped trillions into the economy. Remember the tech companies that started forgetting how to be disciplined in 2015? They went completely berserk during COVID. The valuations for tech companies exploded through the roof. Markets were pricing companies at 20 times their revenue, which was unheard of. The singular theory that everyone was basing all their investments on, which included hiring more talent, was that the demand COVID created for tech would continue to stay, if not grow.

It’s also worth remembering the Great Resignation that happened in 2021-2022, which greatly contributed to companies overhiring during that period. For the uninitiated, the Great Resignation was when about 47 million people voluntarily left their jobs in 2021, followed by another 50 million in 2022. COVID ushered in remote work, and that, combined with ZIRP, meant that tech companies were desperately looking to hire more talent, which meant people could easily switch jobs. One day you could be working for a company in California, the next day you’d be working for a company in Massachusetts. Because talent was so hard to come by during 2021-2022, tech companies massively widened their pay bands to attract people. And the thing about salaries is that they always go up, never go down.

So to summarize: between 2020 and 2022, tech companies, fueled by ZIRP and remote work, hired overpriced talent they didn’t need, based on growth projections that assumed COVID demand would last forever.

2022-2023: The Reckoning

But that didn’t happen. If you think about it now, of course, the demand for tech products was going to go down after COVID. COVID was an anomaly. It was not a permanent reset in consumer or economic behavior. In March 2022, the Fed started raising interest rates to combat inflation, which by the way is the negative side effect of ZIRP. When capital is flowing freely in the markets, inflation goes up. ZIRP was over. The free money spigot that had been open for over a decade turned off. When demand reset and interest rates spiked, tech companies figured out that all their growth projections from 2020 were wrong. Valuations crashed to earth. Companies that had built bloated organizations between 2020-2022 couldn’t sustain them anymore, and with investors suddenly demanding profitability for the first time in years, the bloodletting started.

Present: The AI Bubble (Or Is It?)

Welcome to 2025, where things are good but somehow still bad. If there is one word to describe the current tech world, it would be AI—AI, LLMs, vibe coding, take your pick. It is undoubtedly the era of AI. So have investors learned from their mistakes in the past? Heck no. Even though everyone (especially investors on LinkedIn) will argue that AI companies are appropriately priced because of their potential future growth, I would argue that the exact same thing happened during the dot-com and COVID eras. Tech companies were dramatically overvalued during those boom times, just like AI companies and AI-enabled companies are currently overvalued. All it would take is one minor downturn to completely explode everyone’s balance sheets.

And here’s the kicker: the so-called productivity gains that everyone associates with AI have just not materialized yet. AI is making the existing workforce more productive, but it doesn’t come close to replacing an entire person. All the companies that are laying off are not downsizing because they’ve found tremendous productivity gains by using AI. They’re predominantly doing it because they’re still dealing with the hangover from the COVID-era mess.

However, the overvaluation of companies is not across the board. Overall, tech companies have grown up since we first encountered them in the ‘90s. Even though the CEOs still wear t-shirts, they’re paying more attention to business basics like profit margins. Lean, focused teams are back in vogue. Tech companies are becoming mature businesses. What happened to financial companies in the decade before tech is now happening to them. Tech companies have finally grown up.

What This Means for You

So what does all of this actually mean? Whether you’re a founder, an employee, an investor, or someone just trying to navigate their career in tech, the maturation of this industry has real implications for how you should think about the next decade.

If you’re a founder or executive:

The days of “we’ll figure out monetization later” are over. Your investors want to see a path to profitability, not just growth. This doesn’t mean you can’t raise capital or build ambitious companies. It means you need to build real businesses. The market will reward companies that can demonstrate sustainable unit economics, not just virality or user growth. The question is no longer “how fast can you grow?” but “can you grow and make money doing it?”

This also means the talent war is over, at least for now. You don’t need to compete on compensation bands anymore. You can actually build teams based on mission, culture, and the work itself. Use this window wisely. Hire people who want to build something that lasts, not people chasing the next equity lottery ticket.

If you’re an employee:

Job security in tech is no longer a given. The social contract between employer and employee fundamentally changed between 2020-2023, and we’re still figuring out what replaces it. Don’t assume your company will be around in five years just because it has a big valuation. Ask hard questions: Is this business profitable? Does it have real revenue? Can it survive without raising another round?

Also, diversify your skills and your income. The era of specialization, where you could be a “growth PM” or a “React developer” and coast on that for a decade, is ending. The market wants people who can wear multiple hats and deliver business outcomes, not just execute within a narrow domain. And if you’ve been thinking about a side project, consulting, or building something of your own, now is actually a great time. The barriers to entry are lower than ever, and the bloated companies are creating opportunities for leaner, scrappier alternatives.

If you’re trying to figure out where AI fits:

AI is real, but it’s not magic. It’s a tool, like the internet was a tool, like mobile was a tool. The companies that will win are the ones that use AI to solve actual problems and create real value, not the ones that slap “AI-powered” on their pitch deck and hope for the best.

The bigger picture:

Tech is no longer the “new kid” industry. It’s establishment now. That means it’s subject to the same market forces, the same scrutiny, and the same expectations as every other mature industry. This isn’t a bad thing, it’s just different. The Wild West era is over. What replaces it is an industry that’s more stable, more predictable, and frankly, more boring. But boring isn’t bad. Boring means you can actually plan for the future. Boring means companies that build real value can succeed without needing to be the next unicorn. Boring means careers in tech can be sustainable, not just a series of boom-and-bust cycles.

The question isn’t whether tech will survive this transition, it will. The question is: will you? The people who understand that the game has changed, who adapt to this new reality, who focus on building real skills and real value—those are the people who will thrive. The ones still chasing the 2020 playbook are going to have a rough decade.

So here’s my advice: assume the music has stopped. Assume capital will stay expensive. Assume your company needs to justify its existence with actual profits. Assume AI won’t save you from bad business fundamentals. And then ask yourself: given all of that, what should I be doing differently?

That’s what this means.

Observations

So what are my observations from being both a passenger and driver during tech’s maturation cycles?

On Cycles and Memory

• Each generation of founders believes “this time is different,” but the pattern repeats: easy capital → growth at all costs → reality check → discipline. The specific technology changes (internet, mobile, cloud, AI), but human nature doesn’t.

• Companies and investors have institutional amnesia. The people making decisions in 2020 weren’t the ones who lived through 2001. Every 7-10 years, we get a new cohort that has to learn these lessons the hard way.

On Capital and Discipline

• Cheap money makes bad companies possible. When capital is expensive, only businesses with real unit economics survive. ZIRP didn’t just fund innovation; it funded a lot of nonsense.

• Financial discipline isn’t sexy, but it’s what separates companies that last from companies that flame out. Amazon and eBay survived the dot-com crash because they learned to be ruthless about costs.

On Hiring and Talent

• Overhiring in boom times creates painful corrections later. It’s better to be slightly understaffed and hungry than bloated and complacent.

• Salary inflation is a ratchet. It only goes one direction. Once you establish high comp bands, you can’t easily walk them back without losing people.

• The “hire fast, fire faster” mentality of 2020-2022 destroyed a lot of trust between employees and employers. That cultural damage will take years to repair. In fact, we are still repairing it in 2025!

On Valuations and Reality

• Revenue multiples are a lagging indicator of delusion. When investors start pricing companies at 20x revenue (or higher), they’ve stopped caring about fundamentals.

• Every bubble has a “this time is different” narrative. Dot-com had “eyeballs,” 2020 had “COVID acceleration,” 2024 has “AI transformation.” The narrative always sounds compelling until it doesn’t.

On AI Specifically

• AI might be transformative, but transformation takes time. The internet didn’t reshape business overnight. It took 15-20 years. Expecting AI to deliver 10x productivity gains in 2-3 years is naive.

• We’re confusing “making smart people more productive” with “replacing entire jobs.” Those are very different value propositions with very different P&L implications.

On Maturation

• Growing up as an industry means accepting trade-offs. You can’t have hypergrowth AND profitability AND work-life balance AND unlimited runway. Mature companies pick their battles.

• The shift from “move fast and break things” to “move deliberately and build things that last” isn’t a betrayal of tech culture, it’s evolution.

On Leadership

• The best leaders I’ve worked with treated bull markets with skepticism and bear markets as opportunities to build. The worst leaders did the opposite.

• If you can’t explain your business model to a smart 12-year-old, you probably don’t have one. Complexity is often a smoke screen for businesses that don’t make sense.

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Before we get into the scenarios, it’s worth exploring why most teams and their leaders don’t dig into this aspect of running businesses. I’m sure that most of you, after reading the opening paragraph, are thinking, “Yeah, this makes sense. Why isn’t anyone on my team actively figuring out how to speed up decision-making?” I don’t have a clear answer to that, but I have a few theories.

My first hypothesis is that the question of productivity, or lack thereof, pops up only during moments of stress. For example, a delayed project will invariably force the room to discuss, “How did we get here?”, “Are we having a problem with productivity?”, “Is the team working hard enough?”, and so on. When these problems are raised under stress, everyone is looking for a quick fix. It will take someone—usually someone with a broad enough purview, like an executive—to find all the stops the decision train has to make before it’s finalized and then figure out how to make the train go faster. Translation: it will take some time and effort to figure out how to find all the choke points and eliminate them. However, in the room, which is already charged with stressful questions, no one will present it as a fix because the fix will take time to implement. This is why teams default to some of the other choices when it comes to fixing projects, like cutting scope, moving people around, 996, etc. And when the time comes to do a retro on the project, decision-making velocity is very rarely mentioned because it feels like something that will take a long time to discover and optimize. However, that’s not true. Here are some common black holes, in no particular order, that will eat away at your productivity and how to fix them.

What to build - If you ask anyone their opinion on how a specific feature should work, I can guarantee you’ll get a million different opinions and a thousand conflicting ones. Heck, you’ll get conflicting points of view even if you ask your customers that question. In my experience, when teams attempt to take a democratic approach to determining how a specific feature should function and the nitty-gritty details of its various knobs, bells, and whistles, they unknowingly sacrifice a great deal of velocity.

People often mistakenly compare building features to building a house. You won’t build a house without the wholehearted approval of the future owners, right? Building software features is not like constructing a house, but rather like drawing on an Etch A Sketch. If you don’t like the drawing, you can change it. You can either spot-fix it or erase the whole damn thing and start over.

If you’re a product development leader trying to figure out what to build, I recommend having a strong point of view on what the feature should look like. You should base that point of view on your own research, customer feedback, and industry validation as applicable. You don’t need your team to approve the details as long as they’re good with the high-level approach. What you do need is a set of strong success KPIs. Extra brownie points if you can bake in experimentation to figure out which bits of the feature resonate with customers and which don’t. Your success KPIs should determine how to evolve the feature, not your team, your sister teams, or your boss. In fact, the correct place to lean on your team’s feedback is to discuss the KPIs and evolve both the feature and the KPIs that measure success AFTER it has been released.

Bosses, sorry to say that you’re some of the worst offenders. I’ve encountered countless scenarios in my career where executives try to put their thumb on the product roadmap or feature set because of their “gut” instinct. I’m sure most of your instincts are on point, but in the grand scheme of things, I recommend you let your team leaders make those decisions and optimize for speed rather than satisfying your ego. The only exception here is a founder who is trying to change the trajectory of the company.

In short, optimize for rolling the dice, measuring the results, and iterating, versus debating forever about how many sides the dice should have or its color.

