The Future of Management
What management looks like on the other side of the waterfall
According to Dante, fortune tellers are punished in the eighth circle of hell, and their punishment is for their heads to be twisted backward so that they are perpetually walking backward because they tried to see too much in the future. It is one of the reasons I have never really made predictions of the future. However, when it comes to management, I think the future is somewhat already here, so I am going to make an exception and dig into what the future of management might look like once we have successfully gone over the waterfall of AI, financial discipline, and economic uncertainty and land in calmer waters.
The Middle Falls Out
One of the many incorrect assumptions companies and leaders made during the free-money era was that hiring more people would always result in growth in the long term. So companies hired like it was nobody’s business, hoping that each person hired would extend the footprint of the business. They hired managers to manage the people, and then hired managers to manage the managers, and more managers to manage those managers, and so on. This era of excess gave birth to middle management.
However, the future didn’t pan out exactly how companies thought it would. Even before the post covid/AI reset, middle management didn’t actually become what companies hoped. It didn’t become incubators for new lines of revenue-generating businesses. Those leaders primarily became a pass-through. They didn’t have any real decision-making powers, and they ended up managing processes, keeping their people happy, and generally becoming good at saying “no” to anyone who wanted their team to do something that wasn’t on the roadmap. To be clear, this wasn’t the fault of the middle managers. They were merely trying to navigate a world created by their bosses. The bosses ended up holding onto their decision-making powers instead of delegating them as they should have. Then came the double whammy of post-COVID hangover and AI-driven disruption.
When companies needed to save cash, they started asking the question, “What does this person do, and can we make do without them?” and it was clear that the middle management was mostly a nice-to-have. The only thing middle management was somewhat good at doing was managing the employees on their team and making sure they were motivated and productive. However, when companies started cutting down on expenses and started letting people go, there were fewer people left to manage, and the survivors could be consolidated under fewer leaders who actually had decision-making authority, which nicely segues into the next section.
A little pro-tip before we move on: If you are in a leadership role but don’t have any true decision-making powers…..it’s a trap.
From Process to Decisions
During the free-money era, along with the explosion of headcount and managers, there was an explosion of processes that purportedly allowed software development teams to move faster. There was the agile manifesto, which led to scrum, extreme programming, BDD (behavior-driven development), scaled-agile (somebody shoot me), six-sigma (shoot me again), and the list goes on. The biggest problem with all of these methodologies was that they assumed software development was like an industrial assembly line and tried to optimize each step. An entire cottage industry of process consultants, agile gurus, and six sigma black belts erupted overnight and has made billions in profits over the last ten years by convincing companies that all they need to improve productivity is a better process, which couldn’t be further from the truth.
The reality is, software development is absolutely not like an assembly line. You can’t test drive a broken car. You can absolutely test drive a broken piece of software, and your test customers will give you useful feedback you can actually use to make the software better. The bottom line is, the pace of software development is really only dependent on two things: 1) Do you have the right people? 2) Can those people make the right decisions? That is it.
And that’s exactly what companies are starting to optimize for right now. Instead of creating a layered hierarchy of managers and employees, where decisions can be discussed, debated, and killed, they are optimizing for flatter organizations with empowered leaders who can actually make decisions. The right decision isn’t always the perfect one. It is the one made quickly enough to matter, with enough conviction to commit to it, and enough humility to reverse it when the data says otherwise. That last part is what most companies still get wrong. They reward decisiveness but punish reversal, which trains leaders to defend bad decisions instead of changing them.
If you are a process-oriented person, better start retraining yourself to become a decision-oriented one. What I mean by that is….have a point of view on what the direction should be, not just instructions and guardrails to ensure the right decision gets made.
Wider Span of Controls
One of the things AI has almost completely destroyed is the day-to-day administrative burden of managing teams. One of my VPs currently manages about thirty people. He has agents connected to GitHub, Linear, Slack, and Zoom. At any given point in time, he can tell …wait for it…. whether the right people are working on the right things, at the right pace. Figuring this out even a year ago would have taken multiple meetings with stakeholders, peers, his own team, etc. One of the biggest reasons the manager-to-employee ratio was pegged at roughly 1:10 is that it is the maximum number of employees a manager can keep track of and keep aligned towards the right goals. Any more, the manager starts to struggle to keep track of what’s going on. Because of this limitation, often, companies just tacked on a manager after the number of employees grew beyond 10 per team, without thinking about the long-term implications of adding a manager who would most likely want to own their own slice of the business in the long run, as opposed to acting as an overflow people manager.
