“We need to talk…”: A leader’s guide to difficult conversations

Let’s be real for a second. Some conversations at work are a breeze. You dish out a “nice job!” or have a laugh with your team, and everyone walks away feeling good. But then there are those conversations — the ones that tie your stomach in knots just thinking about them. You know the ones: where someone’s behavior is off, or performance is slipping, and it falls to you — the leader — to say something.

Cue the internal panic.

If you’ve ever sat there hoping the issue would magically resolve itself while you quietly avoided eye contact with the problem, you’re not alone. Most leaders have been there. But here’s the not-so-fun truth: avoiding difficult conversations doesn’t make them disappear. It just gives them room to grow — and not in a good way. When small issues aren’t addressed, they can start to impact your team’s vibe, your credibility, and the trust people have in you.

So yes, you do need to say something. But the good news is, it doesn’t have to be terrifying — and you don’t need to do it perfectly to do it well.

First up — is this conversation even necessary?

Let’s start with knowing when a conversation is actually worth having.

Here’s your litmus test:

• Will this help the person grow?
• Will it improve the team dynamic?
• Will it build trust or clear the air?

If you can answer yes to any of those questions, then it’s worth leaning in — even if it’s awkward. And especially if it’s something that’s been quietly bugging you for a while. Chances are, it’s been bugging other people too.

Before you open your mouth — check your lens

We all come into conversations carrying our own thoughts, assumptions, emotions, and sometimes… a little baggage. Maybe you’re tired. Maybe you’re annoyed. Maybe you’ve already labelled the person as “difficult” before they’ve even said a word. It happens. But leadership starts with awareness.

So pause. And ask yourself these questions:

• Am I seeing this clearly — or through a fog of frustration?
• Have I already labelled this person as ‘difficult’?
• What else could be going on for them that I haven’t considered?

Then flip it.

• What might this situation look like from their perspective?
• Is there something going on that you haven’t considered?
• If a neutral third party was sitting in the room, how might they describe what’s happening?

That mental shift — seeing things from another angle — is called reframing. And it’s a leadership superpower. It creates room for empathy and understanding, even when things are uncomfortable.

A little prep - a lot less panic

Winging it might work for karaoke, but when it comes to tricky conversations it’s not your best move.

Even a dash of prep can make a huge difference. Before you dive in, ask yourself: What’s the point of this conversation?

• Are you trying to set clearer expectations?
• Nudge a change in behavior?
• Or maybe you’re genuinely curious about what’s going on for the person?

Clarity is your best friend here. Knowing your “why” helps you stay steady — even if the conversation takes a few unexpected turns.

And hey, not every moment gives you time to prep properly. Sometimes these tricky chats pop up mid-coffee or in a corridor. In those moments, hit pause (internally!) and do a lightning-fast reset: “What do I really want from this?”

That tiny question can turn a reactive response into an intentional one.

Because when you know where you’re heading, it’s a whole lot easier to steer the conversation — even if the road gets a little bumpy.

Go in with positive intent

Now, it’s time to lead with positive intent. That means assuming the other person isn’t trying to be difficult — in fact, they’re probably doing the best they can with what they know or have.

So instead of going into this conversation to criticise, you go in to support. You hold the mindset of: “I’m here because I believe in you, and I want to help you succeed.” That tone changes everything. It helps you stay curious, grounded in facts rather than feelings, and focused on a better future — not just what went wrong.

Words matter — a lot

And then, yes — it’s time to actually say the thing. A simple, genuine opener like, “Thanks for making time. I know this might feel a bit uncomfortable, but I want us to talk it through,” can go a long way. It tells the other person you’re not there to attack them — you’re there to have an honest, respectful chat.

Say what needs to be said, then pause. Yep, even if the silence feels awkward. This is about giving them time to take it in. And then … ask for their perspective:

• “How do you see this?”
• “Is there anything going on that I might not be aware of?”

Listen. Don’t jump in with rebuttals. Even if you hear something surprising or hard, stay curious. You might learn something that shifts how you see the situation entirely.

And if it veers off track? Gently steer it back by saying:

• “Let’s focus on finding a better way forward.”
• “We might not agree on everything, but I know we both care about getting this right.”

Think of yourself like a translator. Your job is to take a tricky or emotional topic and turn it into something constructive and clear.

• Be direct, not dramatic.
• Use “I” statements: “I’ve noticed…” or “I’m concerned about…”
• Be specific: “In yesterday’s meeting, you interrupted James several times.”
• Keep your tone calm and respectful — like you’re chatting over coffee, not delivering a courtroom verdict.

These approaches make it easier for your team member to hear you without getting defensive.

Stay flexible (because not all conversations go to plan)

And look — even with all the preparation and empathy in the world, some conversations still won’t go smoothly. Maybe emotions run high. Maybe the timing is off. Maybe the issue turns out to be more complicated than you thought. That’s okay.

If things start to spiral, you’re allowed to hit pause. It’s totally fine to say, “Let’s take a break and come back to this when we’ve both had a chance to reflect.” That’s not a failure. That’s smart leadership.

So, why does any of this matter?

At the end of the day, difficult conversations are part of the job — but they’re also a chance to lead with clarity, connection, and courage. Every time you show up and speak up, even when it’s hard, you’re building trust. And trust is the real secret sauce behind great teams and strong cultures.

So take a breath. Be brave. Start the conversation.

You’ve got this.

Want more tips like this? Check out our course Leading Difficult Conversations on RedSeed 1:1 — packed with practical ways to grow your confidence as a new leader.