What should it look like - Put a bunch of random people into a UX review and instantly they all become designers with a point of view on what the user experience should look like, including having opinions on very low-level details like what the color palette should be! I absolutely recommend against UX reviews that have non-designers in them. The only exception should be the product manager who is working closely with the designer to design the overall experience. And in the end, if the designer and the product manager agree on the overall user experience, there’s no need to include all other feedback. Everyone gets a voice, but not everyone gets a vote.

However, just like you can use success KPIs like engagement, stickiness, and activation to measure how well a feature is doing, you can use usability metrics like task success, time on task, number of errors, ease of use, and NPS scores to figure out how well the user experience is working out for the end user. Additionally, UX flaws will also affect feature-level success metrics like engagement and activation, so you can look at those as well to figure out how to evolve the user experience. Just like in the previous section, optimize for speed and measurement versus democracy and social cohesion. The user experiences of modern web and mobile applications are fairly easy to change, so don’t overthink what the initial experiences should look like. Just get it out there, measure, and iterate. And again, bosses, please don’t put your thumb on the UX design. Assuming you have a competent team, focus on giving them thoughtful feedback and let them decide what they want to do with it. One of the worst UX reviews I’ve ever been a part of was when they invited the CEO to it. They were hoping to show off their design, but instead ended up needing to rework many trivial parts of the user experience, which in the end didn’t amount to much.

System Design - Senior engineers enjoy organizing design reviews. Who doesn’t want to feel like a king (or queen), guiding their loyal subjects on how to live? Design reviews are beneficial, as long as they aren’t a gate. Many companies treat them as a gate, where the team proposing a new design MUST get approval from the design committee, typically made up of senior, staff, and principal engineers. While it’s extremely valuable to get feedback from the braintrust of your engineering organization, I have concerns about those meetings becoming a gate.

The right approach is to require all major design changes to go through a review, but allow the presenting team to decide whether to accept any or all of the feedback from the committee. Ultimately, the presenting team will have to live with the outcome of their decision, so it doesn’t make sense for them to oppose and commit to a decision that’s forced upon them by an ivory tower committee that won’t be present during a production incident. One exception is if your design not only impacts your systems but also affects systems owned by another team. In those cases, building consensus and alignment is necessary, and if that isn’t happening, the leaders of those organizations need to meet and agree on a way forward.

How to launch it - This is more of an issue with brand new, zero-to-one product/feature launches than incremental updates to existing features, but generally speaking, the quicksand teams fall into right before they’re about to launch something is the conundrum of, “Is it good enough?” Other variations of that question could be, “Did we fix all the bugs?” or “How can we be SURE that this is going to work?” and so on. Bottom line: even the best laid plans can implode after launch and, conversely, the worst laid plans can sometimes land really well with customers. There are numerous stories of side projects or features becoming popular enough that teams abandoned their main ideas and pursued the side idea instead. Slack is a great example. The team was originally working on an online game when they built Slack as an internal communication tool because what was available in the market didn’t work for them. And Slack became so popular with the team that Stewart decided to kill the online game idea and just focus on Slack full-time, and the rest is history. The bottom line is, you really don’t know exactly how a product or feature will do in the wild until you release that damn thing. No amount of testing, user research, or prayers can ever give you 100% confidence that it will work exactly how you predicted it would. My recommendation to product development teams is to always roll the dice as long as you can control the blast radius in case the dice roll out of your control and into a ditch. Meaning:

• Define and instrument metrics (customer and system) that will immediately tell you how the product is doing post-launch

• Release it to a small cohort of customers first. If your metrics are holding steady, expand the pool of customers who have access to it

• A/B test wherever you can

• There’s no rush to GA any feature. Slap a beta label on it and keep it there until you’ve seen enough customer usage in the wild to determine if the feature is working for your customers or not. Some teams rush to GA things because they committed something to leadership. Trust me, your bosses aren’t going to be upset that you’re not GAing it. They’ll be upset if you GA it and the feature gets punched in the face by your customers

• Don’t nitpick user experience warts. If the product/feature is solving a real pain point for customers, they’ll find a way to love it. Case in point: just download any banking app

• Don’t overthink GTM activities. Assuming you know your customers well, just put out a plan that you think is good and launch with it. If the feature is valuable, customers will find ways to find it and use it

• The only thing you SHOULD be somewhat sure about before launching a new product or feature is its pricing. Even with a beta label, it’s very hard to change pricing on customers without undergoing some (or a lot of) churn. So if you want to spend extra upfront time on anything, spend it on nailing your pricing

Before wrapping up, a quick note about escalations. One of the things teams and leaders struggle with is escalating quickly. Meaning, if there’s a disagreement, pushing the escalation upward to someone who can break a tie. Either consciously or subconsciously, people feel it’s poor form to escalate. They think it’s like crying wolf. In my experience, it’s the opposite. Senior leaders and executives desperately want to help. They want to speed things along. In the context of making decisions, never feel like you’re being a snitch by escalating things to your boss quickly. Escalate quickly and pull others in who can make the decision and help move things along.

The irony of optimizing for decision velocity is that it feels riskier in the moment but is actually far less risky over time. Yes, you’ll make some wrong calls. But you’ll learn from them quickly, course-correct, and still ship faster than teams that spent months trying to make the “perfect” decision. Speed compounds, and so does the learning that comes with it.

And that is it! Until next time!

Other variations of that same question might be: How do I build a brand? Do I need a brand? How do I start sharing my thoughts online? What if I come off like a cheap influencer?

We're going to unpack the following in this post: Should you invest time in creating an online presence? How to do it the right way? What are the benefits of doing it? And what are the realistic returns you can expect from your efforts?

But before we get into anything, let's start with the grand 'why?' Why do anything?

Why do it at all?

On its surface, sharing your thoughts and opinions online feels like a thing humanity created in the last fifteen years or so, but the reality is, humans have been doing it since they gained consciousness. The oldest hand paintings are over 64,000 years old, found in the Cave of Maltravieso in Spain. Recently, an even older hand stencil was discovered in caves in South Africa, which were purported to be over 150,000 years old.

As Tiago Forte says in his book, Building a Second Brain:

"Self-expression is a fundamental human need. Self-expression is as vital to our survival as food or shelter. We must be able to share the stories of our lives—from the small moments of what happened today at school to our grandest theories of what life is about."

If you have no interest in building any online presence, professional or otherwise, you still have to figure out how to express yourself. You can write. You can paint. You can teach. You can tell stories. You can build companies.

Bottom line: there's nothing inherently wrong with putting your thoughts out there in the world in some shape. Obviously, there are people who take it too far and get trapped in the empty validation cycles social media offers, but there's nothing wrong or immoral about sharing with the universe how you perceive it. As long as you don't care about likes or retweets.

So the first thing I want you to take away from this post is that you don't have to give a reason to anyone to start expressing yourself online or otherwise. If you feel like it, do it. Ignore all the haters and the noise. Humans are hardwired for self-expression. Don't fight it.

With that out of the way, let's dig into the top three things a robust online presence might lead to.

Realistic outcomes

Corporate career opportunities

The simple answer is 'No.' Yes, having a polished online presence full of well-thought-out posts is a tremendous addition to your overall profile, but in itself it won't bring you career opportunities or advancements.

For example, if you're fresh out of college and have a tremendous online presence because you break down complex topics into understandable bite-sized posts, that won't lead you to that coveted job at one of the FAANG companies. What will get you that career opportunity or advancement is:

1. You have a track record of excellence in the field. So if you're an engineer, you've built solutions that are used by millions of people. If you're a leader/executive, you've successfully built teams that have delivered tremendous value to the company and its customers. Online likes and comments aren't enough. You need real-world wins. If you're fresh out of college, build things. Build apps, build products, and try to find customers for them. Even if you fail, you learn something from it and, more importantly, you can put it on your resume.
   

2. You know the right people. If you're an individual contributor, you've successfully networked with the right hiring managers and are in their network. If you're an executive, you've built positive relationships with other executives, including CEOs and board members, who will help you land your next gig. Also, successful networking doesn't involve connecting on social and immediately asking them for help. Successful networking means you help out unconditionally. When you throw care and positivity into the world, it will make its way back to you.
   

And that's it. Get the right experience and network with the right people to find your next gig. To be clear, an online presence will help you stand out against other candidates, but in itself, it won't help. I've also seen well-respected tech executives with zero online presence. On the flip side, I've personally interviewed and rejected well-loved professional influencers for leadership roles because it was clear that execution was not their strength.

Building a community

Humans have been building communities since they figured out how to stand upright. Humans are fundamentally social creatures, and communities of like-minded people satisfy our need to belong. It isn't just about belonging. Sharing space with others with shared interests and worldview prevents us from feeling lonely as we navigate our professional and personal lives. We can ask for and get help and eventually become better versions of ourselves.

Sharing your worldview publicly is a great way to build a community. In fact, in the beginning, when I started writing on LinkedIn, my intention was never to use it as a lead generation mechanism. It was always about finding and building a like-minded community. At its core, all my writing, LinkedIn, Substack, and my book were, are, and will continue to be my way of finding and nurturing my tribe.

Building a business

If you've built a community, you can decide to monetize it if you choose to do so. It isn't 'icky' to sell products and services to your community. It's about knowing the value of your knowledge and charging the right price. Your time is valuable, and you should be paid for it.

It doesn't matter if you're the CEO of an established company or a solopreneur trying to find customers for your online business—having a thoughtful and targeted online presence will help you find customers faster. Over the course of the last six months, I've built up my executive coaching business to a respectable six-figure income stream, and my online presence and my book have contributed greatly to it. Even when GenAI has scaled beyond our wildest imaginations, people will continue to buy from other people.

Lastly, building a durable business takes time. The knowledge I sell took me over two decades to acquire. It took me about a decade to build my community. I've been writing on LinkedIn for that long! It took a few years to figure out what products/services to offer. It took a few months to nail down pricing. I'm sure there are ways to do this faster if you don't have a day job, but my meta point is that these things take time and require perseverance.

Before we move on to how to get started and do things the right way, I want to address the elephant in the room. I haven't mentioned influencers. Yes, influencers make a lot of money, but the way they make it doesn't pass my morality test. Take the Logan brothers, for example. They became famous on YouTube by posting sensational content and using their platform to sell crypto scams or energy drinks that cause heart attacks. No thanks. My basic rule of thumb is: sell something that's built on your knowledge and credibility.

How to put yourself out there (the right way)

How to start?

Sharing my thoughts online was never a deliberate action. In fact, I was terrified of doing it. What if the world doesn't like it? What if people make fun of me? If I was so worried about sharing the words, why did I do it? I did it because the words rattling in my head demanded release, and when blogging took off in the early 2010s, I decided to use that as a way to give the words in my head a way out into the world and spread their wings. I didn't know it back then, but I was allowing self-expression to bloom inside me. At some point in your life, your consciousness will tell you it needs a way to express itself. Don't fight it.

Getting back to how to start. Just start. No one is going to make fun of you. No one is going to dislike your posts/content/art. No one is going to ridicule it. In fact, you might be your own worst enemy by being very self-critical. The worst thing that could happen to you is that nobody cares, which is what happened to me when I started, and that's completely OK. It doesn't matter if your first public post is fifty words or five hundred words. Remember, the first step is to just start. The rest will come later. Just start.

What to create and share?

Most (if not all) of you readers are tech professionals, so I'm going to stick to talking about creating and sharing content about your respective professional journeys.

