Would an AI Be a Better Boss Than Yours?

On managers, AI, and why we need to start asking harder questions

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Happy Tuesday,

January is off to a flying start. I’ve been running workshops back to back, and what’s exciting is how many AI agents are now actually live in organizations – not just pilots or experiments, but real solutions saving time and money. If you want help building something similar, reach out and let’s talk.

There’s a lot of leadership content coming your way this spring. It’s a topic close to my heart, and I think it’s time we have some honest conversations about what leadership actually means in the age of AI.

This article started as a simple question I’ve been asking audiences all fall. The reactions have been... interesting.

Let’s get to it.

You can also listen to the article on Spotify.

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I started many of my lectures during the fall with one simple question: Would an AI manager be better or worse than your current boss?

People squirm. There’s nervous laughter. (Especially when the boss is in the room.) Everyone’s first instinct is to shake their head. No way. An AI can’t be a better leader than a human. That’s just not possible.

But we need to sit with this question a bit longer and ponder it a bit more.

I’m not really asking whether AI should replace managers. I’m asking something more fundamental. What is a manager actually for? Why do we have them?
What’s the purpose?

Most people initially say managers exist to lead the work. To make sure things get done. And yes, that’s the basic function. We have hierarchies because we delegate. We have managers because someone needs to distribute tasks and ensure execution.

But what if that specific function could be done better by something else?

When you order food through DoorDash, no human is sitting there saying “Johannes is hungry, he wants a burger from Shake Shack, you’re the closest driver, go pick it up.” That’s already AI delegating work. Simple work, sure. But work delegation nonetheless.

Now, people push back. “But AI can’t feel empathy! It can’t understand people!”

Okay. But what is empathy, really? At its core, it’s about understanding someone’s context. Meeting them where they are. Being present with their struggles. And I’d argue that many GenAI models are quite empathetic in many interactions. Could we train AI systems to do this even better? I think we could.

Have you met managers who lack empathy? I certainly have. Throughout my career, I’ve encountered leaders who genuinely seemed to have no feel for people whatsoever. In some of those cases, and I mean this seriously, ChatGPT would have done a better job. Right now. Today.

That might be a wild thing to say. But I think it’s worth exercising the thought that AI could potentially do a better job than a human, even in what seems to be a very human-centric role, such as a manager.

We’re so locked into our human-centric view.
We assume humans are the ultimate solution for everything involving other humans. But are we? Are we really that much wiser than AI in every managerial dimension?

If we’re not, what does that mean?

With integrated data flows, with systems becoming more connected, with the ability to digitize almost every aspect of work, we could theoretically have AI orchestrating all task distribution across an entire organization. Whether you’re a plumber or a controller, most of what you do can be digitized to a large extent. We already have tools like Sana, Klang, and Granola capturing meetings for analysis. You could put cameras on workers to analyze their performance. You could use biometric data from an Oura Ring to understand stress and sleep patterns.

I know. Some of you are (rightfully?) thinking about surveillance and privacy. And those are legitimate concerns. But organizations exist to maximize returns for their owners. That’s what they do. If AI management achieves that more effectively, it will happen. Unless we have real conversations about it first.

And it doesn’t have to be dystopian. If your employer sees you slept badly or you’re stressed, maybe the response is more time off, not punishment.
It’s about what we decide to do with it.

The point is that the answer to “Would AI be a better boss?” isn’t as obvious as it used to be. A few years ago, I would have said AI couldn’t come close.
Now? I’m genuinely not sure.

Maybe we need to find new roles for human leaders. Maybe management shouldn’t be about work distribution anymore. Maybe it should focus on coaching, support, development. The traditional management role has its roots in military organization and the Industrial Revolution. Maybe it's time to challenge those old, sacred organizational structures.

Can we do this smarter? More effectively? I think we have to at least start asking, discussing and shape what the future of our leaders should be.

2026 seems like a good year to begin.

That’s my aspiration.