The first time I had to let someone go, I handled it so badly that thinking about it still makes me wince. Not cringe — wince. The physical kind, where your shoulders come up and your eyes close for half a second.
It was early in PipelineRoad’s life. We’d hired a content writer who seemed great in the interview. Articulate, enthusiastic, had a portfolio of decent B2B blog posts. Three months in, it was clear the fit was wrong. Not a bad person. Not even a bad writer. Just not what we needed, at the speed we needed it, with the level of ownership we required.
I knew by month two. I waited until month four to act. And when I finally did, I made every mistake in the book.
What I Got Wrong
I did it on a Friday afternoon. I’d read somewhere that Fridays were best because it gave the person the weekend to process. This is terrible advice. What it actually gives the person is two days of isolation, unable to talk to colleagues, unable to start job searching, unable to do anything but sit with the news and spiral.
I was vague about the reasons. I used phrases like “not the right fit” and “going in a different direction” because they felt kinder than specifics. They weren’t kinder. They were confusing. Without clear reasons, the person was left to fill in the blanks with their worst assumptions. Was it personal? Was it something they said? Was it their work? All of it? None of it?
I rushed through the conversation. The whole thing took maybe eight minutes. I had talking points on a piece of paper that I’d rehearsed in the shower that morning. I delivered them like a script. Asked if they had questions. They didn’t — because they were in shock. I took the silence as resolution. It wasn’t resolution. It was someone trying not to cry on a Zoom call with their boss.
And then I moved on with my day. Answered emails. Took another meeting. Told myself it went as well as it could have.
It did not go as well as it could have.
What It Actually Costs
Here’s what nobody prepares you for: firing someone doesn’t just affect the person you fire. It affects everyone.
The rest of the team notices. They notice how you do it, when you do it, and how you behave afterward. They’re watching to see if you’re the kind of leader who treats this as a necessary but painful act, or the kind who treats it as an inconvenience to get past.
After that first firing, the team was quiet for about a week. Not hostile. Just watchful. I later learned that two people had private conversations about whether they were next. Not because there was any indication they were — but because the way I’d handled it gave them no information to work with. They didn’t know why the person was let go. They didn’t know what the standards were. They just knew that someone could be here on Thursday and gone on Friday with no visible warning.
That silence taught me more about leadership than any book I’ve read. Your team doesn’t need you to be perfect. They need you to be legible. They need to understand the logic, even when they don’t like the outcome.
The Second Time
The second time I had to fire someone, about a year later, I did it differently. Not because I’d become enlightened, but because I’d been haunted by how badly the first time went.
The situation was similar — a hire who wasn’t meeting the standard, despite coaching and clear feedback over several weeks. The difference was everything leading up to the conversation.
This time, there were no surprises. I’d had three direct conversations over the preceding six weeks. Each one was specific: here’s what needs to improve, here’s the timeline, here’s what support is available. I documented everything — not for legal reasons, though that matters too, but because documentation forces clarity. When you have to write down “the problem is X, the expectation is Y, the gap is Z,” you can’t hide behind vague disappointment.
By the time we had the final conversation, the person knew it was coming. They’d seen the trajectory. Some of the shock was gone, replaced by something closer to resignation, which sounds worse but is actually more dignified. There’s a difference between being blindsided and being given every chance to succeed and still falling short.
I did it on a Tuesday morning. Not a Friday. Early in the day, so they had time to process while the world was still moving.
I was specific. “Here’s what we discussed on these dates. Here’s what needed to change. Here’s where we are. This isn’t working, and I’ve made the decision to part ways.”
I was direct, but I wasn’t cold. I told them I was sorry. Not the performative “I’m sorry but” that precedes a justification. Just: I’m sorry this didn’t work out. I mean that.
The conversation lasted about twenty-five minutes. They asked questions. Real questions, not stunned silence. What was the timeline? What about their projects? Could they tell the team themselves? Would I serve as a reference?
I had answers for all of it. Not because I’m some management prodigy, but because I’d spent the weekend thinking through every question they might ask and preparing honest responses.
The Principles I’ve Landed On
After several more of these conversations over the years — each one difficult, none of them easy — I’ve developed a set of principles that I try to follow. They’re not revolutionary. They’re just the result of getting it wrong and learning.
Speed matters, but not the way you think. Don’t rush the conversation. But don’t delay the decision. The longer you wait to fire someone you’ve decided to fire, the more you’re betraying both them and the team. Every week you delay is a week they could have been moving on. It’s also a week the team is carrying the weight of underperformance you haven’t addressed.
No surprises. If the termination is a surprise, you failed as a manager long before the conversation. Feedback should be continuous, specific, and documented. The firing should be the last step in a visible process, not the first time the person hears there’s a problem.
Be specific. “Not the right fit” is a coward’s explanation. The person deserves to know exactly why. Not to be cruel — but because specific feedback is useful. They can take it to their next role. They can grow from it. Vagueness helps nobody and protects only the person delivering the news.
Protect their dignity. This is the hardest one, because the logistics of termination are inherently undignifying. But small things matter. Let them tell the team if they want to. Don’t march them out immediately. Give them time to collect their things, transfer their work, say goodbye. Unless there’s a genuine security concern — which is rare — treat them like an adult.
Be generous where you can. Severance, if you can afford it. Extended benefits. A genuine offer to serve as a reference for the things they did well. Help with the job search if it’s appropriate. The cost to you is small. The impact on them is enormous.
Take care of the remaining team. After the person leaves, talk to the team. Not to gossip or explain private details, but to acknowledge what happened, explain the path forward, and give people space to ask questions. The team needs to see that this was handled thoughtfully, not capriciously.
The Aftermath
The part nobody talks about is what happens inside you.
I’ve fired people and then gone home and been terrible company for the evening. Quiet, distracted, running through the conversation in my head. Wondering if I said it right. Wondering if there was something I could have done differently three months ago that would have changed the outcome.
Sometimes the answer is yes. Sometimes you failed the person before the person failed the role. They were under-trained, or under-supported, or put in a position that didn’t match their strengths. Those are the firings that haunt you, because they’re partly your fault.
And you have to sit with that. You have to let the discomfort of it teach you something, so the next hire gets a better version of you as a manager.
The Reframe
I used to think of firing as the worst part of leadership. I still think it’s the hardest part. But I’ve stopped thinking of it as the worst part.
The worst part of leadership is avoiding the hard conversation. It’s keeping someone in a role they’re failing in because you’re too uncomfortable to act. It’s letting the whole team suffer because you don’t want to have a twenty-minute conversation that will hurt.
That avoidance masquerades as kindness. It’s not kindness. It’s cowardice dressed up as empathy. The kind thing — the genuinely kind thing — is to be honest, to be fast, and to do it well.
Because how you fire someone tells your team everything they need to know about who you are. Not the speeches. Not the all-hands meetings. Not the values on the wall. The firing. That’s the test.
And you don’t get to practice. Each one is live. Each one matters. Each one shapes the culture more than you realize.
I still wince thinking about that first time. But I’ve stopped trying to make the wince go away. It’s useful. It reminds me that this should never feel routine. The day it stops being hard is the day you’ve lost something you can’t afford to lose.