You know the conversation. Someone’s work has slipped, or the way they behave in meetings is causing problems, or a decision is about to land badly on them. You’ve known for a while. You’ve run it through in your head on the way home. You haven’t said anything yet.
That’s normal, and it’s also expensive. This page is about the preparation that makes the conversation easier to start and more likely to go somewhere useful.
Why do managers put off difficult conversations?
Because the cost of having the conversation is immediate, and the cost of avoiding it is spread out.
The CIPD’s Good Work Index 2024 asked UK workers who had experienced conflict at work how they responded. The most common answer was to let it go, at 47%. Only 17% had an informal discussion with the other person involved. Hemsley Fraser’s 2026 survey of L&D professionals describes leaders avoiding difficult conversations about performance because they lack the skills or tools to have them.
Avoiding it doesn’t keep things neutral. The rest of the team can usually see the problem, and they’re watching what you do about it. The accountability paradox explains why the conversation you’re not having is often the bigger risk to trust.
What should you decide before a difficult conversation?
Four things, written down, before you book it.
What is the one issue? Not the history of everything that has frustrated you. If there are three problems, choose the one that matters most, or the one the others hang from.
What do you actually know? Separate what happened from your reading of it. “Your last two client updates went out without the figures we agreed” is what happened. “You don’t care about this account” is a theory, and opening with a theory starts an argument about the theory.
What do you want to be different afterwards? Something they could do, by a date you could check. “Updates include the agreed figures, or you tell me by Wednesday if they won’t” is specific enough to agree to.
What’s yours to decide, and what isn’t? If you can offer support, flexibility or a change in workload, know that before you go in. If you can’t, don’t hint that you might.
This is one of the twenty behaviours that strengthen trust: Prepare before key interactions and decisions (9). It sounds obvious. Under pressure, it’s the first thing to go.
How do you rehearse what you’re going to say?
Rehearse the words, not just the points.
Most of us prepare a difficult conversation as a list of points and assume the words will come. Often they don’t. Under pressure we fall back on habit, and for many people that means softening the message until it disappears, or saying it more sharply than they meant to.
So write your first sentence down, word for word. Then say it out loud, on your own, a few times. You’ll hear straight away whether it sounds like you, whether it’s clear, and whether it carries an accusation you didn’t intend. Change it until it doesn’t.
Then rehearse what happens next. What are the two or three ways they’re most likely to respond? Upset, defensive, surprised, relieved? For each one, what’s your next sentence? You won’t follow a script, and you shouldn’t try to. The point is that when they push back, you’ve already heard yourself respond once.
Rehearse the quieter skills too: stopping after your first sentence and letting them answer, and checking what you heard before you reply. Those are hard to find in a tense moment if you’ve never practised them. Practise before it matters makes the case for trying them first in ordinary, low-stakes conversations, so they’re familiar by the time you need them.
There’s reasonable support for this. A meta-analysis by Driskell, Copper and Moran found that mental practice, rehearsing a task before you perform it, had a positive effect on performance, and that the effect depended on the type of task and on how long the gap was before the real thing. Most of those studies weren’t about conversations, so take the direction rather than the size, and rehearse close to the day. Acas’s guidance for managers on challenging conversations also suggests a pre-prepared script to help you stay on track, and treats role-play as a useful way to practise.
What should you say first?
The issue, plainly and early, followed by a question.
“Your last two client updates went out without the figures we agreed, and I’d like to understand what’s getting in the way.”
That opening does three things. It names the issue in plain words, so they aren’t left guessing why they’re there. It sticks to what happened. And it hands the conversation to them straight away.
Skip the long warm-up. Five minutes of small talk before the real subject usually makes the other person more anxious, not less, because they can tell something is coming.
How do you listen when it gets difficult?
Slow down at exactly the point you’ll want to speed up.
Three of the twenty behaviours carry most of the weight here:
- Listen and let others finish before responding (12).
- Ask questions and check your understanding before replying (13).
- Acknowledge how others feel before responding to the task (14).
Suppose your colleague says he’s been covering for someone on leave and didn’t mention it because he didn’t want to let anyone down. The conversation has just changed. If you respond to the task first (“the figures still matter”), you lose the most useful thing he’s told you. If you acknowledge it first (“that’s a lot to carry on your own”), then check (“so this started when you picked up her accounts?”), you can get to a workload problem you can actually do something about.
Underneath all of this is behaviour 16: Address issues directly with the person involved. The pattern that erodes trust is its opposite, talking about issues with others instead of the person involved. The person you’ve been avoiding is asking Do they believe I act with their interests in mind? Finding out that everyone else knew first answers that badly.
What happens after the conversation?
Write down what you agreed, share it, and book the follow-up before you leave the room.
Acas’s guidance makes the same point: document any agreement, give the employee a copy and arrange a follow-up meeting. The follow-up is where much of the trust is decided. If you said you’d look at their workload, look at it, and tell them what you found.
What should difficult conversations training include?
If you’re designing or buying training for difficult conversations, look for one thing above the rest: participants rehearsing their own real conversations, not invented case studies.
A meta-analysis of behaviour modelling training by Taylor, Russ-Eft and Chan found transfer to the job was greatest when, among other things, practice included scenarios the trainees generated themselves, trainees set goals, and their own managers were also trained. A conversation a manager actually has to hold next week is the most relevant scenario there is.
Then the practice has to carry on after the session. One real conversation, prepared, rehearsed and held, is worth more than a day of role-plays nobody uses. Which trust behaviours help with common leadership challenges? covers the conversation people keep putting off alongside six other challenges, with a first step for each.
Where this fits
In the Trust Leader Hub, a leader can choose one of these behaviours, such as addressing issues directly or acknowledging how others feel, and work through short activities that move from noticing it, to rehearsing it, to using it in a real conversation. Afterwards they record what happened, in their own words. See how a leader practises one behaviour.