How to Handle Difficult Employees: Coach or Confront?

You have put the conversation off again.

You know one member of your team is affecting everyone else. Deadlines are slipping. Their attitude is becoming harder to ignore. Other people have started coming to you about it.

You keep hoping the situation will improve, because the alternative means sitting down and saying something that neither of you wants to hear.

If that sounds familiar, you are not alone. Even experienced leaders can hesitate when a conversation feels personal, unpredictable or likely to become emotional.

The question is rarely simply whether you should coach or confront them. The real question is: what is happening here, and what does good leadership require from you now?

Before you call someone difficult

If I had £1 for every time I had heard the words ‘difficult employee’, I would be sipping an Aperol on the Amalfi Coast rather than drinking Yorkshire Tea in my back garden.

I have used the label myself. It usually appears when someone is not behaving as we expect them to.

They may be missing deadlines, resisting feedback, questioning decisions, withdrawing from the team or bringing a negative tone into every meeting. The impact is real, but the label does not tell you why it is happening.

What looks like poor attitude could be confusion, fear, frustration or a loss of trust. Someone taking too long may be struggling with perfectionism. A colleague who seems defensive may have received vague or inconsistent feedback. A person who rarely contributes may need more time to process information before responding.

Curiosity does not mean making excuses. It means understanding the situation properly before deciding what to do.

Start with facts, not frustration

By the time a problem reaches you, you may already feel irritated. You have probably replayed several incidents in your head and formed a view about the person.

Before the conversation, separate what you know from what you think.

• What have you directly seen or heard?

• When did it happen?

• What was the effect on the work, the team or the customer?

• What expectation had already been made clear?

• What assumptions are you making about their motives?

‘You have a bad attitude’ gives the other person very little to work with.

‘The last three reports were submitted after the agreed deadline, which meant the wider team could not complete its work’ is specific. You can discuss it without turning the conversation into a judgement about their personality.

Is this a coaching conversation or an accountability conversation?

Coaching is useful when someone needs clarity, confidence, skill or the opportunity to think differently. You might ask what is getting in the way, what support they need and what they could do next.

Accountability is needed when expectations are clear, support has been offered and the behaviour continues. At that point, being endlessly curious can become another form of avoidance.

A useful way to decide is to ask:

• Do they understand what is expected?

• Do they have the skills, information and resources to do it?

• Have they had clear, specific feedback?

• Have I listened to their perspective?

• Has the impact of their behaviour been explained?

• Has anything changed since the last conversation?

If the answer to the first four questions is no, start with coaching. If those things have already happened and nothing is changing, you may need to be clearer about responsibility, standards and consequences.

Good leadership can be compassionate and firm at the same time.

Have the conversation before resentment takes over

The longer you wait, the harder it becomes to speak calmly. Small frustrations gather evidence until you find yourself confronting six months of behaviour in one uncomfortable meeting.

Start earlier and keep the opening simple.

You could say: ‘I want to talk about what I have noticed and understand what is happening from your point of view.’

Then explain the behaviour and its impact. Pause and listen. Their answer may give you important context, but it does not remove the need for a clear way forward.

Agree what needs to change, what support will be provided and when you will review progress. Do not leave with two different interpretations of what was decided.

What if the person reports to one of your managers?

At senior level, you may not be having every conversation yourself. Your job may be to help a manager stop avoiding it.

It is tempting to step in and solve the problem, particularly when the team is under pressure. That may bring short-term relief, but it can quietly undermine the manager and leave them no better equipped for the next situation.

Help them prepare. Ask what they have observed, what they need to say and what outcome they want. Challenge vague labels. Rehearse the opening with them. Then let them lead the conversation, with your support behind them.

You are developing the manager as well as addressing the problem.

Different does not automatically mean difficult

People do not all communicate, process information or respond to pressure in the same way.

Some are quick, direct and comfortable thinking out loud. Others are more cautious and need time to reflect. Neurodiversity, personality, experience and confidence can all affect how someone shows up at work.

This is why one leadership style will not bring out the best in everyone. You may need to change how you explain a task, give feedback or invite someone into a discussion.

Adapting your approach does not mean lowering the standard. It means giving people a fair chance to meet it.

So, should you coach or confront?

Begin with curiosity. Get specific about the behaviour. Listen properly. Offer the support that is genuinely needed.

Then be clear.

If someone can change and needs help to do it, coach them. If expectations have been understood and the behaviour continues, hold them accountable.

The kindest option is not always the easiest conversation. Sometimes the kindest thing you can do for the individual, the team and yourself is stop leaving the issue hanging in the air.

Help your managers handle difficult conversations

If your managers are avoiding people problems or relying on you to step in, Bold Moves for Teams gives them practical support to lead clearer conversations, understand different communication styles and deal with issues earlier.

Explore Bold Moves for Teams