How to Start a Difficult Conversation at Work (With Examples)

You've noticed something at work that needs addressing.

Maybe a colleague keeps checking their phone while everyone else is busy. Perhaps an important task hasn't been completed, or someone's behaviour is starting to frustrate the team.

You know you should say something, but you're not quite sure how to start.

And then the questions begin.

What if they get defensive? What if I say the wrong thing? Is it even my place to bring this up?

So you put it off.

I've been on both sides of these conversations throughout my years in emergency nursing and leadership. And I've certainly got the opening wrong before.

I've walked into conversations with my own conclusions already formed, said them out loud, and created conflict that probably didn't need to happen.

Once I understood the other person's perspective, the situation sometimes looked completely different.

You don't need the perfect opening. You need one that gives you an opportunity to understand the situation before deciding what it means.

Here are some practical ways to do that.

Why Do We Avoid Difficult Conversations?

When preparing for my Human Skills workshops, one of the most common challenges people identify is knowing how to start a difficult conversation or give feedback.

They often know what needs addressing.

What worries them is how the other person might react.

Research by Adamska and Jurek into employee self-censorship identifies two reasons people may hold back from speaking up: fear of negative consequences and the belief that speaking up won't make a difference.

It's something I regularly see in workplace conversations.

People start creating a story about how someone will respond before they've even spoken to them.

“They’ll just get angry.”

“They never listen.”

“There’s no point bringing it up.”

But here's a question worth asking.

Is avoiding the conversation now creating a bigger problem later?

Not every issue needs a formal meeting or management involvement. Sometimes a respectful conversation is enough to clarify expectations or resolve a misunderstanding.

The challenge is getting started.

What to Say in the First Minute of a Difficult Conversation

You don't need a complicated script.

A useful opening has three parts.

1. Ask for the Conversation

Start with something simple.

“Can I check in with you about something?”

It's one of the phrases I regularly use.

It signals that there's something you want to discuss without immediately making an accusation.

2. Explain What You've Noticed

Stick to what you know rather than what you've assumed.

For example:

“The handover wasn’t completed before the shift ended.”

That's an observation.

“You never finish your work properly.”

That's a judgement.

A useful way to separate the two is to ask yourself what a camera would have recorded.

Describe the behaviour, not the story you've created about the person.

3. Ask a Genuine Question

Give the other person an opportunity to explain.

“Can you help me understand what happened?”

Then stop talking and listen.

Put those three steps together, and your opening might sound like this:

“Can I check in with you about something? I noticed the handover wasn’t completed before you left yesterday. Can you talk me through what happened?”

You've identified the issue without deciding why it happened.

None of these phrases guarantees a positive response, but they create an opportunity for a more constructive conversation.

Choose a suitable private moment where possible, explain why you’re raising the concern and allow time for the person to respond.

The Problem With Assuming You Know the Whole Story

Let's look at a common workplace example.

You've noticed a colleague checking their phone several times while everyone else is busy.

You're frustrated.

Eventually, someone says:

“You’re always on your phone. You need to stop.”

But what do we actually know?

We know they've been checking their phone.

We don't necessarily know why.

Perhaps they have a sick family member and are waiting for an update.

Maybe they don't understand the workplace expectations around personal phone use.

Perhaps they've developed the habit because nobody has addressed it before.

Or maybe they know the expectations perfectly well and are choosing to ignore them.

Same behaviour. Different explanations. Different conversations.

Instead of leading with an accusation, try:

“I’ve noticed you’ve been checking your phone a few times today. Can I check in with you about it?”

Then give them the opportunity to explain.

Depending on what you hear, the conversation might take a different direction.

If they're dealing with something personal:

“Thanks for letting me know. I’m sorry you’re dealing with that. Let’s work out how we can support you while still making sure the work is covered.”

If the expectations aren't clear:

“Thanks for explaining. The expectation here is that personal phone use doesn’t interfere with work. Let’s make sure we’re on the same page.”

If they understand the expectations but the behaviour continues:

“We’ve spoken about phone use before, and I’ve noticed it’s still happening. What needs to change so we can get this sorted?”

