I’ve been reading about flat organizations and teams disappearing on LinkedIn for a while. Now I’ve seen our own plans, and the earth under my feet is going flat: no more teams as we know them, almost no hierarchy, and for me, 100% individual contributor work. Gulp.
I’ve seen it coming, and I’ve helped build some of the workflows that will make it happen. Funny, isn’t it? If everyone is doing it, it must be right, right? The whole thing reminds me of Prince’s “When Doves Cry.” It has a great beat, it gets stuck in your head, and you can dance to it for a good while before you notice it’s a sad song.
Don’t ask me too much about Prince, though. I like his music, but apart from two or three songs I’m no expert. I got curious after reading Ready Player Two, Ernest Cline’s sequel to Ready Player One, and his music has been stuck in my head ever since…
I’ve always seen myself as a leader first and a manager second, for the stuff that actually needed managing. I rarely push; I’d rather pull, guide and coach people until they get to their own aha. I never liked enforcing processes for the sake of processes, or pushing people around schedules. I’d rather give them options, and let them choose and take ownership. That all came with the management role, and I’m sad at the thought of losing that part of my work.
The king is dead, long live the king. The old king dies, the new one takes over, and everyone knows whose name comes next. (Grim, but very efficient.) I know my new role will be individual contributor work, but I’m still working out what happens to the leadership work I’ve spent years learning to do. Who helps people develop and work through problems together when teams look completely different and no manager is responsible for them?
At the bridge
In August I wrote about grieving in advance: “The mistake wasn’t reading the prophecies or taking them seriously, but treating them as settled fact and grieving in advance.” I still believe a group of agents is a toolchain, not a team. And I believe in not worrying about a bridge before you get to it.
Well. I’m at the bridge now.
Last week I had to say goodbye to people from my team. Letting people go is one of the things you also have to do as a leader, when the time comes. If someone has performance issues or isn’t a good fit, saying goodbye is easier. This was different. I’ve never looked at people as just numbers, so it’s personal. I’d been sitting with these people and watching them grow. It’s almost like breaking up... no, it is breaking up. It’s also why I kept putting off finishing this draft, or any draft. This essay is my tribute to the time with my team, like the last chapter of a book. There might be a sequel, but you never know when, or how.
At the end of the August essay, I said the people and the culture, the thing between the chair and the computer, would stay front and center in what I write. That hasn’t changed. Teams as we know them might disappear, but the ordinary, messy, human work won’t, and I’ll keep writing about it. What has changed is that the restructuring is starting, and I don’t know what our organization will look like in a couple of months.
Teams are getting flatter, and flat teams don’t need as many managers, maybe none at all. In a small company, the leading part was most of the job: helping people grow, unblocking them, brainstorming with them, doing sanity checks and reality checks.
Am I in a bubble?
I’m hardly a neutral observer. I work with AI agents every day, I love what they make possible, and I’m building workflows that replace some of the work people used to do. When that’s your normal, it’s easy to mistake it for everyone’s normal.
I checked whether I’m in a bubble. In July, Menlo Ventures surveyed 5,067 US adults, and only a quarter of them use AI every day. Three out of four don’t, and I’m not even in the same building. At work it’s lower still: in Gallup’s panel of US employees this spring, only 15% used AI daily.
So yes, I’m in a bubble, a bubble of intensity. People outside it are worried anyway. The same Menlo survey found that 43% of working adults see at least a moderate risk to their own job in the next five years. You don’t have to use AI every day to worry about what it’ll do to yours.
The polite word for people like me
Big companies doing layoffs keep saying the same thing. When Amazon announced about 16,000 role reductions in January, the message talked about “reducing layers, increasing ownership, and removing bureaucracy.” Layers, in case you’re wondering, is the polite word for people like me. Block went further. In From Hierarchy to Intelligence, which I argued with in April, Jack Dorsey and Roelof Botha write that “there is no need for a permanent middle management layer” and that “hierarchy and middle management impede information flow.”
I read a lot of LinkedIn posts from big-company leaders about removing management layers. That’s the ironed shirt. What you don’t read about is the dirty laundry: who picks up the work that still has to be done once the layer is gone. At a smaller company, that was often me. I kept the stuff I didn’t want to burden my team with, because somebody had to do it.
The other trend I keep reading about is going flat and stripping away titles. Self-managing teams are all the rage right now, but they only work when certain conditions are already met. Here are some of them off the top of my head: trust, leaders who actually let people do the work instead of telling them to feel empowered, and working agreements people actually define themselves and respect.
Not every company has those. Stripping titles before the foundation is there is like putting icing on a cake that’s actually… minestrone soup.
Flat also has a way of ending up like Animal Farm: all animals are equal, but some animals are more equal than others. If we’re all equal, who approves the time off? Who sorts out the logistics, or decides when two people want the same week in July? Somebody still has to.
For some of us, the title is a badge of honor we fought for, a milestone that shows the outside world we ground our way here over decades, starting from zero. It’s not the only thing that matters, but for me, it is important. Losing it is not super motivating, and not super role-model-like either. What does it tell the people coming up behind me about where the ladder leads? And what does it tell the women in tech, who don’t see that many women with a leadership title to begin with?
