Why do leaders keep the wrong employees in place?

Almost every leader I have ever worked with has an employee that they keep when they should either move their role or just let them go. They justify it by saying they don’t want to hurt them or that they are being loyal. There is a point, however, when you must remember you are running a business and that confronting the employee, kindly, is the best thing. Sometimes those conversations can help that employee open up and explain why they are struggling, and that allows room to actually help them with either therapy, coaching, skills training, or moving to a role that suits them better. However, aside from the employee’s experience here, there’s a bigger issue that leaders face around this topic, their own fear.

Many people hold on to the employee that doesn’t work because by being strong enough to have that difficult conversation or simply letting them go, they would have to face the uncomfortable facts that this shows about themselves. Maybe it’s our fear of being the bad guy, or the guilt when we recognise ourselves in them. Maybe it’s admitting that we have left them in place far too long or let them get away with poor behaviour. The biggest issue I work with clients on is simple: how to have and manage these conversations. Humans do not like conflict (surprisingly!). We are often scared that we will expose our own leadership blind spots. After all, who hired them, who kept them on…

Leaders often mistake empathy for tolerance, but true empathy is seeing someone clearly, both their strengths and their weaknesses. In my opinion, it’s helpful to help them work out where they thrive and where they just about survive. A simple conversation, role change or skills training can often help. Sometimes it’s addressing the limiting beliefs they have about themselves. You’re saying, I see you, I see you struggling, how can I help? Of course, there is also a time to say, this person isn’t taking responsibility for their actions and we run a business, they have to go.

Tolerance is different. It’s when we confuse kindness with avoidance, telling ourselves we’re being compassionate when really, we’re just postponing our own discomfort.

The truth is, keeping someone in a role that isn’t right for them is not kind, it’s unkind. They get stuck in a loop of underperformance, self-doubt and quiet shame. They get put on PDPs, which in all honesty make no one feel good. This keeps you trapped too, firefighting and making excuses for them while the team around them silently watches you tolerate what you say you don’t stand for…

I’ve worked with leaders who cry when they finally make that call. It is sad, and letting go of an employee is really hard, especially if they have been with you for a long time. This is why it’s crucial to learn to have those conversations quickly and directly when a problem starts to show. If you have tried everything to support them and they aren’t changing, then it’s time for a change.

Letting go is not about being ruthless. It’s about maturity. It’s recognising that leadership is not about rescuing people from their own path, but about creating clarity so they can walk it, even if that means walking away from you.

We hold on to the wrong people when we don’t trust ourselves. When we think “What if I can’t find someone better?” or “What if this causes chaos?” That voice is your own unhealed fear, fear of loss, failure, or being seen as unkind. But when you do the inner work to separate empathy from enmeshment, you start to lead from clean energy. Decisions become clearer. Conversations become calmer. You realise that the only way to truly honour someone is to stop holding them in a role that keeps both of you small

Letting go, in the end, is a love letter to growth, theirs and yours.