Founder Fundamentals 5/10 – A Hard Choice

There are many hard choices as a founder. One of the hardest is choosing between being a CEO and being a person – a friend, a co-founder, the person people have gotten to know.

 It's a choice that can't be avoided. It surfaces when people and roles separate, which they inevitably do in a startup: roles change fast. People, not always.

Roles change particularly fast when a company finds product-market fit and starts to scale. At this point, a couple of things happen: a leadership layer forms between the founder and individual contributors - people who've never led must now lead. The founder's role shifts from expert to supervisor, requiring their direct reports to become a lot more autonomous. Specialisation sets in, hustlers need to become experts in a field. Things must now work repeatedly, not just once, and so process replaces improvisation, requiring different skills and thinking. And because there's more at stake now, the pressure and the speed of change increase on top of it all.

If a company cannot adapt to this change, it stalls. It needs its people to change. But what if people cannot do that, or at least not in time?

Most of them will have been here from the start. They were loyal. The company survived and got here because of them. Surely that counts for something?

From a human perspective: yes.

From a company perspective: no.

A company is only as good as it is competitive. If it's not competitive, it dies. And here's the thing: the past is irrelevant to competitiveness. Only the shape you're in now matters.

As CEO, your job is to keep the company in the best competitive shape possible. You must optimise for the present, not the past.

So when people can't change with their roles, you need to fill those roles with someone else - either letting them go or promoting someone above them. It can also mean that you and a co-founder will have to part ways. In any case, it means choosing the company over the people.

But leadership is about people. So how do you reconcile that? It's a fine line. You need to do what's best for the company with utmost integrity. Be honest, respectful, and reliable. Listen and act with empathy. But don't confuse integrity with doing what others wish you to do. It's not your job to be liked. It's not your job to create harmony or comfort.

What you do is dictated by your responsibility as a CEO. How you do it by your qualities as a person.

Here's what makes it even harder: it may not even be their fault. Maybe you didn't tell them clearly what was expected of them. Maybe they need more time. And most of the time, you won't be sure if your decision is right. It's a judgment call without counterfactuals. It may not feel fair to them. But fairness here isn't owed to one person. It's owed to everybody at the company, who deserve a company that's run to win.

It’s your job to see the whole picture. But not everybody will. And that can make you the face of hardship. You can explain your reasons - and you should - but ultimately that's yours to carry.

Just know this: your choice - it's ok. Your company needs you to take it.