There are numerous social platforms that will allow you to get your word out. However, if you're a tech professional just looking to get going, I recommend LinkedIn. Why? Primarily because there's a high chance you are already familiar with it, and your future tribe is already on the platform.

OK, so you've picked LinkedIn. What do you share? If you Google "What should I share on LinkedIn?", it will spit out a million different frameworks. There are many useful ones out there, but my advice, if you're just getting started, is to ignore all of them and share what's on your mind. I'm not talking about sharing what you had for dinner or the walk you took during lunch, but about what tickled your intellectual curiosity that day.

Maybe it was an interesting conversation you had with a colleague that led to an interesting insight. Maybe it was your own insight you got after reading something online. Maybe it's just an after-work reflection on work life. The bar I set for myself for what to post is, if I share this with someone intellectually curious, will they be interested enough to have a discussion with me about it? Pick authenticity over polish. In the words of Rick Rubin, the goal is not to play and win, but to play and play.

Once you get comfortable sharing on LinkedIn, I recommend picking one more platform to extend your reach, like Substack or Medium, if you want to grow your community and monetize it. LinkedIn is great for short-form content and building a community, but it isn't great for monetizing them. Substack and Medium, on the other hand, are purpose-built for monetizing your community.

Persevere

If you don't have any intentions behind building an online presence besides just sharing your thoughts online as a form of expressing yourself, you can skip the rest of this post. Read on if you want to build a community and/or a business afterward.

The very first posts will be exhilarating. If you're an experienced professional, there's a real chance that your tribe will start showing itself by engaging with your content. That will motivate you further to create more content. More engagement. More motivation. More creating. This cycle will continue until you hit your first creative block, and boy, it will suck.

When I hit my first creative block, I just gave up for a bit until the creative juices started flowing again. However, you can't use that as a remedy forever. The blocks will last longer, and it will become harder and harder for you to start creating again. I've come to the conclusion that the remedy is to push through the dry spells. There are a few techniques that I use regularly to get through my writer's block:

• Switch up what I'm currently reading, listening to, or watching. If I was reading fiction, I switch to non-fiction and vice versa. This helps with jumpstarting my creativity.
  

• Commit to writing 'something' every week. Even if what I write is gibberish and not worth sharing, I still write it down. I've written about fifty essays on Substack, but there are fifty more in the graveyard section of my Google Doc. Heck, I even wrote a short story that's on Substack somewhere. As Stephen King says, 'If you want to become a good writer, write every day.'
  

• Give yourself a time-out from doom scrolling. Delete all social media from your phone and add web blocks on your laptops. What I've realized is that creative ideas that end up becoming my LinkedIn or Substack posts are not inside me. They're in fact outside me. All around me. To let them in, I need to make space for them inside me.
  

I didn't put 'ask AI for inspiration' on that list because it can't inspire you. It will regurgitate what's currently 'hot' on the platform. Inspiration is a uniquely human trait. Either you get inspired yourself because you experience something profound happening to you, or you become inspired by talking to another human.

After you successfully get through a few of your creative blocks, it will become a habit.

Selling

I'm not a sales expert, so I won't risk saying the wrong thing, but here's what I've learned from building my coaching business over the past six months. Creating thoughtful content on LinkedIn has provided tremendous social validation. When I reach out to a prospect in my network, my profile passes their sniff test before we even have a conversation.

However, if you're constantly pushing products and services in every post you create, you won't be successful. Audiences get tired very quickly of being sold to. I've seen well-intentioned professionals turn their LinkedIn feeds into infomercials, and their engagement drops off a cliff.

What surprised me most is that when you help people unconditionally through your content, they start reaching out to you. I get more inbound inquiries now than I ever did when I was actively trying to sell. People want to work with someone who clearly knows their stuff and isn't desperately chasing them down.

And coaching is just one product you can sell. There are also courses, newsletters, podcasts, etc, and many more products and services you can explore selling.

Get a coach

If you're serious about building an audience on social platforms, get a coach. All these platforms have unique quirks that a coach will instantly point out to you. For example, on LinkedIn, dropping a link in a post will cause the algorithm to throttle its engagement. Why? LinkedIn doesn't want its users to leave the platform. This is why experienced LinkedIn authors drop links in comments instead. I didn't know this until I talked to a coach.

If you're considering building an audience on LinkedIn, I highly recommend Natasha Walstra (https://www.linkedin.com/in/ndwalstra/). When I first met her, I had been writing for almost a decade on LinkedIn and considered myself somewhat of an expert, but within a few weeks of working with her, I realized how much I didn't know about the platform. To be clear, she didn't ask me to write this. I genuinely feel she's a great coach and deserves her flowers, that's all.

Summary

And that's it, folks. I hope this helps anyone looking to take their first steps in building an online presence. If you have additional thoughts or questions, please share them in the comments!

Here we go.

Hate the other person - I have seen mostly newer (and some experienced) managers fall into this trap. The trap being: you have to hate or strongly dislike the other person before you can deliver tough feedback to them. When you are delivering bad news to an employee or a peer, you don't have to be upset or angry or hateful. In fact, if you show up like that, the other person will immediately form an opinion that you just dislike them, and there is no way they can get on your good side.

In fact, I would argue that employees shouldn't have to worry about your good side and bad side. They should only worry about meeting the expectations set by you and the role they signed up for. You are not a dictator. If you overtly lean on having a good and bad side, you will only attract sycophants. You will be surrounded by yes people, which is wrong for many reasons.

Don't show up ready to show your bad side. Instead, show up with empathy, directness, and most importantly, facts. You don't have to use 'disappointed dad' language like, 'I am not upset, just disappointed' to get your message across. Be direct, be empathetic, use facts, and give them a way out. Don't just tell them they are not meeting expectations without also providing them a way to meet your expectations.

Relish it - I have met very few leaders who exhibit this especially nasty trait. These are leaders who relish or derive some perverse pleasure in putting employees through the wringer with the explicit goal of grinding them down to a point where they leave on their own, or their effectiveness drops to zero because they are living in constant fear. These leaders put employees on the spot, berate them in public (and call it radical candor), set traps for them, give them impossible tasks, and poison the well to a point where the employee cannot move to another team to escape them, and their only recourse is to leave.

This is absolutely the wrong way to manage people out. Leaders who use fear tactics to get people out were probably subjected to similar torture by their bosses, and instead of making the world a bit better by not repeating the sins of the past, they have decided to propagate nastiness.

Call me old-fashioned and sentimental, but I believe the universe keeps score. You will reap what you sow.

Be vindictive - This is when leaders make an employee's life miserable because they somehow 'wronged' them. Maybe they spoke up against them in public, or went to HR with a grievance, or went above them to their skip-level manager to complain about something. The right thing to do is to figure out why your employee is doing what they are doing.

Pushing back against you in public is mostly a good thing you want to encourage in everybody because it helps you validate your assumptions and prevents you from making a dumb decision. If your employee goes to HR or your boss to complain about you, it means they are afraid to come to you with their concerns. Maybe they don't feel safe or comfortable speaking to you, which in itself could be because of a myriad of reasons. Maybe you are a new manager and you both don't have a relationship. Maybe it's a personal matter they don't feel comfortable sharing with you.

Whatever might be the case, your immediate reaction to your employee not directly engaging with you can't be to make their lives miserable. The correct thing to do is to figure out why they don't feel comfortable engaging with you. Approach it from the standpoint of understanding them better so that you can help them better. Ask for feedback and act on it. In most of the cases I have encountered in my career, I was able to turn around a professional relationship by being self-critical, asking for feedback, and really acting on it.

Obviously, there will be situations where the employee is clearly trying to make you look bad or is making outrageous demands that cannot be met. Even when it becomes clear that it won't work out between the two of you, be empathetic, be direct, and use facts. Never be vindictive. Also, don't do it alone. Use your HR team.

Shit sandwich - This is something inexperienced managers do quite a bit. Heck, I did it when I was a newly minted manager and extremely afraid to deliver any tough feedback to any employee because of the potential disruption it might cause to the team's social cohesion and harmony. So a shit sandwich is when you deliver the bad news/critical feedback sandwiched between two pieces of good news. The recipients could be employees, stakeholders, bosses, and even customers. On its surface, it seems innocuous, right? The two pieces of good news soften the blow of the bad news. You delivered the bad news, and the recipient doesn't feel too bad about it. Win, win, right?

Wrong.

When you are delivering bad news, you don't want to bury the news or distract people from it. You are delivering the bad news because you want people to focus on it. You want people to zero in on it and act quickly, so that you can fix the damn problem! If you are delivering bad news to an employee, you want them to lean in to figure out how to fix the problem. If you are delivering bad news to stakeholders, you want them to understand the reality and what the next steps might be. The shit sandwich doesn't make the problem go away.

In fact, a shit sandwich never goes away. You know why? Nobody wants one.

Muddy the waters - This is a variation of the shit sandwich, but worse. This is when you hide the shit sandwich in its entirety and don't tell the other person any meaningful details. You give them half answers or poorly thought-through feedback filled with anecdotal opinions, and at the end of the conversation, the recipient is left scratching their head and wondering if they did something good, or something bad, or something else altogether.

Don't beat around the bush. If something is not working in a project, say so. If someone is not hitting their commitments, say that directly and support it with facts. If a project is delayed, say it is delayed and follow up with what you are doing to fix the ship. Be empathetic, but direct, and always provide a way out, especially if you are giving critical feedback to an employee.

Remember, the 'resource' you are dealing with is a real person with real lives, families, ambitions, and dreams. If you are going to make them question their dreams and ambitions, give them a way to succeed as well.

Surprise them - Lastly, don't surprise them. Our minds are wired for procrastination. Neuroscience research suggests that procrastination stems from a conflict between different parts of the brain, particularly the prefrontal cortex (responsible for rational thought and planning) and the limbic system (which prioritizes immediate gratification and emotional responses). This means that our brains are naturally drawn to the path of least resistance, even if that means delaying important tasks for short-term emotional relief.

Fight that urge, because if you don't, you will end up letting that problem (that requires you to deliver tough news) fester and become worse. Stakeholders, customers, employees, and bosses all want to hear about what's not working sooner rather than later.

P.S - I convinced a few brave leaders to let me workshop some ideas with them about navigating messy conversations. Apparently, it didn't go as badly as I thought - here's the feedback:

So, if you are looking to organize a workshop for your leaders around tough conversations, reach out at info@maheshguruswamy.com

Until next time!

For me, the pursuit of perfection guides my decisions. Jobs I take, books I read, people I talk to, people I coach, the friends I make, the relationships I nurture are all about becoming the best version of me. The perfect leader. I also know for a fact that I will never become this perfect leader. I don't think there is any leader, dead or alive, who has all these attributes and skills. But that doesn't deter me. I will pursue it forever until I am ashes to ashes and dust to dust, and that is good enough for me, because I know that pursuing this perfection will allow me to make an impact. It will let me make a small and memorable dent in the corner of my universe. I have always known what my definition of a perfect leader is, but surprisingly, I have never written it down. Well, here it is.

The Hype Trap

In my observation, the vast majority of tech leaders chase hype. They see something trending and want to signal to their investors and customers that they're at the bleeding edge of whatever is new, moving quickly to insert the trend into their product or marketing—often against the recommendations of their internal teams. We've all been in situations where bosses wanted to sell shovels in a gold rush, even when the team was saying there's no gold in those hills. Chasing hype never ends well and sometimes results in negative press and customer backlash. The NFT craze of 2021-22 is a perfect example. Companies tried to ride what they thought was a wave, only to realize it was a cliff. Every company (and entitled celebrity) that embraced it ended up at the bottom.

