If you’re a manager or business owner, you’ll eventually face it:

That conversation.

The one about performance slipping.
The one about behaviour that’s crossed a line.
The one you’d rather do just about anything else than have.

Here’s the thing. Avoiding these conversations doesn’t make the problem go away. It usually makes it worse. But done well, a difficult conversation can actually strengthen trust and improve performance.

This guide will walk you through five practical steps to handle difficult conversations at work with clarity, empathy, and confidence.

Step 1: Be clear on the purpose

Before you start, ask yourself: What is the main thing I need this person to understand or do after this conversation?

If you can’t answer that in one sentence, you’re not ready yet. Clarity is the foundation for a productive conversation.

Step 2: Prepare, but don’t script

Have your key points and real examples ready. Avoid memorising every word - you’ll sound robotic and leave no room for genuine dialogue.

Think about:

The facts (what happened, when, impact)
The behaviour or outcome you want to change
Any support or solutions you can offer

Step 3: Start with empathy, then move to facts

Begin on a human note. Acknowledge their contribution or effort, then address the specific behaviours or results that need to change.

Example:

“I really appreciate the extra hours you’ve been putting in lately. I wanted to chat because I’ve noticed deadlines have still been slipping, and I’d like to work out what’s getting in the way.”

Step 4: Keep it two-way

A conversation isn’t a lecture. Ask open questions. Listen to their perspective. You might uncover context you didn’t know, like a workload bottleneck or a process issue, before deciding on next steps.

Step 5: End with clarity

Ambiguity is the enemy here. Summarise what’s been agreed, outline next steps, and confirm any timelines. That way, both sides walk away knowing exactly what’s expected.

💡 Pro tip: The more you practise having small, honest conversations, the easier the big ones become.

Why leaders avoid these conversations (and why that’s a mistake)

Fear of damaging relationships
Worry about emotional reactions
Hoping the issue will “sort itself out”
Not knowing what to say or how to say it

Here’s the truth: Handled well, difficult conversations can actually improve trust.

People would rather have clarity and support than be left guessing about how they’re doing.

Want help with the words?

If you’ve ever thought, “I wish I knew exactly what to say in these moments”, I’ve got you covered.

The Manager’s Script Pack gives you ready-to-use conversation guides for the tricky situations leaders face most. Written in a human, practical tone that builds trust while getting results.

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The takeaway:

You can’t avoid difficult conversations forever, but you can approach them with clarity, empathy, and confidence. And the more prepared you are, the less daunting they’ll feel.

How to Have Difficult Conversations at Work (Without Losing Trust)