It’s the dream, right? A sea of senior PMs, each owning “big strategic initiatives,” working hand-in-hand with leadership. No hierarchy. No bureaucracy. Just freedom.

Except… There’s a catch.

Watching teams rise, stall, and quietly burn out, I’ve noticed something. And I want to alert you to my findings. When you flatten the structure, you don’t remove the work of management. You just hide it.

The Myth of Middle Management

In big companies, middle managers often don’t manage people. They manage information.

Who knows what. Who should know what. Who forgot to tell someone something.

It’s messy, repetitive, sometimes absurd, but it’s also what keeps an organization moving in the same direction.

Now, imagine AI taking over that role. It’s already trying. We’ve got AIs writing emails (the kind you’d rather have another AI summarize for you), updating dashboards, and “distributing context” across teams. The promise? Information flows perfectly. No middle managers needed.

Sounds elegant. Almost utopian.

Until you realize that when you remove the people who carry context, you also remove the people who care about it.

What Actually Happens When You Go Flat

You end up creating an organization for senior PMs only.

You eliminate paths for growth because when everyone’s a “lead,” the only way to move is sideways. Or the highway.

You drain domain knowledge over time because your top people move on and you have no juniors to train.

You raise the risk of burnout because without clear support structures, autonomy starts feeling a lot like isolation.

And worst of all, you erase the one competitive advantage humans still have over machines:

The ability to care.

The Void Behind the Title

I’m not saying we need more layers. Nobody wants that.

But when you remove a title, you also remove the work behind that title. And unless someone deliberately fills that void, the team starts to drift.

Flat doesn’t mean leaderless.

It just means the leadership work gets redistributed, usually to the people least equipped or least willing to carry it.

Leave the Team Better Than You Found It

There’s an old Scout’s rule in coding: always leave the code cleaner than you found it.

Maybe leaders should do the same… with teams.

Because if you flatten everything so much that nobody’s left to shape, grow, or protect the people doing the work, you’re not building a stronger system. You’re just erasing the parts of it that make it human.

A group of cunning con artists is constantly spotting new marks. Mickey Bricks Stone is the head of the crew, the mastermind. His crew is a blend of unique skills: Albert Stroller, the seasoned grifter; Ash Three-Socks Morgan, the team’s tech genius; and the newbies in the team, the Kennedy siblings, Emma and Sean.

Carlton Wood and Harry Fielding, two greedy traders with intellectual property rights, crossed their path. These men tricked a trusting man into a deal where he lost control over the cutting-edge security technology he created. Despair led the man to suicide. Mickey’s crew decided to take revenge.

The stolen invention? A theft-preventing security device for art galleries. Wood and Fielding closed a lucrative deal with an art gallery in London but lost an advertising agency due to Wood’s volatile temper. That was the opportunity for Mickey’s team. Pretending to be PR experts, they tricked Wood and Fielding into a very risky PR move: “With our technology, insurance is obsolete. The painting is theft-proof.”

Wood and Fielding agreed. The con was on.

Now, it’s easy. They just need to steal the painting, let Wood and Fielding pay the finder’s fee, and disappear with the money. Ash is the tech guy. He gets them anywhere, even into a secured gallery to steal an unstealable painting.

But not this time.

The system is really good.

They can’t steal it.

“Just get us in,” Mickey said. “I’ll handle the rest.”

Days later, in the early morning, Wood and Fielding got an unpleasant call from the gallery.

“The painting is gone!”

But how? Wasn’t it impossible to steal it?

Here’s where creativity and strategy come in. There’s a technique called "What if." You can use it for problem-solving, too. Start by defining the rules.

The rules of this con?

The security system stays, no theft insurance, and they must steal the painting to claim the reward.

Once you have the rules, you ask, “What if…?”

What if they don’t steal the painting?

The last step is “Imagine if.” Visualize a scenario where this could work.

They don’t move the painting. But they need to make it look like it was stolen. No need to have the painting in their hands, just an empty wall in the gallery.

What if we build a fake wall in front of the wall with the painting? The gallery thought it was stolen, but it never left.

Next time you face a seemingly impossible challenge with your team, try to think of the fake wall. And ask yourselves, “What if…?

The wheel is spinning, but the hamster is dead.

We all know that.

You’re in a meeting. It’s your fifth or sixth or seventh (!) in a row that day.

And then suddenly…

Click…

Autopilot: ON

The lights are on, but the pilot is asleep in the back. You don’t feel awkward in that moment, but you will in a second.

Make no mistake, being able to focus helps us succeed. It helps us get the right work done. Yet, it’s increasingly challenging, especially in a corporate environment where meetings just keep piling up to eternity.

Psychologist Michael Lipson discovered that we can learn to sharpen our focus by understanding the patterns of losing it. In short, we must know how we lose our focus.

Two skills define a mindful mind – focus and awareness. Focus is our ability to concentrate on this thing, right now. Awareness is our ability to notice that we’ve lost focus and be at ease with it. Only then can we bring our mind back to focus.

But let’s be practical. What to do when in a meeting?

1. Keep each other present. The collective genius comes when everyone in the room is fully present. It’s each team member’s responsibility to bring the best of themselves and make sure the rest do the same. When you notice a lapse, just say: “Should we slow down or repeat that?”

2. Do a little mindfulness exercise. Take two minutes before the meeting to focus on your breath. Or you can even start the meeting with two minutes of silence so that everyone in the room can attune to this particular meeting. If you can, finish the meeting five minutes before the hour so that everyone has a bit of time to rest.

3. Don’t plan seven meetings for one day. It’s a creativity killer.

But wait…

Maybe you don’t have to be in this meeting. What if you just leave?

Coincidentally, a short movie, Cars Toons, had been planned for release at the same time. Their computing capacity couldn’t handle both projects simultaneously.

Greg Brandeau, the senior VP of system technology, had two choices: spend $2 million on new computers or delay Cars Toons. With time running out and pressure mounting, he turned to Ed Catmull, Pixar’s co-founder and CEO.

“I don’t see how we’re going to get out of this mess,” he said. “Ed will have to make a decision.”

Catmull listened without a word, then asked a few questions and shared his view: “We don’t have $2 million for new computers.”

Brandeau expected this answer. “Then, do we delay Up or Cars Toons?”

“Neither,” said Catmull. “We need both done on schedule. See if you can figure something out.”

Brandeau returned to his team, desperate.

After seemingly endless discussions, someone suggested, “Can we borrow Disney’s computers and use them here?”

Disney had acquired Pixar a few years before, but the two companies did not share their resources. Disney had its HQ in Burbank, and Pixar was still in Emeryville, almost a full day’s drive away.

“Insane!”

But they did it anyway.

The team trucked 250 of Disney’s RenderFarm computers and rendered both movies in time for the release date.

There are two kinds of decisions: either-or and both-and. Either-or means compromise. Both-and means combining the best of all options. Catmull refused either-or. Spending an extra $2 million or delaying the release date were two bad options. He pushed for the best solution.

Quick decisions may speed up the process, but they lead to mediocrity. The real challenge and excitement in creative work lie in holding conflicting ideas and combining them in a novel way.

Decisiveness is overrated.

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