With AI tools, this administrative burden has completely disappeared. I wouldn’t be surprised if the span of control of a single manager starts to exceed fifty employees. So, if you are a people manager and you are used to the 1:10 ratio, start leaning on AI to automate your administrative burden. And here is the harder truth: a manager going from ten reports to fifty reports means four other managers are gone. If most of your job is administrative coordination, AI isn’t your assistant. It is your replacement.
The End of the Career Ladder
One of the most negative side effects of a cyclical economy is that employee TLC is also cyclical. When the money is flowing, companies bend over backward to take care of their employees. Catered lunches, celebrities performing at the all-hands, onsite massages, and most importantly, a seemingly deep commitment to helping them achieve their career goals. For the last decade or so, companies and their managers have put in a tremendous amount of effort into helping their employees figure out their career aspirations, a roadmap to getting there, and spoon-feeding them help along the way. It isn’t a stretch to say that managers have coddled their employees. Why? Because when the money is flowing, opportunities are abundant, and employees (and not just the good ones) can easily switch companies, chasing more money, titles, etc. Some companies have gone so far in terms of taking care of their employees that they inadvertently (or maybe deliberately?) created a college-esque environment, where the manager has to ‘take care’ of their employees.
And here we are now. This time it isn’t just another turn of the cycle. The tech industry is maturing. Financial discipline is here to stay. And AI is going to reshape the industry in a way that, by my predictions, will compress salaries and headcount. Layoffs are going to continue. Take it all together, and combine it with the fact that companies are quickly moving towards flatter and wider organizations with fewer managers, and the days of your manager hand-holding you through your career are going to die a quick death.
To be clear, this doesn’t mean that managers will stop caring. The good ones will continue to care about their employees, but it will be on the employee to chart out their future and find opportunities (either inside the company or outside) that will help them get to where they want to go.
The bigger shift is that I think tech employees will increasingly start doing multiple gigs at the same time to hedge against a single W2 controlled by a single company. The implicit deal for the last twenty years was: give us your full-time loyalty, and we will take care of your career. That deal is breaking on both sides. Companies are letting people go faster and with less ceremony than they used to, and employees are starting to figure out that a single employer is a single point of failure. The smart ones are already running a consulting practice on the side, advising startups, building something of their own on nights and weekends, or some combination. This isn’t moonlighting in the old sense of hiding it from your boss. It is portfolio thinking applied to your career. The employees who do this well will be more resilient than the ones who don’t, and over time, I think companies will quietly accept it because the alternative is losing their best people entirely.
So, if you are a manager, stop coddling your employees and start treating them like adults. Don’t become a tyrant, for god’s sake. Treat them fairly and still care about them, but let them figure out what they want to do. If you are an employee, start planning your future on your own. Don’t think your company will do it for you. If you have the opportunity to take on a side gig, do it.
I know this section reads a little harsh, but as you all know, I don’t mince words. This prediction might never come to pass, but given the changes I am already seeing in the industry, I think it’s better to be safe than sorry.
Cross-Functional Leadership Wins
The specialist leader is becoming an endangered species. For the last two decades, the path upward was to pick a function, get really good at it, and ride that expertise as far as it would take you. Engineers became engineering leaders. Product people became product leaders. Marketers became marketing leaders. Each one ran their own kingdom, hired their own team, and protected their own turf. That model is breaking, and AI is the proximate cause but not the root one.
The root cause is that the work itself is becoming less functionally distinct. A product decision is also an engineering decision, a GTM decision, and a support decision. They were always intertwined, but the old model handled this with coordination overhead. You had a product lead, an engineering lead, and a marketing lead, and they met every week to align. The meetings were the price you paid for specialization. AI is now collapsing the cost of crossing functional boundaries. A leader who understands product, engineering, and GTM doesn’t need three weekly alignment meetings because they are the alignment. The decisions that used to require three leaders in a room can now be made by one leader with the right tools and the right scope.
