Letting someone go

Letting someone go is perhaps the most difficult and most postponed management task. When there’s a growing mismatch, delaying the decision isn’t fair to anyone — but always let them leave through the front door.

You already know. That is the real problem. You have known for months — maybe longer. Deep down, in that honest place you visit at two in the morning, you know this is not working. And yet you have done nothing.

Key takeaways

• Every week you delay sends a silent signal to your best people that you will tolerate what they will not — and that costs you far more than any uncomfortable conversation.
• Letting someone go is almost never about the person being wrong or bad. It is about growing apart — a mismatch between what the role demands today and what the person brings. That distinction matters, and making peace with it is your job.
• The hardest part is not the conversation itself — it is the months of avoidance before it. Most leaders, looking back, regret waiting too long. Almost none regret acting too soon.

I have done this more than once in my corporate years. Each time was difficult. Each time was necessary. And each time, looking back with honesty, I had already known longer than I should have waited. The data was there. The conversations had been had. The gut feeling was unmistakable. But I kept finding reasons to wait one more quarter.

Sitting across from someone and telling them their time in this role is over is perhaps the hardest thing you will do as a leader. I have never met a leader who enjoys it. I have never met a good leader who avoids it.

Listen to the excuses you are making

I have heard every version of the delay. You probably recognise them too:

• Let us wait until the quarter is over.
• The timing is bad — there is too much going on right now.
• Let us give her an improvement plan first.
• We need to build a file. Document everything.
• Let us get her a coach. (This one is the worst. A coach is not a farewell gift.)

None of these are strategies. They are postponements. And postponement has a cost — paid by your best people, your organisation, and yes, by the person you are trying to spare.

5 signs you have already waited too long

• You find yourself mentally writing this person's performance review before they have had a chance to improve.
• Your strongest team members have stopped escalating issues to this person — they route around them without saying why.
• You have had the same conversation with them more than twice, and nothing has fundamentally changed.
• You feel a quiet sense of relief on the days they are absent.
• You are coaching yourself to be patient — when your gut stopped asking for patience six months ago.

If two or more of those are true, you are not protecting anyone. You are protecting yourself from an uncomfortable hour.

This is not about right or wrong

Here is what I have come to believe after doing this — and helping others through it — more times than I can count. The person is almost never wrong. They are not bad. They are not broken. What has happened, often gradually and without anyone meaning for it to, is that the role has grown faster than the person. Or the company has pivoted and the fit no longer holds. Or the chemistry with the team has frayed. This is about growing apart. No more. No less.

When you understand it that way, the conversation becomes different. You are not accusing. You are describing reality. And your job is to do that clearly, kindly, and without wavering.

The real cost of waiting

Your team knows. They have known longer than you have. Every week you delay, you are telling them — silently but unmistakably — that you will tolerate what they will not. That is leadership credibility you do not get back easily. The best people in your organisation are watching how you handle this. And they are making decisions about their own future based on what they see.

When you do it — do it right

Preparation matters enormously. This conversation should never be improvised, never be a surprise in a group setting, and never be rushed. Be clear. Be direct. Be human. Let them leave through the front door — with their dignity intact, their contributions genuinely acknowledged, and if appropriate, real support for what comes next. The decision must not waver. But how you execute it defines what kind of leader you are.

And make peace with your own emotions about it. The guilt you feel is not evidence that you are wrong. It is evidence that you are human. The two are not the same.

Often, a blessing in disguise

Let me tell you something I rarely say out loud. I was fired in my first job. I was twenty-six years old. It was my first real position, and they let me go. It hurt. Genuinely hurt. It made me insecure in ways I had not expected. I questioned myself for months.

But they were right. Looking back with clear eyes, it was a mismatch — between what the role required and what I was able to bring to it at that point in my life. It was not about being wrong or bad. It was about growing apart before we had even had the chance to grow together. They named it. I eventually did too.

That moment forced me to look in the mirror in a way I would not have chosen for myself. It forced me forward. It was, in the most real sense, a blessing in disguise. I would not be doing what I do today — working with leaders I respect on questions that matter — without that push at twenty-six.

So when you have that conversation, and you wonder what it will mean for the person sitting across from you: keep this in mind. The shock will pass. The freedom, eventually, arrives. And the path that opens on the other side of that door is often better than the one they were on. Your job is to open the door — with honesty, with respect, and without apology.

The future of your company depends on who stays — and just as much on who you have the courage to let go.

Over to you.

PS: Ask yourself honestly — in every case where you have let someone go, did you act too quickly? Or, looking back with clear eyes, did you already know, and wait longer than you needed to? I know what my answer is.