Wil Schroter
We have a great opportunity to be super tight with our employees — but should we be?
It's easy for us to fall in love with the idea of being close to the people we work with. In the early days of a startup, it’s almost unavoidable. We’re in the trenches together, working long hours, taking risks, and sharing wins. At some point, it stops feeling like a team and starts feeling like a family.
But there’s a line. And if we’re not careful, we cross it without realizing it. Suddenly we’re not just the boss. We’re the friend, the therapist, maybe even the surrogate parent. That closeness feels great, but it's also a potential liability.
I’ve been on both sides. I’ve run cultures where we were emotionally connected and others where we kept things professional. Both have their merits, but it's the "overly personal" side that I've seen create real dangers for Founders.
When things are going well, being close to your team feels like a strength. There’s trust, loyalty, and a shared sense of purpose. It feels good. It feels easy.
The problem isn’t how it works when everything is stable. The problem is what happens when it’s not.
When someone starts underperforming. When layoffs come up. When we need to give hard feedback. That closeness can cloud our judgment. We hesitate. We avoid. We let too much slide.
Reed Hastings, co-founder of Netflix, made a point of not calling his company a family. He called it a team. A family forgives almost anything. A high-performance team makes tough calls when it needs to. He was clear that emotional attachment can’t get in the way of the work.
It’s not that being close is wrong. It just doesn’t scale well when things get tough. And startups get tough all the time.
There's another side of this that is as easily overlooked; our team may not want to be that close to us. Frankly, we may be invading their worlds without even realizing it. I've been guilty of this countless times.
I (mistakenly) assumed that my staff would want me to help support their personal lives. I could help solve problems, give advice, or just be a shoulder to cry on. That's my default nature as an empath, but that doesn't mean the people I work with asked for it.
That relationship also works very differently for many people. A certain number of folks may have no interest in sharing, or being in an environment where that kind of openness exists. Some frankly hate it.
It's our job as Founders to start with that distinction. That not everyone wants in on the group hug. The default needs to be distance, with anything more only happening at an invitation to repeat.
It’s easy to confuse what we want with what’s appropriate. We want to feel connected. We want to be liked. We want to believe we’re building something deeper than just a business.
But even if friendship exists, we’re still the ones in charge. We’re the ones who decide who stays and who goes. That dynamic is never fully equal.
We can care about people without needing to be close. We can support them without being inside their lives. We can lead with empathy without needing emotional access.
It comes down to clarity. If we’re not clear, things get messy. When friendship gets in the way of hard decisions, the entire team feels it. When we overshare, the culture gets uncomfortable.
We can still celebrate birthdays. We can still ask how people are doing. But we need to remember that consistency and fairness matter more than friendship.
I’ve gotten this wrong more than once. I’ve let relationships get in the way of decisions. I’ve shared things I probably shouldn’t have. I’ve waited too long to act because I didn’t want to hurt someone I cared about.
That never worked out. It created confusion. It stalled progress. It made the team question what mattered more — performance or proximity.
The best leaders I know are approachable, but also structured. They show empathy, but they keep the line clear. They aren’t trying to be everyone’s best friend. They’re trying to lead well.
Being respected will always go further than being liked. Being trusted will always mean more than being personally close.
We don’t need to be our employees’ friends. We need to be consistent, fair, and human. That’s what makes us great to work with. And that’s what people will remember.
The Emotional Cost of Being a Founder When we talk about building startups, we talk about lots of costs: Staffing costs, the cost of capital, cost per acquisition, and opportunity cost. But we never talk about the biggest cost – the emotional cost.
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Why Money Can't Buy Happiness Being successful and having a lot of money doesn’t equate to genuine happiness. More often than not, it’s a fleeting distraction from other issues that require attention.
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