The best leaders do the opposite. They're comfortable telling investors and board members "no" when asked about the latest trend because they can see through hype to spot genuine innovation. They recognize and visualize what the future should actually look like. Andy Grove is a perfect example. When he led Intel, the company's core business was memory chips, but they faced intense pressure from Japanese competitors dumping memory chips at rock-bottom prices. The conventional path would have been to compete head-on—innovate on memory chips, cut prices, and sell more. But Grove knew the future wasn't in memory chips; it was in microprocessors. Back then, microprocessors represented a small but rapidly growing market segment. Grove saw the future clearly, went against conventional wisdom, and bet everything on microprocessors. The results were staggering: under his leadership, Intel's market cap grew 4,500%, from $4 billion to $197 billion.

The Multi-Product Paradox

Most companies struggle to become multi-product companies, even though it is a proven tactic to reduce risks and cultivate new channels of growth and revenue. It is common knowledge that the product adoption curve plateaus after 8-15 years. In other words, there is only so much revenue juice you can squeeze from a single product. Only 25% of public companies generate more than 20% of their revenue from outside of their core offerings (source: https://www.tidemarkcap.com/post/the-paths-to-multi-product). So why don't companies eagerly adopt a multi-product strategy? The answer is, it is freaking hard. It takes an enormous amount of conviction and financial discipline to keep investing in a secondary product line, knowing that you won't see any returns from it for multiple years. In the case of AWS, it was decades! For a company to have this level of conviction, it needs a special type of leader. Most leaders will flinch during a downturn and reallocate resources to their core product offering. Only the perfect leader will stay invested in alternate business lines even if their board members are yelling at them to change tactics.

His wedding invitation might not be innovative or unique, but Jeff Bezos's multi-product strategy and conviction are one for the history books. He launched Kindle during the 2008 downturn. When companies were shutting down, cutting costs, and refocusing on their core business, Jeff launched Kindle because he was convinced that there was an unmet need there. Along with launching Kindle, he didn't pull back on investment in AWS, which had been announced just two years prior. Lastly, he made some blockbuster acquisitions, including Zappos, which he acquired for a whopping $1.2 billion in 2009. All of these have paid off. Amazon has grown ~2,500% from approximately $25 billion in revenue in 2009 to $640 billion in 2024.

Master Capital Allocators

Here's a fun activity. Ask your CEO (or any senior leader), 'What do you do?' Most will mention leading teams, driving growth, or setting vision. But the leader who answers, 'I allocate capital to create maximum returns' truly understands their actual job. Everything else—the meetings, the strategy docs, the team building—is just tactics serving this one fundamental responsibility.

The best leaders not only deeply understand their core responsibilities as capital allocators but are excellent at it. They put deep emphasis on cash flow versus earnings. They keep costs down by tapping into cheaper global markets for talent. They aggressively buy back stock to signal to the market that the shares are underpriced and thus drive the overall share price up and keep the company's capitalization healthy. They decentralize decision-making but keep capital allocation central. They patiently wait for a good price on acquisitions. They don't rush into any financial decision. And lastly, they are painfully frugal.

Henry Singleton, the founder of Teledyne, Inc., is widely considered one of the best capital allocators in business. As an example, he used the overvalued Teledyne stock in the 1960s to aggressively pursue acquisition targets, and when the stock became undervalued in the 1970s, he aggressively purchased it back, ultimately retiring a whopping 90% of the company's stock, which ultimately drove up the per-share price. This required enormous conviction to buy aggressively when his own stock was beaten down while competitors were expanding. As a result of his shrewd financial acumen and operational focus, Teledyne stock achieved an 18% compounded annual return between 1966 and 1991—12x the S&P 500! Everyone mentions Jack Welch's name as someone who consistently beat the market, but he can't come near Henry Singleton's results. In the time Jack Welch was CEO, GE stock performed 2x the S&P 500. Still impressive, but nowhere close to what Henry Singleton was able to achieve.

Culture Conviction

The perfect leader is obsessively opinionated about culture—not the feel-good values plastered on conference room walls, but the actual behaviors that determine how work gets done. They understand that culture isn't what you say; it's what you tolerate. And they're willing to be almost ruthless in protecting it. The way these leaders embed culture into their organizations borders on the fanatical: it determines who gets hired, who gets fired, how decisions are made, and how employees are expected to behave with each other. To outsiders, it might look cult-like. To insiders, it's what makes the impossible possible.

A great example of culture driving everything a company does is Amazon. To be clear, I am not suggesting that it's a great culture. I'm just saying that it's a great example of a culture where it is extremely clear to employees what they should and should not do. Amazon didn't stumble upon this accidentally. They refined and re-refined their culture over many decades. They wrote down how employees should work and behave. They use it in recruiting, performance management, investment decisions, and everything else in between. Another key insight I learned during my time at Amazon is that their cultural values (leadership principles in Amazon parlance) are not a reflection of their entire company but rather a reflection of the key attributes and skills possessed by the early leaders at the company that brought it its initial success. Essentially, the leadership principles adopted by Amazon were basically the key traits of the early executive team that Jeff hired. They figured out what brought them success and doubled and tripled down on it. When ex-employees complain about the culture of Amazon, it is considered a feature and not a bug.

The ultimate test of cultural conviction comes when leaders must choose between popular opinion and their stated values. A lot of CEOs easily fall into the trap of virtue signaling. Take any social justice issue—Black Lives Matter, the Russia-Ukraine war, the Gaza conflict—and chances are, companies and CEOs are publicly supporting the most popular side to earn some cheap marketing wins. Make a token donation, change your company logo on LinkedIn, and boom, virtue signaling complete. It takes a special type of leader to go against the grain and take the heat for it.

A good example of this is Brian Armstrong, the CEO of Coinbase. At the peak of the Black Lives Matter movement in 2020, Brian sent his now-infamous "No Politics" memo. When every company was publicly supporting the racial justice movement, Brian went the other way. He told his employees that Coinbase would keep its focus on solving for its customers and wouldn't take any political stances. He also offered severances to employees who were uncomfortable with his "No Politics" memo. About 5% of Coinbase took the severance and quit, and that was okay with Brian. This example shows both the power and difficulty of cultural conviction. While Armstrong stood firm on his principle, his own inconsistencies—like posting political content shortly after his memo—highlighted how challenging it is to maintain perfect cultural alignment. In general, though, I think it's a good example of a leader standing up for what they believe in and dealing with the consequences without regrets.

Talent Obsession

This is somewhat connected to the previous section, but it's worth calling out that the best leaders are extremely opinionated about who gets hired and who has to go. They are willing to break the bank for the best talent and don't hesitate to cycle out people who are not good fits for the company.

A great example is Reed Hastings of Netflix, who spent months courting Patty McCord to become Netflix's Chief Talent Officer. She kept saying no, but Reed kept showing up at her office and inviting her out for coffee, bringing other Netflix executives along until she relented.

On the flip side, Reed Hastings is also the leader who went to extreme lengths to ensure Netflix has a low tolerance for poor performers. He implemented the 'Keeper Test,' where he would ask managers if they would fight to keep an employee from going to another company for a similar job and pay. If the answer was 'no,' the employee would be let go with generous severance. Steve Jobs also had a very direct approach—he would fire people on the spot for poor performance and sometimes even eliminate entire product lines if he thought they weren't performing up to his standards. Some readers might find these steps extreme, and to be sure, there is a real human cost to these tactics. But there is no question that Netflix and Apple have tremendously benefited from having a high bar for talent.

The Human Equation

For a leader to be able to do all the things I described above, they also need extraordinary personal skills. They need to be warm, welcoming, charming, forceful, and decisive simultaneously.

Think about it. Convincing a board to co-sign a risky multi-product strategy during a downturn requires both analytical rigor and the ability to inspire confidence. Firing someone while maintaining team morale demands both decisiveness and empathy. Rejecting popular trends while keeping investors engaged requires charm paired with unwavering conviction.

The best leaders master this paradox of being simultaneously supportive and demanding, patient and urgent, humble and confident. Without these interpersonal skills, all the strategic brilliance in the world becomes academic—because leadership, ultimately, is about getting exceptional results through people.

Conclusion

I started by saying I'll never achieve this perfect leader ideal, and that's precisely the point. The leaders I've described—Grove, Bezos, Singleton, Hastings—weren't perfect either. They made mistakes, had blind spots, and faced countless failures. But what made them exceptional was their relentless pursuit of these principles, even when it was uncomfortable, unpopular, or uncertain.

The beautiful irony is that by accepting you'll never be perfect, you free yourself to take the extreme actions that perfection demands. You can tell your board 'no' on the latest trend because you're not trying to look smart—you're trying to be right. You can fire underperformers because you're not trying to be liked—you're trying to build something lasting.

So pick one (or two) of these areas and start obsessing over it. Become unreasonably focused on capital allocation, or culture, or talent. Make it your thing. Because in the end, the leaders who change the world aren't the ones who do everything well—they're the ones who do a few critical things extraordinarily well, and have the conviction to keep doing them when everyone else thinks they're crazy.

Until next time!

Starting to sound like a grim prospect, right? I personally don't think most people are living at the edge of chaos, where one bad conversation might cause them to spiral out. However, I have noticed that in the current socio-political-economic climate, leaders are facing rapidly rising pressures. The pressure comes from all sides and is often relentless. Investors want growth and profitability. Customers want high-quality features at low costs. Competitors try to undercut your every move. Employees want autonomy and stability. I talk to a fair number of C-level executives, and every single one of them is stressed out. They are all trying to balance a multi-variable equation that cannot be balanced without pissing off at least one variable. It's great to be at the top when things are humming along. It is absolutely terrible when things are going poorly. When things go south, everyone wants a piece of the person at the top. In fact, I am fairly certain that before this period of uncertainty is over, at least a few executives I personally know will pull the ripcord and bail out of the profession.

So what can leaders do? A common piece of advice given out (including to me) is to compartmentalize. Board member yelled at you? Compartmentalize it. CEO yelled at you? Put it in a box. Customers yelled at you? Get a bigger box. Employees yelling at you? Get a box for the box. Put it in the box and hide it away.

What is compartmentalization and why is it considered a skill for leaders? Compartmentalization at its core is a form of mild dissociation. It's separating the unpleasant parts of your psyche that are in conflict with each other and creating a mental divider between the two conflicting thoughts to avoid cognitive dissonance. For example, a high-flying salesperson who just sold software to an authoritarian government and scored a six-figure bonus might put their work life in a box and hide it away so that they can continue to live a normal suburban life, go to PTA meetings, host neighborhood barbecues, etc. In this case, "hide it away" means I am not going to think or talk about it outside of work. I am not going to discuss the ethical or moral implications of what I do. After I am done with work, I am just going to focus on being an awesome parent and a productive, happy member of my little corner of the world.

When I first brought this topic up with my then-mentor ten years ago, they gave me the exact same advice. I had just been yelled at by my boss, my boss's boss, and one of my employees on the same day, and I was pretty much close to throwing in the towel that day, so I was really looking forward to talking to my mentor. About ten minutes into the conversation, they said, "Mahesh, what you have to do is compartmentalize these things. You can't let these get under your skin." For the next few years, that's what I did. I tried to gently dissociate from the negative parts of my work life. Every bad day at work went into a box, and the box went under the metaphorical bed beneath my amygdala.

