When to Let Someone Go — And Why You've Already Waited Too Long

The conversation you are not having

In most businesses above a certain size there is at least one person who should not be in their current role. Not a bad person. Often a good person, with real loyalty, genuine effort, and a history with the business. But someone who is in the wrong role, or at the wrong level, or simply not the right fit for where the business is going.

And the owner knows it. Has known it for longer than they would comfortably admit. Has been working around it, compensating for it, having the gentle version of the conversation and hoping it will be enough. It usually is not.

One of the most reliably costly decisions in a growing business is not the decision to let someone go. It is the ongoing decision to keep not making it.

Why owners wait

The reasons are understandable even if the result is not.

Loyalty is real. In small and growing businesses, people are not just employees. They were there when things were hard. They held things together in difficult periods. Letting them go feels like a betrayal of that history regardless of the current situation.

Conflict avoidance is real. The conversation is uncomfortable. The person might be upset or feel blindsided. The aftermath in the team is unpredictable. It is easier to keep managing around the problem than to have the conversation that ends it.

Hope is real. People do change. Performance does improve. The next quarter might be different. The version of optimism that keeps a business owner going through difficult periods can also keep an underperforming situation going well past its useful life.

And underneath all of these, sometimes, is a harder truth. The owner is not sure the problem is the person. They wonder whether, with better systems or better management, the situation would look different. That uncertainty is worth taking seriously. It is also worth resolving rather than using as a reason to defer the decision indefinitely.

What waiting actually costs

The cost of keeping the wrong person in the wrong role is almost always higher than it appears from inside the situation.

There is the direct performance cost. The work not being done to the standard it needs, the decisions not being made, the opportunities not being taken. This is measurable if you are honest about measuring it.

There is the team cost, and this one is usually underestimated. High-performing people notice. They notice who is being held to account and who is not. They notice the owner working around a problem that should be solved. And they draw conclusions about whether this is a place where performance genuinely matters. The best people in your team are watching what you do with the weakest.

There is the management cost. The hours spent compensating, coaching, worrying, and waiting for improvement. Those hours have an opportunity cost that rarely gets acknowledged.

And there is the personal cost to the owner. The low-level drain of a situation you know needs resolving but keeps not being resolved. It creates a background noise of unfinished business that is more exhausting than the conversation itself.

Performance problem or fit problem

Before having the conversation it is worth being clear about what you are actually dealing with.

A performance problem has a specific and observable gap between what the role requires and what the person is delivering. It can be named, measured, and addressed. Sometimes it is a capability issue. Sometimes it is a resource issue. Sometimes, honestly, it is a management issue, and the person has not been given what they need to succeed. If that is the case it is worth addressing before drawing conclusions.

A fit problem is different. The person is capable and trying but is simply not right for where the business is going. The skills that were valuable twelve months ago are not the skills the business needs now. The culture has shifted and they have not moved with it. The role has grown and they have not grown with it. These situations are often the hardest because there is nothing wrong with the person and yet the situation is still wrong.

Patrick Lencioni's framework is useful here. The ideal team member is hungry, humble, and people smart. Someone who is consistently missing one of those qualities, despite genuine effort to address it, is probably not going to change. The kindest thing for them as well as for the business is clarity rather than prolonged ambiguity.

How to handle it well

Dignity and directness are not in conflict. The conversation can be honest, clear, and respectful at the same time. The worst versions of these conversations are the ones where the owner has been so indirect for so long that the person is genuinely surprised. That is not kindness. It is conflict avoidance dressed up as consideration.

The person deserves honesty. They deserve to know specifically what is not working and why. They deserve to be treated as an adult who can handle a difficult truth, even if that truth is that the business has moved on and the role they are in is no longer right for them.

Jim Collins put it plainly. If you know you need to make a people change, the time to make it is now. The longer you wait, the more it costs everyone involved.

Building the right team is the most important thing you will do.

Book a free Scale & Exit Diagnostic. We will look honestly at your team structure, where the gaps are, and what needs to change to give the business the foundation it needs to grow. Book your diagnostic at simonellson.com or call 01305 566250.