I have lived through early versions of this myself. When I ran product and technology together at a previous company, it wasn’t a cost-saving move, although it did save costs. It was a speed move. Decisions that used to take a week of back-and-forth between two leaders took an afternoon. The trade-off was that I had to be genuinely competent in both domains, not just nominally responsible for both. That is the hard part, and it is the part most companies get wrong when they try to consolidate roles. They put an engineering leader in charge of product and call it a day, and the product org quietly falls apart because that leader doesn’t actually know how to run product.
What this means at every level is that the specialist track either disappears or gets compressed. The director of engineering who can also run product and design is going to outpace the director of engineering who only knows engineering. The VP who can hold three functions in their head is going to outpace the VP who can only hold one. The leader who can think across the whole business is going to outpace the leader who optimizes for their slice of it. This isn’t just an executive-level shift. It is happening at every layer of the org chart, and it is happening faster at the lower layers than at the top.
Becoming cross-functional is easy to advise and hard to do. If you are an excellent engineering manager who got promoted by being excellent at engineering management, the advice “go learn product and GTM” means leaving the thing you are best at and being mediocre at two new things for a few years. Most people won’t do it. They will defend the specialist model because it is the model they won under, and they will lose ground to the people who took the harder path. The T-shaped framing that was popular a decade ago is no longer enough. T-shaped meant one deep specialty and broad surface familiarity with everything else. What is becoming premium is closer to a comb. Multiple genuine specialties, not one with shallow exposure to the rest.
So, if you are a specialist leader at any level, start broadening now. Take on scope outside your function, even if it feels uncomfortable. Volunteer for the cross-functional problem nobody wants to own. If you are the person doing the promoting, start thinking about which of your direct reports could plausibly run two or three of your current functions in a few years. The ones who can are the future of your company. The ones who can’t are not bad leaders, but they are increasingly going to be capped where they are.
A pro-tip to close: if your scope is still a single function, the clock is ticking.
The Rise of Anti-Management Themes
When I was in middle school, our history teacher taught us about Alexander the Great and his exploits. I was completely fascinated by him and the fact that by the age of thirty, he had created one of the largest empires of that time. Even more fascinating was the fact that Alexander actually made it to the Indian subcontinent as well, facing off against a local king named Porus, who was the king of current-day Punjab in north-western India. Porus was a formidable opponent, but Alexander defeated him handily, and as Porus lay defeated on the battlefield, Alexander asked him how he, the victor, should treat him. To which Porus said -
“You should treat me as this day counsels you, this day in which you have learned how fleeting good fortune may be.”
In other words, Porus was warning Alexander that good fortune is fleeting and the victor today could easily be the vanquished tomorrow.
There has always been a power imbalance between management and employees, and this current pressure cooker environment of restricted capital and layoffs we are in will tip the scales even further in favor of managers. Senior managers will wield all the power, with employees wielding very little. However, as history has taught us, power seldom remains on the same side of the see-saw. Eventually, employees will start pushing back collectively. I have already experienced this with the tech union at Kickstarter. A deeper dive into my time with a tech union warrants its own essay, but what I can say is that it was deeply messy and created divisions inside the company, the likes of which I have never experienced before. My prediction is that tech employees will continue down the path of getting organized, and anti-management sentiment will continue to ratchet up.
So, if you are a manager, when you are making a tough decision, like a layoff or letting someone go, do it with grace and remember that you are affecting people’s lives. Push for better severance packages and longer COBRA coverage. And in general, be conservative about headcount in the future. You are the one who will have to undo it.
If you are an employee, remember that your manager is a human just like you. Calling them a fascist purely because the group you are affiliated with has decided that all managers are bad is not going to help anyone. If you want change, push for changing the overall system. Your manager (and their bosses) are only operating with the cards they have been dealt, and trust me, they have zero option to change the cards.
After the Waterfall
What I can say for sure is that the pressure in the system will eventually run out, and we will be in calmer waters. Will it be in 5 months or 5 years? I don’t know. But we will make it out of this. We can’t (shouldn’t) worry about things we cannot change, because it will only lead to madness. What we can do is change the way we operate. Know that a waterfall is coming and put on your life vest and grip the sides. It will be a rough ride.
P.S. - I have been dropping hints on socials that my course, aimed at senior leaders who want to prepare themselves for a dramatically different-looking future, Rewired for the Future, is almost ready. I am happy to announce that I have a launch date for it. 6/1. Mark your calendars.