So I did this for about five years, and life was great.

PSYCH!!

It wasn't. It was terrible.

The box under the bed became bigger every year and eventually started spilling out. If my family wasn't there to ground me, the box would have exploded magnificently, and emotionally charged shrapnel would have flown everywhere. However, the stress got to a point where I started seeing physical changes in my body. I won't go into too much detail, but it involved lots of doctors trying to figure out what was wrong with me. They ultimately decided that something in my body was causing an inflammatory reaction, which was causing the physical changes I was noticing. That "something" was the leaky box under the bed.

It isn't healthy to bottle things up. It is a terrible idea to put things in a box and file them away. The only way to get through life without losing your mind (or body) is to process the shit that's inside the box. So what does it mean to process it? There are many healthy ways to process radioactive emotions. These are my favorites:

Find a friend (or two) - Leadership is often (always?) a lonely endeavor. Find someone to talk shop with. Bonus points if you can find someone who is in the same boat as you. I have a few close friends (my family being one of them) that I share everything with. As I have mentioned in a previous post, a little bit of commiserating is healthy as long as at some point both of you start moving into solution mode. There is nothing better than being able to unload to a friend who will instantly know what you are talking about and is there to hear you out and help you because you will do the same for them.

Journal/Write - I process things by writing them down. All my essays, including the book I wrote, are all about me trying to process the ups and downs of my professional world and trying to make sense of it all. The great thing about journaling is that the act of writing forces your brain to process what you are feeling. Difficult things will always appear simpler when you write them down. Trust me, it's like a cheat code for processing tough situations.

Meditate - I have written about the virtues of meditation in previous posts, but I will quickly recap. Meditation allows your brain to take a pause. When the engine overheats, you have to give it a minute to cool down; otherwise, it will start breaking down. Meditation doesn't have to be complicated or time-consuming. All you need is five minutes every day. Here are the steps:

• Find a quiet part of your house. Preferably a room with a door and a window.

• Place a chair next to the window and sit down on it. Back straight. Palms down on your knees. Relaxed shoulders.

• Remove all distractions. Remove your smartwatch and put it away. Set a timer for five minutes.

• Straighten your back and close your eyes.

• With your eyes closed, try to identify sounds you hear outside your window. Try to find birds chirping. Cars. Kids playing. Try to keep your focus on the sounds.

• In about a minute or so, your mind will calm down enough for you to go to the next step, which is counting down.

• Start with ten and count down to one. If a stray work thought pops into your head, don't get mad. Ignore it and continue counting down.

• Once you get to one, start counting down again, until your timer rings.

In the beginning, it will feel like your mind is racing all over the place, but with practice, you can get your mind to dissociate enough to recover from the pressures of life. Over time, you can increase the time to ten, fifteen minutes, or longer.

Physical fitness - Specifically, I am talking about strenuous cardio workouts. Not only are they good for staying healthy, but they're the only activity that causes your brain to release endorphins. Endorphins are natural painkillers that alleviate pain and elevate your mood. Find time to work up a sweat regularly, and it will result in lifelong benefits.

Make a change - Here is an interesting observation I have made over the years. People are more willing to stay in a crappy work situation than to take the risk of making a change for the better. It might seem like the risk associated with finding a new job or leaving your stable (but stressful) job to start a new company or business is way too high. Trust me when I say that silently suffering in a job is not worth it. If you are dreaming of starting a new company or business or finding another job because your current one is getting on your last nerve, do it. Do it now. The short-term effort might be high, but it is an effort you can control. Index on your happiness.

Seek professional help - Sometimes the stress and emotional weight we carry is too much to process on our own, even with friends, family, and healthy habits. There's no shame in recognizing when you need professional support. A therapist or counselor can provide tools and perspectives that friends and family simply can't offer. Executive coaches (ahem, like yours truly) can also be invaluable for leaders dealing with workplace-specific challenges.

In closing, I want all of you to remember one thing. The human condition is a messy one. We are all trying to make the best of this one life. Let’s remember that we are all humans and give ourselves some grace. God knows we need it.

So when I heard that question for the first time, I asked him to clarify what he meant. He replied, ‘Ok, so you execute and deliver this project. What happens next? Why does this work matter? How does this help customers? So what if you do this project? And if you don’t do this project, what happens? How does this affect the business?’ Then, just like that, it all clicked in. I had focused solely on the details of the project, how to design it, staff it, and execute it, but not so much on the impact the project could have on the end customers. The ‘So What?’ question was designed to get me to think critically about the actual implications of doing (or not) the project.

I have used this technique throughout my leadership and executive career. Asking myself the ‘So What?’ to all major investment ideas, thinking critically, and digging into the details of what will be the actual impact on the bottom line has helped me separate the chaff from the wheat. I also encourage my teams to think critically about their proposals, including clearly describing and quantifying the impact before submitting them to me, because they know I will ask the ‘So What?’ question, although I may not use those exact words.

Interestingly, I have found myself using this technique more frequently to cut through the hype and frenzy surrounding AI. In this post, I am going to take a few hype statements and try to cut through the chaff by using the ‘So What?’ technique.

Hype

Google’s Veo model can now create realistic movies from text prompts!!

Reality

Will it replace human filmmakers? Nope. Models are trained from data created by humans. Data pulled out of art, movies, and films made by humans. But here is the thing, though. AI models always narrow down to the commonalities in the dataset they are trained on. They are great at picking the most commonly accepted answer to a question. Essentially, it propagates the ‘sameness’ in the dataset. Unless you want to watch AI-generated movies that have extremely predictable visuals and stories, this will never replace real-world filmmakers. Will AI make it easier for filmmakers to make movies? Absolutely. It will take away the grunt work. However, creativity will need to be provided by humans.

Hype

Co-Pilot/Claude is getting crazy good at writing code from text prompts

Reality

Most software systems used by companies are deterministic in nature. AI systems (including GPT-based ones) inherently are not. Simply put, a calculator app should always output 4 when asked to calculate 2+2. Someone has to be able to course correct the AI-based coding system if it starts hallucinating, which it will. There will always be a need for a trained human to oversee what the AI system is doing.

Another fact is that sometimes the requirements are just wrong. The product manager might be thinking about the feature incorrectly, or could have misinterpreted the customer feedback, or the customer feedback itself may be incorrect. It will take a human to figure out if the thing the team is building is actually the right thing. Again, someone has to be at the wheel.

Lastly, the notion that AI will eliminate the need for mid-level engineers is simply incorrect. Senior engineers are promoted from mid-level engineers, who in turn are promoted from entry-level engineers. Maybe in the distant future, the overall size of the organizations will become smaller, but software engineering as a discipline isn’t going anywhere.

Hype

AI will replace customer support reps

Reality

Firstly, AI will not replace customer support representatives. Klarna replaced about 700 customer support reps with AI-based chat/voice systems, and it failed. Klarna’s CEO admitted that the automated systems were providing a low-quality service to customers. Now they are looking to hire real people back.

Getting answers to your questions is only one of the reasons people reach out to customer support. The major reason people continue to press 0 or yell, ‘I want to talk to an agent,’ to automated systems since the early 2000s is that humans understand other humans. A human can understand nuance and undertone. A human will break the rules to make their customer happy. They can lend a sympathetic ear. They can provide workarounds. Will AI reduce the overall size of CS teams? Absolutely. Will it replace humans? Not until AI develops consciousness.

Hype

AI tools will remove the need for branding and creative teams

Reality

Think about the most iconic brands in history. They stand out. AI tools that are built on top of existing data can never stand out. They propagate the sameness. If you let an AI tool design your brand, colors, and copy, it will be more of what already exists. Your brand will never stand out. The creativity that makes brands pop and copy come alive needs to come from a human. You think ChatGPT could have come up with the Nike swoosh or Apple’s Think Different tag line? I don’t think so.

Hype

ChatGPT can write sales emails as well as humans

Reality

AI-generated sales emails will end up in the same place you send all the human-generated ones. The current conversion rates on outbound emails are ~2%, and AI-generated sales emails will probably have a lower conversion rate.

Every time I apply my ‘So What?’ technique to all these hype moments, it becomes clear that most of the noise out there is just hype. And the people generating the hype are the ones who will most profit from it. A.K.A., the investors, founders, and companies who are heavily invested in this hype.

To be clear, the current crop of AI tools is not to be scoffed at. Their capabilities are phenomenal. They are great at filling in the blanks. They excel at automating manual labor or repetitive tasks. They will most certainly reduce the size of certain teams pretty significantly. However, they won’t build the next iconic brand. They won’t build the next iconic product. They won’t write the next bestseller. They won’t invent the next wave of software development technologies. To do those exceptional things, you need creativity, randomness, and a touch of chaos that can only be provided by humans. So next time you see a hype article on social media, ask yourself, ‘So What?’

People management as an established discipline has been around since the late 19th and early 20th century. It gained prominence during the peak of the Industrial Revolution, when companies needed to devise methods for organizing and motivating large groups of people to achieve maximum productivity. By all measures, this field should have become a well-established one. Something you can learn in school. A science. But it hardly is. In fact, it is nowhere close to it. This is because people management involves managing people, and people are ever-evolving.

Every generation that enters the workforce brings its own unique demands to the table, and when enough of the workforce is shaped in a specific way demographically, companies have no choice but to give up their old ways and adapt to the next generation, causing a shift in management philosophy. Because it is such an ever-evolving discipline, schools can’t really teach this. 2+2 might not be 4 if the first 2 are millennials and the next two are Gen Z employees. Thankfully, there are many independent thought leaders (ahem, me), people leaders, academics, etc, who fill this gap by writing extensively about this topic. Large technology companies often have extensive training programs they run for new managers.

I myself have written extensively about how to ‘do management’ the right way, but I have never written about the ‘don’ts’. Specifically, there is a set of unwritten dark patterns in management that you will most likely never learn from a book, your manager, or your new manager orientation at your company. Most likely, you will find out that what you did was a dark pattern AFTER you have committed the said dark pattern. This post is a deep dive into the ‘don’ts’. Let’s dive into some of the most egregious ones!

Snoopervising - This is when a manager tries to indirectly supervise somebody else’s employee. This typically pops up in large cross-functional teams, where an employee may report to a manager and also have additional deliverables that are managed by another manager overseeing the project the employee is working on. It might be easier for the manager/project leader to directly give tasks and direction to the employee instead of the employee’s direct manager, who might not have all the context of the project or might not even be attached to the project. It starts out with just task assignments, and sometimes it will veer into career conversations, promotions, salary increases, and everything else that really should be between the employee and their direct manager.

If you are a manager dealing with a cross-functional employee, it is completely OK to directly work with the employee on project-related tasks, but keep the employee’s direct manager in the loop at all times. And I mean at ALL TIMES. Also, regularly check in with the direct manager to ensure you are not crossing any boundaries.

However, it is completely unacceptable to direct them in personal or career development-related topics like career growth, salary negotiations, promotions, etc. For example, it's not ok to say stuff like, “You should ask for a 10% raise” directly to an employee who doesn’t report to you. It is okay to give advice, but don’t promise them anything. If you do offer any career advice, make sure to inform their direct manager as well, and make it clear to them that your POV is just advice and they should have that conversation with their direct manager. I have seen numerous instances where a manager tries to promise something to an employee who doesn’t report to them without consulting their direct manager, and it almost always ends in disaster.

