Founder Fundamentals 7/10 – Your Worst Employee

I used to think the worst employee was the incompetent but likeable one. Not good on the job and slow to improve, but — being a genuinely nice, warm and sensitive person — not one to easily give candid feedback to or let go. I thought this was the person holding back a team the most. I was mistaken. The worst employee is competent: it's the problem solver gone bad.

Often this person is an early employee — operationally strong, a reliable deliverer of results, indispensable to a founder early on. Naturally, they get promoted, given more responsibility, handed bigger problems. And that's when things can take a bad turn.

It only takes two ingredients.

The first is character: everyone I've encountered here had a knack for hierarchy, not as a character flaw, just as a trait. I have yet to meet a strong team player gone bad.

The second is you. You keep reinforcing that this person's value lies in their ability to deliver answers and solve problems. You praise the output, not how they got there. You reward the hero, not the person who asked for help early enough to avoid needing one.

And so their identity fuses with having the answer. They can't not know. They can't not deliver. They can't be the person in the room who says: I'm stuck, I need help, I got this wrong.

This plays out everywhere, but the damage varies.

As long as the person remains an individual contributor, it's contained: a task they're too proud to ask for help on, a problem they try to solve alone until it blows up, a mistake they absorb rather than surface. Painful, but usually recoverable. And a good lesson — for both of you.

The real damage happens when this person moves into a leadership role — which, being your best problem solver, they almost inevitably do. Now the pattern scales. They keep doing what has worked so far: personally delivering results — and they extend it to their now-larger area of responsibility: owning every outcome and controlling every visible aspect of their realm. And because their identity is built around it, they resist anything that competes with it or makes it less necessary. It's self-reinforcing. And it quietly breaks three things: the people below them, cross-team collaboration, and transparency around mistakes.

Where are you in this? It depends:

If the leadership role you have given to a problem solver is recent (less than a year), and their team is still small (2–3 people) — great. Prevention is much easier than correction. Focus your praise on what their team achieves without them and on what their peers say about them. That's the signal you want to reinforce.

But if a problem solver has been leading an area for longer and something feels off — start searching. Talk to their people and to those who work across teams with them. Feedback may be fuzzy, particularly from their own team. Trust your instincts. The following are strong tells:

Start with their team. A strong leader makes their people more capable, more confident, more autonomous over time. With this person, the opposite is true. Their team doesn't move without them and has visible knowledge gaps only the problem solver can close. In meetings with you, team members are quiet and deferential — cautious, not confident. When you ask their team a question, the answer comes from them. They find a way to be in the room whenever you speak to their people.

Then look at what happens across teams. Other teams find collaboration with their area disproportionately difficult — requests get routed through them, responses slow down. In cross-functional settings, their people don't engage freely.

Last but not least, they are defensive about mistakes and will usually not admit them easily or proactively create transparency. When something goes wrong at the interface between teams, blame lands elsewhere quickly and precisely.

You will probably not be able to develop a definitive picture of what's going on. That's part of the problem. And this is why it's so important to trust your instincts. If you feel that things have taken a wrong turn, make a conscious decision to act and be prepared to dig deep. If the pattern has been running for a while, addressing the behaviour alone won't be enough. Assume there are already problems sitting in a closet — mistakes absorbed rather than surfaced, team members afraid and unmotivated, and collaboration quietly broken down or bypassed.

The corrective work runs on two tracks. The first is conversational: review regularly what is not going well, encourage openness, and don't criticise what surfaces. Ask them to name the high performers in their team and review those people's development together. The second is structural: create direct lines of communication across teams, make collaboration an explicit item in your feedback processes, and make it standard for teams to present their own work and for your access to people not to be mediated. On all of this, expect pushback — including it becoming personal (my people are afraid to talk to you; if you force me to work this way, we will not achieve our goals; you don't trust me, I'm hurt!). Don't let that slow you down. Make it clear that this matters to you.

Your best early employee can become your worst structural problem. Not because they changed, but because you kept rewarding what got you here instead of what gets you there.