The final example is particularly relevant for managers and team leaders who need to reinforce expectations.

Understanding someone's perspective doesn't mean the behaviour can continue.

Curiosity isn't about letting people off the hook. It's about understanding the situation before deciding what needs to happen next.

Five Examples of How to Start a Difficult Conversation at Work

The same approach works across different workplace situations.

Here are five opening lines you can adapt.

1. When a task hasn't been completed

“Can I check in about the report that was due Friday? I noticed it hasn’t come through. Can you talk me through what’s happened?”

2. When someone's behaviour is affecting a meeting

“I noticed you interrupted Sam a couple of times during the meeting today. Can I get your perspective on how that discussion went?”

3. When you're giving feedback to a colleague

“Can I check something with you? I noticed something earlier, and I wanted to get your perspective before making any assumptions.”

4. When you need to raise an issue with your manager

“Can I get your thoughts on something? We’ve had a few late roster changes recently, and it’s making it difficult to plan ahead. Can we talk about how we might manage that?”

5. When you've been avoiding a conversation

“I probably should have raised this earlier. Can we talk about something that happened last week?”

You don't need to use these words exactly.

The important part is finding language that feels natural while keeping the conversation respectful and focused.

What if Someone Gets Defensive?

This is one of the biggest concerns I hear from managers and team leaders.

“I know exactly how they’re going to react.”

Maybe you do know how they've reacted in the past.

But that doesn't mean you know how this conversation will go.

You cannot control their response. You can influence how you approach them.

When someone becomes defensive, it's tempting to interrupt, correct them or defend your position.

Sometimes, a pause is more useful.

Give them space to explain. Listen for information you might have missed.

Research by Itzchakov and colleagues on high-quality listening during disagreements suggests that feeling genuinely heard can help people reflect less defensively.

That doesn't guarantee agreement, particularly in workplace feedback situations, but it reinforces the value of listening.

If the conversation moves away from the original concern, gently bring it back.

“I hear what you’re saying. Let’s come back to what happened today and work out what needs to happen next.”

You don't need to win the argument.

You need to understand the issue, clarify expectations and agree on a way forward.

When Should You Involve a Manager?

Not every workplace issue needs to land on a manager's desk.

In my Human Skills workshops, I use an activity called Direct, Check In or Escalate to help people consider the most appropriate response.

Direct:

When an issue is straightforward, low-risk and appropriate for you to address, have the conversation.

Check In:

When you're unsure what's happened or why someone's behaviour has changed, ask questions before making assumptions.

Escalate:

When an issue involves serious misconduct, bullying, harassment, discrimination, threats or safety concerns, use the appropriate workplace reporting process.

Escalation may also be necessary when expectations have been discussed, reasonable opportunities for improvement have been provided and the behaviour continues.

For serious concerns, a direct conversation may not be safe or appropriate. WorkSafe Victoria provides guidance on reporting workplace psychological health and safety concerns.

Curiosity isn't softness. And escalation isn't failure.

The skill is recognising which response the situation needs.

One Conversation to Try This Week

Think about a conversation you've been putting off.

It doesn't need to be a major workplace conflict.

Maybe it's a small behaviour that's frustrating you, an expectation that needs clarifying or something you've been meaning to address.

Before starting, ask yourself three questions:

• What do I actually know?
• What assumptions have I made?
• What question could help me understand their perspective?

Then start with something simple.

“Can I check in with you about something I’ve noticed?”

It might not go perfectly.

And that's okay.

These skills improve through practice, not by waiting until you feel completely confident.

You can't control how someone responds. But you can influence how the conversation begins.

Sometimes, the conversation you've been avoiding is the one that makes things better.

Make Human Skills Matter

If you're leading a team where difficult conversations keep getting put off, this is exactly the kind of practical skill I help people develop.

Through my Conversations That Actually Work workshop at Daniel Halls Co., teams practise giving feedback, handling difficult conversations and communicating clearly using realistic workplace situations.

Because knowing what good communication looks like is one thing.

Being able to use it when it matters is another.

Explore my workplace workshops or get in touch to discuss what your team needs.