Deep down, most founders think they’re pretty ordinary at managing people.
Not all of them are right about that, but a significant number are a little bit shit at it. It’s not all that surprising, given the type of person who decides to become a founder …
A typically successful founder is high-agency, strong in vision, immensely self-believing, resistant to being told what to do, irrationally optimistic, action-oriented, and with a low tolerance for mediocrity.
It turns out those traits make you excellent at starting companies, and fairly average at managing people.
What’s strange is that nobody seems to find this alarming.
We spend enormous energy helping founders get better at fundraising, GTM, and product. And yet people management gets almost no formal attention.
Instead, we rely on osmosis. We watch how previous managers behaved and copy what we liked, while avoiding what we didn’t. We march on in the vague hope that it will sort itself out.
It rarely does.
The thing founders actually enjoy
When I hear a founder say how much they enjoy working with someone, it almost always means one thing: that person requires almost no management. They’re a high-agency operator who runs hard at a problem and comes back with results.
They need nothing more than a vaguely worded statement about what you’d like to happen and a wave of the arm—and off they go. The next time you hear from them, they’ve already completed the task, solved four other problems you didn’t know existed, and are back asking for something more challenging.
Those people are great, but managing them isn’t really management. It’s more like hanging out with people you like.
The real test of your management capability shows up with everyone else – the person who’s talented but needs more direction than you’d prefer to give. The one whose communication style grates on you.
Your patience runs out with these people, and often you’ve decided they’re incompetent. But in reality, they may actually be good at their job with the right kind of management. You just have to decide whether you are actually willing to be their manager.
Management as leverage
Once you hit a team of around 15 to 20 people, you’ve probably stopped being an individual contributor (IC). You are no longer the one shipping the work. You are the one who determines whether the people shipping the work can do it well, with clarity, in an environment that brings out their best.
That’s the job now. And it’s one of the highest leverage activities available to you as a founder.
Think about it this way. If you make yourself 20% better at your craft as an IC, the output improvement is linear. It flows through you. If you make yourself 20% better at developing and leading the people around you, that improvement multiplies across every person you manage, and every person they manage.
Most founders understand this intellectually, but they revert back to doing the thing they’re comfortable with. Because managing people is uncomfortable, and coding or selling or building product is not.
Why we don’t try to get better at it
I suspect the reason founders don’t invest in improving as managers is not complicated. They don’t enjoy it, and they’ve made a quiet deal with themselves that trying to get better at it will just create more of the thing they don’t want to do.
There’s also a fantasy version of the business that lives in the back of every founder’s mind. The one where all they need to do is hire great people, and they will execute flawlessly without any input from the founder. No difficult conversations. No performance management. No one crying in the car park.
I understand the fantasy. It’s just not real though.
If you want to operate at the C-suite level, then managing people is not adjacent to the job. It is the job. And if you’ve decided you genuinely hate it and can’t be moved on the subject, then you should think hard about whether an IC role inside the business is a better fit for you? That’s a legitimate career path.
What actually helps
If you’ve willing to admit that people management is a gap, here’s where I’d start.
- Read the classics. Management has decades of rigorous thinking behind it that gets routinely ignored in favour of whatever a famous CEO said on a podcast last week. Andy Grove’s High Output Management remains one of the best books ever written on the subject. It was published in 1983 and it has aged almost perfectly. Start there.
- Ignore the fads. Jensen Huang runs Nvidia with no one-on-ones, preferring instead to tackle issues with his entire leadership group at once, and has made it work spectacularly. It is also, for almost everyone who is not Jensen Huang, genuinely terrible advice. The fact that it works for one of the most exceptional operators in the history of the technology industry does not make it a template. Copy the principles behind great management, not the weird habits of outliers.
- Work out what specifically you don’t like. Is it the difficult conversations? Tolerating underperformance for too long because the thought of addressing it is exhausting? Drawing the line between what’s your problem to solve and what needs to be pushed back down? These are all learnable. But you have to name the thing before you can work on it.
- Fire faster. I say this gently, but I do mean it. A huge proportion of the misery that founders associate with people management comes from tolerating behaviour or performance that should have been addressed months earlier. The longer it runs, the harder everything gets. Everyone is waiting for you to do the thing you keep not doing. Getting better at this removes a lot of management dread.
Most founders started out as individual contributors. They were good at a specific skill, they started a company, and somewhere along the way the job changed completely beneath them. No one handed them a manual.
But you can get better at anything if you choose to work on it.
