My friend, Chris, e-mailed me a while back, frantic.
An e-mail had gone out to most of the people in his company. It arrived with the soft, apologetic tone of someone returning a sweater you didn’t realize you’d lent them. It used phrases like “flattening the organization” and “unlocking efficiency through AI.” It assured him that nothing important would be lost, which is exactly what you say right before something important is lost.
Chris’ boss, Greg, disappeared sometime between the second paragraph and the bulleted list. A few days have passed as of this writing. No one has mentioned him again.
We are, it seems, in the middle of a corporate cleanse, but not the kind where you drink green juice and regret your life choices. It’s the kind where companies remove entire layers of management like carbs. The idea is simple: fewer managers, more speed, and a generous sprinkling of AI to do the rest. It sounds fantastic, like switching from a station wagon to a sports car, it’s great in theory, until you realize no one taught you how to drive manual transmission, or handle the curves at 150 miles per hour.
What many organizations fail to realize is that management isn’t just one thing. It’s several things, bundled together like an overstuffed carry-on, and companies have begun throwing it into the overhead compartment without checking what’s inside.
Let’s talk about Greg.
Greg did three things, though Chris and his company wouldn’t have been able to tell you that at the time. They mostly thought he forwarded emails and asked how things were going, which I now realize is like saying a heart just “moves blood around.”
The first thing Greg did was move information around. Or, rather, was a central force in routing information and ideas.
Yes, this means the emails. The meetings. The “just looping you in” messages. This part, it turns out, AI is quite good at. Better, even.
Today, an algorithm can summarize a meeting you didn’t attend, flag the three things that matter, and send them to the five people who need to care, all before you’ve finished pretending to listen in the next one. If this were all Greg did, then yes … Goodbye, Greg. We wish you well in your future endeavors, perhaps in artisanal bread-making. Or social media influencing. Or becoming an influencer who makes artisanal bread.
Whatever it takes, Greg.
The second thing Greg did was he made sense of things, and this is where The Effectiveness of Greg (which sounds like the title of an R.E.M. ablum, now that I think of it) is harder to replace.
He listened to ten conflicting updates and told the team what actually mattered. He knew when a “two-week delay” was just a hiccup and when it was the first crack in something much larger. He could sit in a room full of noise and come back with a signal.
AI can summarize the ten updates, but it cannot yet tell you which one should keep you up at night. This requires context. Experience. The subtle, unsettling ability to say, “Something feels off,” without being able to cite a single bullet point.
Finally, Greg held people accountable (and occasionally uncomfortable (but, I repeat myself))
This is the thing no one misses until it’s gone. Greg told you when you were wrong. This wasn’t digital accountability, either, where the green, smiley face in the third column turns into a red, frowny face. It was the human kind. The kind that comes with eye contact. The kind that makes you sit up straighter and reconsider if not your life choices, at least your last email.
Greg was very good at this.
“He checked in,” my friend said. “He followed up. He remembered what you said you would do and asked, whether you had done it. If you hadn’t … Well, Greg would make sure you would.”
My fiend paused, then added: “but in a good way. Ya know?
AI can remind you of your deadlines. It can even send you a frowny face when you miss them. It cannot care whether you meet them.
Not yet, anyway.
After Greg left, something strange happened. Nothing broke immediately. That would have been too obvious. Instead, things … just drifted. Information flowed beautifully. Better than ever. The team had summaries, dashboards, automated insights. They were drowning in clarity, if such a thing is possible.
And yet, no one quite knew what to do with it.
Projects lingered in strange limbo. Decisions stretched out, like conversations at a dinner party where no one wants to be the first to leave. Feedback became optional. Accountability became theoretical; something people discussed (usually in conversations involving white boards), but never actually put into practice.
Again … much like removing carbs from your diet.
One morning, my friend realized he hadn’t spoken to another human about his work in three days.
“I was behind on all my projects, despite feeling like I’d been working harder than ever,” Chris said, “and nobody seemed to care. I had, however, received fourteen perfectly formatted updates explaining why everything was fine.”
“It did not feel fine,” he told me.
Across the business world, companies are trying different approaches to this brave new manager-less (or manager-lite, if you want to be kind) future. Some go fully flat. No hierarchy or titles. No one telling you what to do. It’s exhilarating, in the way jumping out of a plane is exhilarating. You are free. You are empowered. You are also, at some point, wondering who packed the parachute.
Others attempt a more thoughtful disassembly. They let AI handle the flow of information, assign specific people to interpret it, and keep a few humans around to coach and develop others. It’s less dramatic, but also less likely to end in tears.
And then there are those who simply compress management. This means fewer managers, more responsibility, and higher expectations. You are given autonomy and a reminder that failure will be noticed and dealt with accordingly.
Each model works, in its own way. Each also breaks, in its own way.
The mistake isn’t that companies are using AI. They should. The mistake is assuming that because one part of management can be automated, all of it can. It’s like discovering that a dishwasher can clean your plates, and then concluding that you no longer need a kitchen. Technically, yes, the plates are clean. But where did the meal come from? Who decided what to cook? And why is there a growing sense that something essential has been misplaced?
What companies often miss is that management is not overhead. It is infrastructure. Remove too much, and the system doesn’t collapse. It just becomes strange.
The future of management isn’t about putting Greg back where he was, albeit slightly more robotic (and much more agreeable, depending on the model you choose (I’m looking at you, ChatGPT)).
The future of management is about unbundling the role intentionally. Let AI handle information routing. It’s faster, cheaper, and doesn’t schedule unnecessary meetings. Keep humans focused on sensemaking. Put your best thinkers where ambiguity lives. Preserve accountability and feedback as a human function. Make sure someone still cares, out loud, about what gets done.
Most importantly, design for these functions explicitly. Don’t assume they will magically reappear just because the work still needs to get done. They won’t. They’ll dissolve into the background, and you’ll be left with an efficient system that no one quite understands and no one feels responsible for.
A few months after Greg disappeared, something unexpected happened. A new role appeared. It wasn’t called “Manager.” That would have been too obvious. It had a name like “Program Lead” or “Domain Owner” or “Strategic Facilitator,” which is corporate for “Greg, but with a better title.”
This person did fewer status meetings. They used AI tools. They moved faster. They also asked uncomfortable questions. They pushed for clarity. They noticed when things felt off. In other words, they did the parts of Greg’s job that mattered.
Chris relaxed for the first time in a long while.
“It felt like having direction again,” he said. “And it was nice just having someone asking me what I accomplished.”
“The new guy isn’t quite as good as Greg was, but he’ll get there. I hope.”
We are not witnessing the end of management. We are witnessing its reveal. All the parts that were once hidden inside meetings and org charts are being pulled into the light. Some will be automated. Some will be redesigned. Some will remain stubbornly human, and that’s as it should be.
If we’re careful, if we resist the urge to throw the whole thing out in a fit of efficiency, we might end up with something better. Fewer Gregs, perhaps. But the right parts of Greg, exactly where we need them.