Why is it bad to discuss all this directly? Because you don’t have all the context. You don’t know what their salary history is. You don’t know what their prior performance ratings were. You don’t know about the prior conversations they have had with their direct manager or HR. Imagine the heartache everybody has to experience if you offer a job to them on your team, only to find out they are in the midst of a performance improvement plan. Similarly, imagine if you push the employee to ask for a raise, not knowing that they got a huge bump the previous year. There are multiple quicksand pits waiting to suck everyone in if you are not careful. Bottom line is, push the employee to have these conversations with their direct manager, and if their direct manager isn’t being helpful, ask them to reach out to HR.

Pulling a Shaggy - This is when you privately blame your boss for a business decision you had previously disagreed and committed to. When you don’t own a tough message that needs to be passed down to your team and instead say, ‘It wasn’t me’, or, ‘my boss made me do it’, it is sending a strong message to your team that you don’t have any say in the future of the team and the team is basically puppet mastered by someone above.

Your team will most likely sympathize with you privately, but the overall engagement of the team will drop. Bottom line is, if you have decided to disagree and commit, commit fully. Yes, your team will most likely dislike you in the short term, but as long as you believe in the long-term decision-making capabilities of your leadership team, you will be OK. And more importantly, it will allow you to preserve your future autonomy. If you keep pulling a Shaggy, your team and eventually your boss will lose trust in you.

Backstab - There are many ways manager backstab their peers in the workplace. Let’s dig into the most common ones.

Abuse Confirmation Bias - Some managers use confirmation bias to build a relationship with their boss or peers. I.e, they will agree to every stance the other person takes, even if some of them are wrong and paint certain leaders or teams in a negative light. A lot of people do this unintentionally because talking trash about someone together is an easy way to build a relationship. However, remember that commiserating without discussing solutions can only lead to toxic relationships. At some point, the other person will realize, ‘All I do is complain when I talk to this manager.’

It is also very possible that the person you are trash-talking about also finds out about it and confronts you about it. This doesn’t mean you don’t discuss uncomfortable things, but my rule of thumbs are:

If I have critical feedback about a team, I start by sharing that feedback with the leader of that team.

If I have critical feedback about an individual contributor, I start with their direct manager.

If I have critical feedback about a leader, I start by directly giving them feedback, and if I don’t see any change, then I go to their direct manager.

Bottom line is, if you decide to give tough feedback, do it right. Don’t try to play Game of Thrones by whispering in people’s ears. You are not Varys.

Trash Talk - Managers often feel there is a pecking order. They feel their bosses have favorites. It is somewhat true. Some managers try to get on the favorite list by throwing shade on their peers in front of their boss. However, keep in mind that leaders become favorites with their bosses because they do two things well: 1) They have a generally good attitude about things, and 2) They get stuff done.

Also, people fall in and out of the favorite list all the time. So you don’t have to throw shade on someone and try to force them off the favorites list. All you have to do is deliver wins for your bosses/company, and you will automatically get into the favorites list and be given additional responsibilities. The best bosses, however, don’t have any favorites; instead, they treat every leader/individual separately and customize their interactions with them. But the bottom line is, you don’t have to step on someone to climb the ladder. Just deliver value, and you will automatically move up.

Turncoats - Some managers try to build relationships by taking sides. In private conversations, they might say things like, ‘I will support you when you bring this up publicly’ because they think that they are backing a leader whose idea will win, and they can ride the coattails of the winning leader to their next promotion. The problem is, not all ideas are winning ideas. Sometimes they get shot down. Not all leaders are great, either.

In general, I recommend taking the approach of not taking sides with a person, but forming a stance after thoroughly considering the surrounding facts. And if the facts prove you wrong, it is OK to change your mind because you are not anchored on a person but the idea the person is presenting. However, when you change your mind, you have to feel comfortable admitting that in public and explaining your reasons. The one exception to this is disagree and commit moments. If the group decides to go in a direction you are not aligned with and you have already said your piece, get ready to stop complaining about it and commit to supporting the execution of that idea or strategy.

Paint over failures - A common leadership flaw that I have observed in many leaders, including some very famous ones: A strong desire to appear infallible. They try to paint over failures or twist debacles as successes, or if everything fails, blame someone else for the failure. Never forget that you are holding it the wrong way. If you didn’t get the reference, just Google it :)

Always remember that your team will mimic your energy. By giving yourself permission to talk about failures publicly and learning from them, you are giving your team permission to do the same. If you try to hide or paint over failures, your team will do the same. In the long run, this will create a culture of being risk-averse, which will slow down innovation. In the worst case, it will prompt people to openly deflect blame onto others because they don’t feel comfortable taking responsibility for their failures.

It is somewhat true that publicly discussing failures will bring down the overall morale of the team. It is also true that some members of your team might question your judgment. However, an organization and a leader who can embrace failures in the right way will create a team that can innovate faster because they are comfortable with risks and are constantly learning from their mistakes.

Walled Garden - I am sure you all have encountered these teams. The manager tightly controls all information that goes in and out. The team members are extremely comfortable in their roles and are hesitant to say anything critical about their team. There are strict protocols to engage with the team. The deliverables are carefully crafted. Nobody really knows what their roadmap looks like. Basically, everything about the team screams, ‘We are closed to change, and we don’t accept feedback, and we won’t collaborate’.

A dead giveaway of a walled garden is when the team manager consistently refuses external help, even when they clearly need it to deliver on their commitments. Sometimes it might make sense to refuse help because the onboarding cost might be unacceptable, but if a manager consistently refuses external help, it means they are trying to prevent anyone external from spotting the skeletons inside the team.

My hypothesis about why managers go through the effort of creating walled gardens is that they want a level of control. They believe that by creating a team inside a fortress, they can ensure consistent growth and opportunities for themselves. At best, they will create stagnation, and at worst, they risk being let go by a boss who gets tired of their closed nature.

Every manager should want the best for their team and themselves. It is completely OK to ensure every member of your team (including yourself) has plenty of growth opportunities that will lead to promotions and pay raises. But walled gardens are not the way to do it. The right way to do it is to constantly assess if the problem your team is focused on solving is worth it for the company. Invite other leaders into the conversation. Ask for feedback on your goals, operating procedures, etc. And if it ever seems like your team is focusing on the wrong problem or is taking the wrong approach to solving it, be open to change. Pro-tip: Bigger and better opportunities will always present themselves when you are constantly focused on automating your way out of a job.

Avoid adopting any of these dark management patterns, and you will grow into phenomenal leaders. Until next time!

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If you don’t think through the repercussions of your big mouth…I mean choices—you could decimate the trust your organization, your boss, and your team have in you. This post is about how to be transparent the right way and the potential pitfalls of doing it wrong. But before anything, it is worth starting with the golden law.

If someone explicitly tells you not to share something, don’t share it. If you are one of those folks whose head will explode if you don’t share secrets, share it with your spouse or a close friend to get it out of your system.

Ok, with that out of the way, let’s first start with the laws of transparency

General laws of transparency (as defined by yours truly)

1. If someone explicitly tells you to not share something, don’t share it (Golden Law)

2. People managers are generally more discreet than others and will honor your request to keep things discreet.

3. Information travels the fastest in large organizations (specifically, sales and engineering), so be careful.

4. Sometimes, sharing information with people who might not normally have it could be mutually advantageous.

5. If you don’t know why you want to overshare with someone, just don’t.

6. Don’t gossip.

With those tenets in mind, let’s unpack what it means to be transparent with people. However, before you share something with someone, you have to consider two things. 1) Ripple effects of sharing something (sensitive or otherwise) with them, and 2) Why are you sharing it with them? Let’s unpack both.

To understand the side effects of sharing information with someone, consider the following-

How close are you to this person? Do you know where you stand with them?

Open up your company’s org chart and think through the implications of this person potentially sharing this information with their peers or maybe even their boss. As I mention in the laws of transparency, the larger the org, the wider the blast radius.

Can the information you shared with them affect their current roadmaps or plans? If it does, how do you think this leader will react, especially if the impact on their plans is negative?

Can your information negatively affect the career of somebody who is close to this person?

In all the above situations, what happens if it gets out that you are the source of the information? How does it affect your reputation?

Keeping all the above in mind, there are a few reasons you might want to share sensitive information with someone

You want their feedback about something sensitive and/or personal. When you ask someone to opine on something that is delicate or personal in nature, chances are they will keep it discreet. Also, this is a human flaw, but it boosts people’s egos when others come to them for feedback, and they would want to do the right thing, which is keeping the conversation private.

You want them to trust you with sensitive information. The easiest way to get someone to trust you wholly is to show them that you trust them by sharing information they might not have. However, before you do that, walk through the checklist from the top section to understand the implications of them getting access to this information. An easy way to build an information pipeline with someone is to share something personal that you don’t normally share with everyone. Because it is your personal information, the worst case that could happen is for someone else to ask you about it when you are not prepared. When others see you being vulnerable, they will be (or at least try to be) vulnerable with you.

I understand that not everyone will be comfortable about sharing personal information with anyone, but remember that there is a wide spectrum when it comes to personal information. The bottom line is that sharing something personal will enable that person to start trusting you easily. Keep in mind that this technique will only work as a way to kickstart (ha! a pun!) a relationship. To make it durable, you will have to do the hard work involved in building strong relationships, which is best saved for a future post.

You want them to actively or passively start thinking about something. I often share information with leaders (and individuals) if it helps them better prepare for the future state of their world. If the information is supposed to be kept discreet, I tell them so. If I want them to start thinking about it actively, I tell them that so they are aware of any looming timelines. If you don’t want them to do anything with the information you give them, then that information is just gossip. Gossip is the crack of the information world. Addictive, but not good for you or them.

If you are sharing critical feedback about a person, the only three people you can share it with are a) the person themselves, b) their manager, and c) HR, and preferably in that order.

Commiserating. OK, this last one is a little tricky and controversial. A very small amount of commiserating with a peer is sometimes helpful. Sometimes, it is helpful to share your miseries with someone else who either might be in the same boat as you or is in a position to understand you. However, for this to work, commiseration has to lead to solutions or collective brainstorming about how to get out of the hole both of you are in. It will feel good to dwell in the misery, but trust me, it won’t be helpful in the long run. Use the shared pain to build a path out of the pain. Staying in the pain is just like gossiping. Addictive but ultimately not healthy or helpful.

That’s it, folks, until next time!

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Leadership Coaching - If you are an engineering or product leader and want to learn how to make high velocity decisions under pressure, shoot me a note at info@maheshguruswamy.com. I am limiting the number of coaching clients I take on, so don’t wait :)

Book - If you are struggling with how to navigate messy leadership conversations and haven’t picked up my book https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN …tsk tsk tsk. Just kidding, please buy my book :)

If you are looking for a framework to make business decisions swiftly, read on!

Before we jump into the framework, there are a few high-level concepts that managers need to understand. The next section will provide a primer on the foundational building blocks of the framework. If you prefer to skip ahead directly to the framework, scroll down until you see a chart.

Foundational Concepts

Understand your role - If you are a people leader, how would you define your role? Why do you think the company hired or promoted you into that position? Is it to help your team achieve its goals?, Is it to help the individuals on your team hit their career goals? Is it to help manage the team’s stakeholders better? Is it to help the team’s customers? This list can go on for twenty more pages, and all of them will be true to various degrees. However, the cold reality is-

Your job as a people leader is to generate a positive return on investment on the money the company has entrusted you with.

And the longer you go without generating a return for the company, the higher the chances of you getting replaced. If the company isn’t doing that well, your runway to show a positive return becomes even shorter.

