Employee Relations

How to Have a Difficult Conversation With an Employee

7 min read

Written by Charlotte, Founder & Principal HR Consultant

Almost every business owner we work with has the same story: something’s not quite right with an employee — timekeeping, attitude, the quality of their work — and instead of addressing it early, it gets put off. Not because it’s complicated, but because the conversation feels awkward, and small teams especially don’t want to damage what’s otherwise a good relationship.

The problem is that the issue rarely fixes itself. It usually gets worse, or it festers until you’re dealing with something much bigger than the original problem would have been. A short, honest conversation early is almost always easier than the alternative.

This isn’t a disciplinary process

Poor performance isn’t misconduct, so a disciplinary process isn’t the starting point when someone isn’t meeting the standard you need. Start by being clear about what isn’t working, listen to their side, provide any reasonable support or training they need, and set clear expectations for improvement.

If things don’t improve despite that, you may need to move into a more formal performance management process, which can ultimately lead to disciplinary action or dismissal in some circumstances.

The point of this conversation is to address the issue early — before it becomes a bigger problem. It’s about giving someone a fair opportunity to understand what’s not working and make a change.

Before the conversation

Get specific, not general

“Your attitude has been off lately” is hard to respond to and easy to disagree with. “You’ve been late three times this week, which means the rest of the team has had to cover the start of your shift” is specific, factual, and gives the employee something they can actually respond to. Where you can, explain the impact the behaviour or performance is having — on the team, customers, workload or business.

If the concern is about capability or performance, check the employee’s position description and any relevant expectations or previous discussions. Be clear about the gap between what is expected and what is actually happening. Consider whether there is training, coaching, additional support or clearer guidance that could reasonably help them meet the required standard.

Decide what you actually want to happen

Before you sit down, be clear in your own head what a good outcome looks like. Do you want the behaviour to stop? Do you need to see a particular standard of work? Do you need to understand what’s driving the issue first? Are you flagging a pattern before it becomes a bigger problem?

Be prepared to explain what needs to change, what good performance or behaviour looks like, and by when you expect to see improvement. Walking in without a clear sense of the outcome usually means the conversation drifts, and drifting conversations are the ones that feel awkward and achieve nothing.

Make it part of the regular conversation

If you already have regular one-to-ones with your employees, a concern doesn’t necessarily need to become a separate, formal-sounding meeting. Where appropriate, you can raise it as part of your normal one-to-one conversation: “I’ve noticed X — can we talk about what’s happening?”

This is one of the benefits of regular one-to-ones. They create a natural opportunity to give feedback, clarify expectations and address small issues before they become bigger ones.

If the issue is more serious, has been ongoing, or needs a more focused conversation, it may be appropriate to set aside a separate meeting. The important thing is not whether the conversation has a particular label, but that the employee understands the concern and has a fair opportunity to respond.

Pick a proper time and place

Not in front of other staff. Not five minutes before they’re due to clock off. Not as a drive-by comment while you’re both doing something else. Give the conversation enough time and privacy for the employee to respond properly.

If it is part of a regular one-to-one, you don’t need to over-formalise it. But make sure there is still enough time to have a genuine conversation rather than squeezing an important issue into the last two minutes of a meeting.

During the conversation

Say the actual thing, early

It’s easy to talk around a difficult issue because you don’t want to make the person uncomfortable. But too much explanation before getting to the point can make the conversation more awkward. Say clearly and calmly what the issue is, then give them the opportunity to respond. You don’t need to be harsh to be clear.

Then actually listen

Once you’ve raised it, stop and let them respond. There is very often context you don’t have — something going on outside work, a misunderstanding about expectations, a process issue that’s not really about them at all. This isn’t about giving them an opening to argue their way out of it. It’s that a conversation works better both ways, and you might genuinely learn something that changes how you handle it.

Agree on what happens next

End with clarity, not just an acknowledgement that the conversation happened. What specifically needs to change? By when? What does success look like, and what support will be provided?

Make sure the employee is clear about what you expect from them and what will happen next. This gives them a fair opportunity to make the necessary changes and gives you something clear to come back to in your next conversation.

After the conversation

Write down what was discussed and agreed, including the concern raised, the employee’s response, any support or training agreed, and what needs to change and by when. Then share a short summary with the employee so you both have a clear record of what was discussed and what is expected going forward.

This isn’t about building a case against someone. It’s about making sure there is no confusion later about what was discussed or what they were expected to do differently. It also gives the employee an opportunity to clarify anything they don’t think has been captured correctly.

Follow up as agreed. If you’ve set a timeframe for improvement, don’t wait until the end of that period to check in. Regular check-ins give you an opportunity to provide feedback, recognise progress and address any further concerns early.

If the issue doesn’t improve, you may need to move from an informal conversation towards a more formal performance management process. That’s a different, more procedural process, and it’s worth getting advice before you start it.

When to get advice first

Most day-to-day performance conversations don’t need outside input — you know your team and your business. It’s worth getting some advice first if the issue involves a health or personal matter, there has been a lot of history with the employee, or you think the situation could move towards a formal performance or disciplinary process. A quick conversation beforehand can help you approach it in the right way and avoid making things more complicated than they need to be.

Coaching managers through exactly this kind of conversation is a core part of our Manager support.

If you’ve got a conversation like this coming up and want to think it through first, get in touch. Talking it through beforehand, even briefly, tends to make these conversations go noticeably better.