The Kindest Thing I Did Was Let Someone Go
I spent six months trying to make it work. Six months of coaching conversations, adjusted expectations, and "one more chance" discussions. Six months of convincing myself that if I just found the right approach, the right project, the right motivation - it would click.
It didn't click.
And honestly? I was doing more harm than good.
The Setup
They were a decent developer. Not terrible, not great. The kind of person who did fine when the work was interesting but disappeared when it wasn't. Who agreed to timelines in meetings but missed them without warning. Who had all the technical capability but none of the follow-through.
In another environment, maybe they would have thrived. A bigger company with more structure. A role with less autonomy. A team that didn't need everyone to be self-motivated.
But we were a startup. And startups are unforgiving environments for people who need external motivation.
The Mistake I Made
I kept trying to fix it. And by "it" I mean both sides:
Fixing them: More frequent check-ins. Clearer expectations. Explicit documentation of what success looked like. Performance improvement plans. Coaching. Feedback. More coaching. More feedback.
Fixing us: Maybe our processes were wrong. Maybe I wasn't communicating clearly enough. Maybe the projects weren't engaging. Maybe I was being too demanding.
The truth? Sometimes there's no process fix for a fundamental mismatch.
What I Told Myself
"They just need more time." "Maybe I'm not managing them correctly." "It would be cruel to let them go." "What if they improve next week?"
Meanwhile, the rest of my team was watching someone consistently not deliver while I gave them endless patience. They didn't say anything directly, but I could feel it. Why does mediocrity get infinite chances while we're busting our asses?
The Moment It Changed
It was during yet another 1:1 where we were discussing the same issues we'd discussed for months. I realized I was exhausted. Not from managing them - from pretending this was going to work.
They weren't happy. I could see it. They felt pressured, stressed, like they were constantly falling short. And they were right - because they were in an environment that didn't match their working style.
I was trying to change who they fundamentally were as a professional. And that's not management - that's fantasy.
The Conversation
I won't pretend it was easy. Letting someone go never is, even when it's the right call.
But here's what surprised me: the relief. Not just mine - theirs too.
When I finally said "I don't think this is the right fit," there was a moment of tension, then... acceptance. Maybe even relief that we could stop pretending this was working.
We talked honestly about mismatched expectations, different work styles, and how neither of us was wrong - just incompatible in this context.
What I Learned
1. "Culture fit" isn't code for discrimination - it's about compatible working styles
Some people thrive with autonomy. Others need structure. Some love moving fast and breaking things. Others need stability and predictability. None of these are wrong, but they're not all compatible.
2. Endless chances aren't kindness - they're avoidance
I thought I was being compassionate by giving more time, more coaching, more opportunities. Really, I was avoiding a hard decision. And in doing so, I was hurting them (constant feeling of failure), my team (watching inconsistent standards), and myself (exhausting emotional labor).
3. The right environment matters more than capability
They weren't a bad developer. They were a developer in the wrong environment. I'm convinced they're thriving somewhere with more structure, clearer boundaries, and less expectation to self-manage.
4. Your high performers are watching
Every day you tolerate low performance is a message to your high performers about what you actually value. Words are cheap. Standards enforced are what people believe.
5. Sometimes the kindest thing is letting go
Keeping someone in a role where they're constantly struggling isn't compassionate - it's cruel. Both to them (endless stress and feeling inadequate) and to you (emotional exhaustion).
The Aftermath
I let two people go within six months. Both times I agonized over the decision. Both times I questioned whether I'd done enough.
But you know what? The team's energy changed immediately. Not because people were happy someone was gone, but because standards became real again. Because it was clear that expectations weren't just suggestions.
And honestly? I think both people are better off. One found a role with more structure. The other realized startup life wasn't for them and moved to a larger company.
The Hard Truth
Not every management problem has a coaching solution.
Sometimes people are in the wrong role, wrong company, or wrong stage of their career for what you need. And that's okay. It doesn't make them bad. It doesn't make you a failure as a manager.
What makes you a failure is pretending it's working when it's not. Lying to them about their performance. Exhausting yourself trying to force compatibility that doesn't exist.
What I'd Do Differently
Move faster. I knew within three months it wasn't working. I spent three more months convincing myself I was wrong.
Be more direct. I softened feedback too much, hoping they'd read between the lines. They didn't. Explicit is kind.
Trust my instincts. My gut told me this wasn't going to work. My head convinced me to keep trying. My gut was right.
Set clearer expectations upfront. My Manager README came after these experiences. It should have come before.
The Bottom Line
Letting someone go doesn't mean you failed as a manager. Sometimes it means you succeeded at recognizing reality.
The goal isn't to keep everyone. It's to build a team that can actually deliver together.
And sometimes, the kindest thing you can do for someone is to release them to find an environment where they can actually succeed.
These are lessons from my own management journey. Your mileage may vary. But if you're exhausting yourself trying to make something work that fundamentally isn't - maybe it's time to ask whether "one more chance" is actually helping anyone.