I know this is an extremely capitalistic way of looking at the world, but like it or not, that is the truth for most tech companies, especially VC-backed or public ones.

The weight of decisions - The definition of the word 'decision’ seems straightforward, right? Dictionary.com defines it as

“to make a final choice or judgment about.”

However, for leaders, I suggest using this definition: “Is this a risk I should underwrite?”

Every decision a manager makes carries some level of risk. By making a decision, you are inherently underwriting that risk. Even small choices, such as allowing the timeline to slip on a minor project, pushing a promotion through despite having doubts, or letting someone go, all involve some degree of risk. The more you understand the risks and their short- and long-term implications for your business, the better you will become at assessing them.

Understand the business - Leaders often make the mistake of staying in their lanes. While focusing is essential, to improve your decision-making skills and do so swiftly, you must understand how the larger company you work for operates. This is especially crucial in large organizations where individual teams can become so detached from the bigger picture that they lose sight of how they fit into the company's overall structure. As a leader, you must understand the following:

1. Who are your company’s customers?

2. What are your company’s acquisition channels? To phrase it in slightly less corporate language: How does your company find new customers?

3. Why do those customers prefer your company’s product over others?

4. Who are the competitors?

5. How is the company performing financially?

6. How does your team contribute to selling the company's products or services?

7. If your team ceased to exist tomorrow, what would happen?

Every company I worked for holds regular all-team meetings where the senior leaders present information about some combination of the bullet points I highlighted above. An easy way to get detailed information about the inner workings of the company is to talk to the leaders who regularly present at all-team meetings after those meetings. If you can’t connect with the presenter, try connecting with somebody who is one level down from the presenter.

Pro-tip: The team most proficient in the inner workings of any company is not the product, engineering, marketing, or sales teams; it is, in fact, the finance department.

The finance function consistently tracks every dollar coming in and going out and continuously assesses how each department contributes to the company's success and failure. That’s why a member of the finance team is always present as a speaker at all-company meetings. Build connections in that department to gain insights into your company's inner workings. By doing this research, you can quickly determine how a team-level decision you make will impact the overall company.

Understand your neighbors. Take time to learn about the cross-functional partners you work with. Understand what their roadmaps look like, what their goals are, and what keeps their leaders awake at night. Set up regular one-on-ones with the leaders and key members of your cross-functional partners. Chances are, any critical decision you make will affect them as well. The deeper your understanding of how they function, the easier it will be for you to grasp the ramifications of your decisions.

Understand one-way and two-way doors - I have discussed one-way and two-way doors extensively in my Substack writing and my book, but here is a quick primer for all the new readers. One-way doors are decisions that are very costly to reverse. Decisions like -

1. A pricing or packaging change

2. An acquisition

3. Creating a new line of business (products, services, etc.)

4. Creating a nontrivial footprint (people and products) in a new geographical location

5. Changing the name of the company

6. Changing the company values

7. Changing the company’s financial footprint/ownership dramatically (IPO, sale, SPAC, etc.)

8. Altering the infrastructure footprint dramatically, for example, going to bare metal from AWS/GCP or vice versa

9. Dramatically altering roles (e.g., removing certain job families) or compensation structures

10. Embarking on a new product/feature that is going to take more than twelve months and a full team (more than ten or so engineers, more than one product manager, and more than one designer)

The opposite of one-way doors is two-way doors, which are fairly easy to walk back out of. Decisions like... well, everything else not on the list above.

A common mistake new managers make is sitting on a two-way decision, thinking it’s a one-way decision. Pro-tip: Most decisions that leaders, including executives, have to contend with are two-way in nature. The key is to quickly recognize what is a one-way door and what isn’t. If it’s a two-way door decision, leave it up to the team to decide what to do. Provide your input during the discussion, but don’t bother tipping the scales unless you are dealing with extraordinary situations, such as an escalation, system outage, or basically any situation where you already know the ramifications of the team choosing the wrong option.

Build or find a core group - Every leader should have access to a core group of people who can provide quick feedback on their decisions. This core group could consist of peer leaders or senior individual contributors, preferably working in the same company. To be clear, I am not referring to a large group here. The key is for it to be more than one and fewer than five. It needs to be more than one because you want multiple points of view, and it should be fewer than five because anything more will make it harder for you to sift through the noise. It is also important to ensure that this group doesn’t merely echo your opinions. You want your core group to provide unbiased feedback, and you also want them to challenge you when necessary. You want your group to feel comfortable telling you when you are wrong, and you should feel comfortable receiving that feedback.

Put in the time - Nobody comes out of the womb learning how to make perfect decisions all the way. You have to put in the time. The more time you spend making decisions and learning from the outcomes (good or bad), the better and faster you will become in making high-stakes decisions.

Now that you know the foundational building blocks, here is a simple framework to use when making critical decisions.

High-velocity decision-making framework

If anyone has additional questions or feedback about the framework, feel free to drop them in the comments!

That is it, for now, folks! Until next time!

Leadership Coaching - If you are an engineering or product leader and want to learn how to make high velocity decisions under pressure, shoot me a note at info@maheshguruswamy.com. I am limiting the number of coaching clients I take on, so don’t wait :)

Book - If you are struggling with how to navigate messy leadership conversations and haven’t picked up my book https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN …tsk tsk tsk. Just kidding, please buy my book :)

However, in almost every company I have worked for, when executives make hard changes, their employees often look at them with a healthy level of skepticism. Employees frequently believe that the changes made by executives are not beneficial for the long-term health of the company or are short-sighted in nature, and executives become frustrated with employees for not understanding their rationale for the tough changes. Essentially, both sides retreat to their corners, viewing each other with deep distrust. It doesn’t have to be this way. In a previous post, I explored what employees can do to navigate a tough time. This post focuses on how executives and senior leaders can make those tough decisions without losing the trust of their employees. Let’s dig in!

Don’t hide the pain - I still vividly remember this. Me, sitting in a massive auditorium, listening to the new president of our company. I remember their suit looking very expensive. Sorry, I digress.

This was sometime in 2009, and the housing bubble was very close to bursting. The newly hired president talked about how well things were going and also requested feedback from the employees on how to improve our work lives. A few weeks later, the firm laid off 3,000 employees and, in the course of the next year or so, laid off another 6,000. Every time I heard about a colleague being let go, the president’s fake dog and pony show ran through my mind. Why didn’t they just tell us the truth?

Executives often think of their employees as temperamental children. One misguided reason senior leaders tend to hide the truth about how the company is doing from their employees is that they fear employees will start focusing on the worst-case scenario and stop being productive. Well, guess what? They’re already thinking about it! Another reason executives tend to gloss over the truth is that they worry employees will start looking for new jobs and stop being productive or that the company will have a capacity problem because employees will bail en masse. Well, tech employees are already doing that anyway, recession or not. Tech employees are constantly seeking greener pastures.

I treat my team as adults. I tell them when things aren’t working. If I miss my numbers and get yelled at by my board, I tell them. If the company is in financial trouble, I tell them. I know different executive teams and companies have various thresholds for sharing bad news, but I would recommend against not sharing any news and then turning around to do a layoff. The only thing I wouldn’t share is personal information like individual salaries, but aside from that, I’m fairly transparent with my teams.

Have a clear call to action - You can’t show them pain without offering the remedy as well. After sharing the company's precarious situation, provide your team with a way forward. Whether it involves putting in more hours, pivoting to a new roadmap, or whatever the case may be, let them know how they can contribute. In my experience, even the most disengaged team has a 50% chance of getting fired up again when you put them under pressure, give them a clear goal, and ask them to hit it. If you don’t have a way out, be honest. If the company is facing bankruptcy, tell the employees what’s happening instead of stringing them along or, worse, sending them on wild goose chases that lead only to disappointment.

Make yourself available - During moments of crisis, it’s important to spend time with your team. Set aside time to meet with them regularly and provide consistent updates about what is happening with the company, whether the team’s efforts are helping turn the tide, future next steps to take, the competitive landscape, or anything else that could assist your team in making better decisions to navigate the crisis. When I engage my team in crisis resolution mode, I hold a weekly meeting with the entire team where we review the work completed, address blockers, and answer any questions they may have. Lastly, many leaders I coach dislike taking on the role of a therapist for their teams. Unfortunately, during crisis situations, it’s a necessity.

Be Human - If everything fails and you have to let people go, close the entire company, or sell your business at a bargain price, remember that the individuals you are about to let go are real people with lives, families, dreams, and aspirations. Try to do the right thing by them. Provide as much support as you can through severance, COBRA coverage, and placement services. I also extend my network and connections to those I had to let go and direct opportunities their way. Please do the same if you can. And please don’t lay them off via a mass email or a group Zoom call.

Until next time!

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Leadership Coaching - If you are an engineering or product leader and want to learn how to make high velocity decisions under pressure, shoot me a note at info@maheshguruswamy.com. I am limiting the number of coaching clients I take on, so don’t wait :)

Book - If you are struggling with how to navigate messy leadership conversations and haven’t picked up my book https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN …tsk tsk tsk. Just kidding, please buy my book :)

A few things have helped me navigate recessions. I didn’t just survive recessions; I actually got promoted. This post explores the concrete steps software professionals can take to recession-proof their careers. Spoiler alert: Learning new tools is not one of them.

Optimize for delivery - The modern tech industry has always rewarded speed. From the early 2001s to now, every leader of every successful company has pushed for speed. I know the purist readers who are reading this will start yelling through their screens about technical debt and how running fast will cause more things to break. However, the reality is, if you complain about technical debt in a downturn and how the company is not paying attention to it, you have inadvertently put yourself on the layoff list. Fix the technical debt during peace times, not war times. Make do with what you have.

Individual contributors and leaders who push for delivery, time to market and rapid iteration will always make it to the lifeboat when the levee breaks. Also, it isn’t just enough to just do the work. Be vocal about your philosophy around speed. Share it with your team and leaders. If you are seen as an evangelist for speed, the powers to be will always have a tough time putting you on the layoff list.

Understand the business - A common mistake that individual contributors and some leaders make is to block out what is happening around them so that they can focus on the tasks in front of them. It isn’t a bad strategy, but in a downturn, it is very easy to stand out if you understand the macro conditions and how they are affecting the business. When leaders see you making decisions that are beneficial for the greater good of the company, they will understand that you are doing your part to help the company navigate the downturn as opposed to just letting the ‘higher-ups’ deal with it, which is what most employees end up doing. It is very hard for a leader to put a mission-oriented person on the layoff list.

Build/strengthen internal relationships with leaders - This might be a slightly harsh take, but I am basing this mostly on what I have experienced. When individual contributors and junior leaders talk to senior leaders or executives, it is almost always a variation of these questions

1. What is happening with X? X could be the company, a competitor, a project, the economy, etc

2. Will X happen to me? X could be layoff, promotion, return to office, etc

3. A few smart ones will ask, What is keeping you up at night?

However, most people don’t ask the one crucial question that will help you form an instant bond with the leader you are talking to, and that is-

What can I do to help?

I can almost guarantee that these simple words will make the other person (leader or not) your instant fan. It shows that you are putting somebody else ahead of you. It shows that you care. Leaders, managers and executives invest a lot of time (or atleast they should) in taking care of people and answering their questions, and when you flip the script on them and offer to take care of them, they will automatically put you in a different (and better) category of employees than the rest.

