~Engineers solve problems, I solve engineer's problems 🤘
There’s no easy way to tell someone they’re leaving the team. Whether it’s the end of a probation period, a role that’s no longer needed, or a decision that things aren’t working out—this is one of those moments in management that nobody prepares you for, and it stays with you long after the conversation ends.
As a manager, you carry the weight of knowing you’re about to change someone’s life, their financial security, and potentially their confidence in ways that might take months or years to recover from.
Before you even schedule the meeting, you’ve likely spent weeks (or months) documenting concerns, having difficult conversations, providing feedback, and hoping things would turn around. You’ve probably lost sleep over it, questioned your own judgment, and wondered if you could have done more.
The truth is, if you’re a decent manager, you’ve already tried. You’ve given clear feedback, provided resources, adjusted expectations, and offered support. But sometimes, despite everyone’s best efforts, it just doesn’t work out. The role isn’t right, the skills gap is too wide, or the cultural fit isn’t there. And that’s okay—it doesn’t make you a bad person, and it doesn’t make them a bad person either.
There’s no way to sugarcoat this. Being vague or trying to soften the blow with corporate jargon only makes it worse. The person deserves clarity. They need to understand:
Before the meeting, make sure you have:
Don’t make them wait for details or chase you for information afterward. They’re already dealing with enough.
This conversation deserves privacy and respect. Not over Slack. Not in an open office. Not on a Friday afternoon when they’re about to go home for the weekend. Schedule it early in the week, in a private space, and give them time to process afterward.
Don’t build up to it with small talk or pleasantries. They’ll know something is wrong, and the anxiety will be unbearable. Start with something like:
“I asked you here today because I need to share a difficult decision. After careful consideration, we’ve decided that we need to part ways—your last day will be [date]. I want to talk you through what happens next and answer any questions you have.”
Then pause. Let them process. They might cry. They might get angry. They might go quiet. All of these reactions are valid. Give them space.
They deserve to know why. But frame it constructively:
Avoid personal attacks. Focus on the role fit, not their character. This isn’t about them being “bad”—it’s about the role not being right for them at this stage of their career.
After you’ve shared the decision, listen. They might have questions. They might want to understand what went wrong. They might need to express frustration or disappointment. Let them. This isn’t about defending your decision—it’s about giving them closure.
If you can, offer:
You don’t have to do this, but if you can, it helps. Remember, this person is about to go back into the job market. A little support can make a huge difference.
Send a follow-up email confirming:
This gives them something concrete to refer back to and ensures there’s no confusion.
This conversation will affect you too. You might feel guilty, sad, or relieved—all of these emotions are normal. Talk to someone you trust. Process what happened. Reflect on what you learned. And remember: making the right decision for the team and the company doesn’t make you a bad person.
Every difficult conversation is a learning opportunity. Ask yourself:
Use this to become a better manager. But don’t beat yourself up. Sometimes, despite everyone’s best efforts, things just don’t work out.
Over the years, I’ve learned a few things about these conversations:
It never gets easier. Anyone who tells you it does is lying or has become desensitized. If you’re human, telling someone they’re losing their job will always be hard.
Being kind doesn’t mean being weak. You can be direct, clear, and firm while still being empathetic. In fact, clarity is a form of kindness—it respects their intelligence and gives them what they need to move forward.
The way you handle this matters. Years later, people remember how you treated them during difficult times. Handle it with dignity and respect, and you’ll have no regrets.
It’s okay to feel conflicted. You can believe this is the right decision for the team while still feeling sad about it. These aren’t mutually exclusive emotions.
If you’re reading this and you’ve been on the receiving end of this conversation, I’m sorry. I know how much it hurts. But please know:
Managing people means making difficult decisions. Letting someone go is one of the hardest, but sometimes it’s necessary. When you have to do it, do it with clarity, kindness, and respect. Be human. Remember that on the other side of that conversation is a person with hopes, bills, and dreams—just like you.
And if you’re the one delivering this news, know that doing it well—with honesty, empathy, and dignity—is one of the most important things you’ll do as a manager. It won’t make it easy, but it will make it right.