A team that needs me less
I keep hearing that leadership will become even more important in the age of AI. I want to believe that, I really do. And the optimists have a point. Clarity in messy times is about to get scarce. Humans who are scared about their jobs will still need to hear this is where we’re going, this is why, and this is what we’re not doing, and so will the agents, who will happily go wherever you point them, including off a cliff. None of that requires a management title.
Meanwhile, Gallup found that the average number of people reporting to a manager in the US grew from 10.9 in 2024 to 12.1 in 2025. I wouldn’t pin that on AI, but it points the same way as Amazon’s layers: fewer managers, each with more people. With twelve people, you either book your 1:1s a quarter in advance, like the dentist, or drop them completely. And then what?
Leadership as a practice survives, then. What I’m not sure about is the version I know, the one with a team, a ladder and a title. I like the difference between leadership and management, and I’ll admit it’s comforting: if it’s management that goes away, the leader in me is safe, right? Not really. Leadership matters doesn’t tell me how many leaders a company will keep or hire. A company can love coaching and still employ fewer people whose job is to coach.
It also doesn’t tell me whether I spend my own time well. When people come to me, is it because I help them decide better, or because the process says they have to stop by? When I turn a vague request into something the team can work with, is that clarity, or am I a very expensive interpreter?
What do I actually do in a normal week, besides the coaching and my own IC work? I sort out conflicting priorities and bring context where I see a gap. I try not to be the person who approves every decision, but when we need to push something forward and nobody wants to own the trade-off, I own it.
Am I bad at delegating? Or am I good at seeing the stuff that glues work together, so my team could spend its time on what they knew best, which was programming? And once my role is gone, who ends up carrying that glue?
I never wanted to be a required stop. My dream is a team where I can say do your magic, and they pull me in only when they’re stuck, or need a fresh perspective or someone with different experience. If I made myself necessary just to prove my value, I’d build exactly the dependency I’ve tried to avoid.
Describe that dream to someone just counting layers, and they hear a team that needs me less. (I’d call that good management. A CFO might call it a business case.) If people can disagree, make the trade-off and move on without me, great, I can leave them to it. If they can’t, they’ll need help getting there.
So what’s left when the managers are gone? Only the top leadership, and everyone else flat underneath? Or will we start adding levels back into the sameness of the titles, until we’re back at Animal Farm?
Who teaches the next ones?
Most of what I know about leading people, I learned from some wonderful people and from my own mistakes, made on real humans who had real reactions. An agent won’t sulk after a rough conversation. It won’t lose trust in you because you took credit for its work, or tell you over coffee that the last reorg scared it. It won’t grow, either, at least not in the way a person grows when someone takes the time to stretch them.
I feel bad for junior roles. An agent needs about the same training a person does, in a lot less time. It doesn’t forget what you told it, and it doesn’t need the human side of onboarding, so on paper it looks cheaper than a junior, even if it’s probably less creative. That’s the math I expect a lot of companies to run, and it leaves less work for juniors. And with each manager carrying more people, there are fewer manager roles to grow into, so fewer juniors will ever get a first shot at leading anyone.
How will the next generation learn to lead people, if they spend their careers managing agents? Delegation, writing a good brief, reviewing the output... sure, they’ll be great at that. But trust? Conflict? Knowing when to step in and when to get out of the way? Where do you practice those when your team is you plus a dozen processes that never get tired and never push back?
A cog with opinions
I’ve spent part of this essay on other people: my team, the juniors, the ones who’ll have to learn to lead without anyone to practice on. But this essay is about my world and how I see it. Sorry, but not sorry. Maybe it’s also a little about you, fellow leader, current or former.
In my world, I’m also one of the people building the agents. If I automate myself out of the equation, what’s left? I’m hoping it’s the parts agents are bad at, the awkward conversations and the aha moments. Most engineers I’ve worked with would rather not deal with the human stuff at all. I actually like it. But will I still get to do it, or am I one of the cogs in a big machine, busy optimizing the machine that’s about to optimize me? (At least I’d get to write my own documentation, and an agent would actually read it.)
I might have helped turn myself into a cog, but I still have opinions, and I’m not afraid of sharing them. Keeping them is how I stay true to myself and to what I’ve learned about systems. Someone has to be the kid pointing out that the emperor’s bottom is bare, and I’d rather it’s me. And I’d still like to at least try to build a better workplace for humans, even if more of the work ends up done by agents.
Formerly known as
Prince has more to offer here than a sad song with a great beat. In the nineties he swapped his name for a symbol nobody could pronounce, and for years everyone called him The Artist Formerly Known as Prince. He didn’t stop making music while his name was up in the air, and eventually he took it back.
I’m planning to keep writing, too. This week I had to decide whether to renew the domain for this newsletter, and I had some serious thoughts about whether it’s still relevant. I renewed it for another year, to see where the writing takes me. So whatever my title ends up being, you’re stuck with me for at least twelve more months.
The version of leadership I know is dead. Long live whoever ends up bringing some clarity when everything’s a mess, with or without a team, with or without a title. Name to be announced. Maybe a symbol? I already have one, check the logo. Unlike Prince’s, mine you can pronounce: BCC. Use that when you recommend it to friends. No pressure. (Some pressure.)