This newsletter is a hand-written reflection on an in-person conversation. You can watch the video or listen to the audio here.
Over a decade ago, one of my friends was an engineer at Etsy. He’s very talented, and they eventually moved him into a management position. I’ll never forget being surprised when he told me that, as a manager, he rarely wrote code, even though he was managing other engineers writing code.
At face value, it seems counter-intuitive that you can be good at managing people doing work that you aren’t doing, but management itself is a very difficult skill, and motivating a group of different people is arguably the hardest type of work.
But even though management is a skill, middle management earned a bad reputation because heavy organizational structure created an environment where unskilled people had authority over skilled people, which often led to an unhealthy imbalance.
That’s why Steve Jobs famously said that the best managers are individual contributors who don’t want to be managers.
Now, AI is forcing companies to take Jobs’ advice, and managers are expected to be player and coach.
The player/coach manager
The concept of a player/coach manager isn’t new. In the worst cases, people were ‘promoted’ into management positions while still being required to do their old job. In the best cases, a natural leader was identified and given more resources to continue leading.
In either case, the punchline is the same: as a player/coach you have to manage people and do the work of an individual contributor.
AI has entered the manager chat
AI is changing the way we work in two primary ways:
We can do new kinds of work
We can do more of the work we were already doing, faster
That means managers are now managing people with increased capacity, but more importantly, that they themselves are capable of more.
And ultimately, that means expectations for managers are changing.
Implicit and explicit expectations
As a manager, your boss’ expectations of you are changing because of AI, whether they’ve told you that or not, and in most cases, they probably haven’t, especially if they don’t have a good grasp of AI themselves.
That requires you to anticipate what they might want from you, or think they want from you. Increased output with the same resources? Higher quality work? Faster turnaround times? Better insights? A leaner team?
And, of course, the best course is always to try and make the implicit explicit, even if that means having a hard conversation.
How to manage well as a player/coach
The most difficult part of being a manager in the age of AI is that the technology itself, and the ways we use it, are changing incredibly fast. That means you need to be learning constantly, especially so you can teach your team, and you can’t rely on your past experience quite as much as you used to.
One of the most helpful things you can do is also one of the simplest: protect your calendar. The hours of experimentation have to come from somewhere, and you want that to be your choice, not someone else’s.
But the best advice is to have fun. You and your team can do so many things with AI, and as a manager, you often have the luxury of choosing the type of work you want to do.
So, reply no to those weekly update meetings that aren’t productive, fire up Claude, and build something that will make your next team meeting the best one you’ve had in a long time.
Watch or listen
You can watch or listen to the conversation that inspired this newsletter. Watch the video below, or check out the audio on Spotify or Apple Podcasts.