How to Have a Difficult Conversation at Work (Prepare, Open, and Stay in It)

Somewhere on your list right now is a conversation you're avoiding. The team member who keeps turning up late. The colleague whose "jokes" stopped being funny a month ago. The employee doing solid work while quietly grinding everyone around them down.

You're not weak for putting it off. Most managers do. But avoidance has a cost, and it compounds. The problem keeps happening, your frustration builds, the rest of the team watches you not deal with it, and by the time you finally speak up, you're not having the small conversation you should have had six weeks ago. You're having a much bigger one, badly.

The good news is that this is a learnable skill, not a personality trait. The Fair Work Ombudsman's guidance for managers is built on a simple premise: many workplace issues can be sorted out early and informally by talking about them. And the best thinking on how to actually run that conversation comes from three Harvard Negotiation Project researchers whose work has held up for over 25 years.

Every difficult conversation is actually three conversations

In Difficult Conversations: How to Discuss What Matters Most, Douglas Stone, Bruce Patton and Sheila Heen argue that underneath every hard conversation, three separate conversations are running at once:

  • The "what happened?" conversation. The argument about facts, what they mean, and who's to blame. This is the one we think we're having.
  • The feelings conversation. What each person is feeling and whether those feelings are legitimate. Usually present, rarely spoken.
  • The identity conversation. The internal one. What does this situation say about me? Am I competent? Am I a good person? This is the conversation that makes your heart race before you knock on someone's door.

Most difficult conversations go wrong because we argue furiously in the first conversation while pretending the other two don't exist. The employee who gets defensive about a missed deadline usually isn't defending the deadline. They're defending their identity as someone who's good at their job.

Before you say a word: prepare

Preparation isn't rehearsing your opening speech. It's checking your own thinking, and Stone, Patton and Heen offer three shifts worth making before any hard conversation.

Shift from certainty to curiosity

You have a story about what happened. So do they, and theirs makes sense to them. Two people can agree completely on the facts and still disagree about what the facts mean. Walking in certain you're right guarantees an argument. Walking in curious about how they see it opens a conversation.

Don't confuse impact with intent

They hurt you, so they must have meant to. It's an almost automatic leap, and it's usually wrong. The authors' advice is blunt: you know the impact their behaviour had on you, but you're only guessing at their intent. Ask instead of assuming. And be ready for the reverse. Explaining that you meant well doesn't erase the impact you had on them.

Swap blame for contribution

Asking "whose fault is this?" shuts down learning, because everyone starts defending. Asking "what did we each contribute to this situation?" opens it up. Maybe they missed deadlines, and maybe you never made the deadlines clear, or made yourself so unapproachable that they couldn't flag the problem early. Contribution isn't the same as blame. Acknowledging yours doesn't let them off the hook. It makes it far more likely they'll acknowledge theirs.

One more preparation question matters: what's your purpose? The authors suggest three purposes that work: to learn their side, to express your view, and to solve the problem together. If your real purpose is to make them admit they're wrong, don't book the meeting. That conversation only ever goes one way.

Opening: start with the third story

Most conversations are lost in the first thirty seconds, because we open with our own version: "Your report was late again and it's not good enough." That's a verdict, and verdicts trigger defence.

Stone, Patton and Heen suggest opening instead with what they call the third story: the version a neutral observer would tell, one that describes the gap between your perspectives without judging either. Something like:

"I wanted to talk about the monthly report. I think we might see the deadlines differently, and I'd like to understand how it looks from your side and share how it's landing on mine."

Nobody has been accused of anything yet. You've named the issue, acknowledged there are two views, and invited them into a joint conversation rather than a trial.

Staying in it: the part nobody teaches

Opening well buys you five minutes. What happens next is where most managers come unstuck.

Listen like it's your job, because it is. The authors' single most useful rule: nothing productive happens until the other person believes you've understood them. When things get stuck, most of us push our point harder. Do the opposite. Ask an open question. Paraphrase what you've heard. If you're not sure what to do next, listen.

Acknowledge feelings without surrendering the issue. "I can see this has frustrated you" is not the same as "you're right." Feelings that get acknowledged tend to settle. Feelings that get dismissed leak back into the conversation as sarcasm, stonewalling or a formal complaint.

Watch your own identity wobble. If they say something that stings ("you play favourites"), your instinct is to fight the sting. Notice it instead. Managers who can own their mistakes and their share of the problem stay steadier under fire, and the conversation usually goes better because of it.

If it keeps derailing, name the dynamic. "I notice every time I raise the roster, we end up talking about the software instead. I'd like to come back to the roster." Saying the pattern out loud is often what finally breaks it.

And a point worth making from Fisher, Ury and Patton's Getting to Yes, the earlier Harvard Negotiation Project classic: be soft on the person and hard on the problem. You can hold a firm line on the work while staying respectful of the human doing it.

Know when it's no longer just a conversation

Everything above is for the informal, early conversation, which is where most issues should be resolved. But some conversations are the start of something formal, and the rules change when they are.

If the issue is ongoing underperformance, an informal chat that doesn't stick should lead into a proper process. We've covered that in our guide to managing underperformance under Fair Work.

If a conversation could realistically end in dismissal, procedural fairness starts to matter enormously. One example: the Fair Work Commission must consider any unreasonable refusal to allow a support person at discussions relating to dismissal when it decides whether a dismissal was unfair. Refusing that request in a heated moment can undermine an otherwise defensible decision.

And unresolved conflict isn't just uncomfortable. Safe Work Australia's model Code of Practice on managing psychosocial hazards recognises interpersonal conflict and poor workplace relationships as hazards employers have a duty to manage. We'll dig into that properly in a coming post.

The conversation you're avoiding is the one to have

Pick the conversation you've been putting off. Prepare using the three shifts. Open with the third story. Then stay in it, listening more than you talk. It won't be comfortable, but it will almost certainly be more comfortable than the formal process you'll face if you leave it another six months.

This article is general information, not legal advice. Every situation is different, so get advice on your specific circumstances where you need it.

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If a difficult conversation turns into a performance issue that needs structure behind it, our Performance Improvement Plan Template Pack gives you the documents to run that process properly. It won't have the conversation for you, but it will make sure what comes after is fair and defensible.