Network, network, network - Carve out time in your day to network online. Follow the leaders you like on LinkedIn/Substack, engage with their content and don’t hesitate to connect with them. When you connect with them, don’t turn around immediately after and ask them for a job. Just tell them that you like their content/advice and want to become part of their professional network. Worst case, they ignore your connection request. Best case, you have a connection you can reach out to when you need it. Almost 85% of jobs are filled through personal or professional connections.

Engage with recruiters - I would bet a dollar that a lot of you readers think that recruiters are the scum of the professional world. They cold message and call you about roles that you are not a good fit for at all. They leave you long voice messages that you immediately delete. Maybe some of you have been tempted to complain about recruiters on LinkedIn. Maybe, just maybe, some of you actually have publicly complained about them. You can get away with all this during peace times and when the economy is doing well. But you know who might be able to help you when the market turns? Recruiters.

When I receive inbound emails or requests from recruiters about roles that do not interest me, I always respond politely with my current and future career goals. Be courteous to recruiters and clearly communicate your career aspirations. You never know what cosmic connections the universe might manifest. And please, do not complain about them publicly. While it might give your ego a temporary lift, you will have alienated a network of influential people who could assist you in finding your next job.

Start with a yes - Engineers often have a bad habit of starting with a ‘No.’ When faced with a big project or a problem, or even trying out something new (like GPT, for e.g), even the most experienced engineers sometimes focus on how it cannot be done. They cite reasons like not having enough time, too much technical debt, or a lack of people.

If you want to ensure your place in the lifeboat, start saying ‘Yes.’ I’m not suggesting you have to agree to impossible projects with impossible deadlines. Saying ‘Yes’ opens a door for negotiation, allowing you to discuss time, cost, or both. Remember that with a long enough lever, you can move the earth.

Lastly, these are things you don’t do after a recession kicks in. You do all this well in advance. And because nobody can predict a recession, my recommendation would be to do this every day. You never know when it might help you.

Until next time!

P.S - For new readers, If you are a manager and are struggling to deliver bad news, my latest book will help. Get it here https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

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I am not sure how it is right now, but being an average kid in a middle-class South Indian household is not for the faint of heart. Constant scarcity is a bitch and the parents pushed their kids hard into a path that they thought led to prosperity. Growing up, I only had two choices. Become a doctor or an engineer. In all my time as a kid, I was never asked what I wanted to be when I grew up, and after some time, I just stopped thinking about it. I just did what my parents asked me to. I went to all the extra-curricular activities they signed me up for. I let them move me to different schools without throwing a fit. I went to all the extra tuition classes they signed me up for. In the end, it didn’t change a thing. I was an average kid through and through. The only thing I was good at was languages. I loved (and still do!) reading and writing. In hindsight, maybe I should have been more vocal about what I wanted to do. This is something I am acutely aware of as a parent myself. Instead of vicariously living through him, we encourage him to try out different things and push him to double down on the things that stick. We also let him fail and not yell at him for not being good at something that WE thought he might be good at.

My parents always thought I was special. I was. Just not in the way they thought.

Even though I was average, I wasn’t terrible. I scored just enough to graduate high school and a decent enough score to make it to an average engineering college. However, once I graduated, I decided that I needed to leave India if I truly wanted to find my path. I scored decently (average again!) in the various entrance exams that US colleges needed, and I made my way to the States along with a few of my friends. I landed at Wayne State University in Detroit!

When I mention to people I got my Master's degree from Detroit, their immediate question is, “Whoa, Detroit?? Of all the places in the United States, why Detroit???”. The reality is, I didn’t think too hard about where I wanted to go. All I wanted to do was get out of India so that I can clear my head, and I went to the first University that said yes to me. If memory serves right, I believe I also got into some master’s program in Colorado, but it was more expensive than Detroit.

Detroit is a difficult place to survive, and I give the city and its people a lot of credit for reshaping my worldview. Working minimum wage jobs alongside struggling families who were working multiple jobs made me humble and activated my survival skills. If a mother and father in their mid-thirties, working minimum wage jobs with two young kids can make life work, I could do it too.

I had enough money to survive a semester and a half at Wayne State, but I had made up my mind that I wouldn’t ask my parents for any help, because doing so would mean giving up my freedom. I wasn’t smart enough to become a research or teaching assistant or earn a scholarship, so I flipped burgers at McDonald's and maxed out my credit cards. I am pretty sure my family was embarrassed of me, but I didn’t let any of that affect me. The only thing that mattered to me was that I am in control of my destiny. I now believe that people (especially young ones) need to experience some hardship in life.

Hardships activate your survival and adaptability skills.

I would not exchange my time in Detroit for anything in the world.

When I graduated from the Master’s program, the job market was completely dead. It was 2003/2004, and the world was still recovering from 9/11 and the dot-com bust. Many friends moved back home due to the lack of jobs. I was determined to make it work because I had no interest in returning home. I joined a small consulting firm that placed me in Wisconsin, working for an insurance company to do some Java work, from which I was promptly fired. There is something sobering about being let go for incompetence. This was the first time my ego was activated. I decided that I wouldn’t grovel or badmouth the boss who fired me, but instead figure out how to succeed in my next role. I found another consulting gig, but this time I hit the books. I spent hours reading the existing codebase. I didn’t turn down any tasks and met all my deadlines. What I realized about myself was that when sufficiently motivated (which I was after getting fired!), I was a quick learner and even quicker at producing results. I wasn’t the smartest software professional in the room, but I could outperform everyone because I took the fastest path to completing tasks, and to my surprise and delight, that’s what companies wanted

This is where I learned that producing results will always surpass academic purity or perceived smartness in corporate America.

So, with my ego fully activated and with my knowledge of how to succeed as a developer in tech, I set out to climb that ladder and climb I did. I made it all the way to Software Architect, which in current times equates to a Staff/Principal engineer. Being a software architect is 90% cat herding and 10% coding. My boss back then helped me understand that I am pretty good at building interpersonal relationships and convincing large groups of stubborn people to do something they don’t want to do. However, I also realized that there isn’t much of a ladder to climb after software architect. As an immigrant who grew up in scarcity, I wasn’t ready to just accept the fact that I might have hit my career and compensation ceiling. So I decided to pivot to management.

Switching to management was extremely challenging. Keep in mind this was right after the 2009 recession when no one was hiring, and those who were needed experienced managers. No one was willing to hire me. I cold-emailed countless hiring managers. Although most of these attempts were unsuccessful, I established some valuable relationships with leaders I still keep in touch with. I determined that the best strategy was to move laterally, which didn’t grant me the engineering manager title but offered me valuable experience. I navigated through various companies while on a work visa.

Moving jobs while on a work visa is challenging. Your visa isn't transferable, so the hiring company must apply for your visa from scratch, and it costs them thousands of dollars. Additionally, each time you change companies, you lose your position in the green card (permanent residency) line. I believe all my lateral moves likely delayed my green card by about 5 to 7 years. However, I have zero regrets. Each of those lateral moves provided the right experiences and led me to my first engineering manager job, where a supportive boss gave me my chance. Jeff R, if you’re reading this, thank you! Those lateral moves helped me save about 5 years on my journey to an executive role.

Don’t hesitate to take risks and make some lateral moves if it will eventually lead you to what you are looking for.

It's worth mentioning that I was able to make these moves because of my support system, especially my amazing wife, who stood by me through it all. With the right support system, you can realize even your wildest dreams.

As I began managing teams, I realized that I couldn’t depend solely on my ego and my own methods of getting things done to make my team productive and cohesive. I can’t simply do all the work myself for my team, although in the early days, I did that quite a bit and frustrated my team to no end. I needed to change. I needed to learn new skills. I thought about pursuing an MBA, but ultimately determined that it was too expensive and I probably wouldn’t be a model student, given my history with academic success, lol.

One thing above all helped me become a good manager: books. I have always been a fast and voracious reader, which enabled me to absorb a lot of information in a short amount of time.

Books are not the only way to learn something new, but I have found that a well-written book, nine times out of ten, has been more useful than online posts or social media sound bites. So, if you want to learn something quickly, grab a book.

The books that dramatically shaped my management style are :

1. How to Win Friends and Influence People - How to build relationships.

2. One Minute Manager - How to be an effective manager

3. The Effective Executive - How to operate like an executive (I guess I was thinking about the future :) )

4. First Break All the Rules - Management frameworks for the post-industrial era

5. Drive - How to motivate people

6. Turn the Ship Around - How to convert task followers into problem solving leaders

I also read an HBR article in which the writer argued that managers need to be more vulnerable with their teams, which encourages employees to open up. The writer also said that managers should own up to their mistakes, which encourages employees to be self-critical. It was complete serendipity that I came across that article, but that single article impacted me tremendously and has definitely shaped me into who I am.

Be vulnerable, transparent, admit to your mistakes, and learn how to apologize. When done consistently, your team will do the same. Teams have a funny way of reflecting back what you give them.

My ‘graduation’ from engineering management was my time at Amazon. If you have the option to go to Amazon or pursue an MBA, choose Amazon. Amazon’s culture (which isn’t for the faint of heart) will transform specialist leaders (engineering leaders, product leaders, etc.) into business leaders. This is where I learned how a technology business actually operates. I learned everything from assessing the size of the opportunity to determining the TAM (total addressable market) for a feature or product, how to align stakeholders, how to execute through a team, and how to launch it in the market. I also got promoted and began managing other managers. Things were good. So good that I decided to pivot.

My friends told me I was crazy to leave such a great job. They weren’t wrong, but I also had zero interest in slogging at a company for a decade plus and hope to become an executive or a senior leader. Also, Alexa had grown from just a thousand people when I joined to close to ten thousand people in just three years and had become a giant bureaucratic machine. I wanted a faster path to the C-Suite. That’s when Smartsheet came along.

Smartsheet was a relatively unknown company in 2017. They were looking to hire an engineering leader who could build out an east coast development hub for them. I interviewed with them and I got the job. The next few years was a ride of a lifetime. The company IPO’d a few months after I joined and its growth took off. I was able to build all the high value leadership skills that I needed to break into the C-Suite in an extremely condensed time frame. Skills like:

1. Recruiting at scale. By the time I left, my org was north of a hundred people across multiple geographic locations.

2. Help define and enforce company culture

3. Helping set department level goals, including figuring out input and output goals.

4. I learned from top executives. My bosses gave me immense responsibilities and freedom, including allowing me to run both product and engineering!

It was a challenging job, but I enjoyed it and was fairly successful at delivering value through a tightly-knit team that I built from scratch. If I had to highlight a few things I did that contributed to my success there, they would be: a) Building relationships with key leaders, stakeholders, and customers, b) Never starting with a ‘No', c) Encouraging bottom-up thinking, d) Learning how to hire good leaders.

Eventually I got promoted to VP and……Covid happened.

After spending more than a year under lockdown, we (my wife and I) decided to get out of snowy Massachusetts and move to sunny California. I started looking for CTO gigs in Southern California and got randomly connected to Kajabi through a common connection. I interviewed there and got the job to run engineering. This is where I fell in love with the creator economy, which eventually led me to Everette and Kickstarter, where I currently am the Chief Product and Technology Officer running both product and engineering.

I am rapidly hurtling towards the end of the career arc I am on right now. I am not sure what the future looks like, but I hope it involves a lot of writing, teaching, and helping. I am on a mission to send the ladder down to others who are were I was five or ten years ago. All you have to do is ask. Readers, if you want my advice on anything, start here https://intro.co/MaheshGuruswamy.

P.S - For new readers, If you are a manager and are struggling to deliver bad news, my latest book will help. Get it here https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

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