Difficult conversations at work: a manager's guide

Performance. The work is not good enough. The most common and the most fixable, and the one where evidence matters most.

Behaviour. How they treat people. Harder, because the person usually does not recognise the description, and because it requires you to talk about impact rather than intent.

Disappointment. They did not get the promotion, the project, the raise. You are not correcting anything; you are delivering a decision and protecting someone's motivation at the same time.

The sensitive one. Something personal is affecting work. Your job is to notice the effect, ask once, offer what you can, and not to diagnose anything.

Using the performance script for a behaviour conversation is the commonest mistake, and it is why so many of those go badly: you arrive with evidence for something the person experiences as a characterisation.

Seven steps. It takes twenty minutes.

1 — Name it, in the first thirty seconds. "I want to talk about the reporting deadlines." Not a warm-up. The person already knows something is coming and the preamble only raises their heart rate.

2 — Give the evidence, not the adjective. "The last three monthly packs were two, four and three days late" — not "you have been unreliable". Evidence can be discussed. An adjective can only be denied.

3 — Say the impact. What it caused, for whom. This is what turns a complaint into a reason.

4 — Stop talking. The step everyone skips and the one that determines the outcome. Ask "what is going on?" and then leave the silence alone, however long it gets.

5 — Listen to the account, and take it seriously. Perhaps a third of the time you will learn something that changes the conversation. If you do, say so.

6 — Agree what changes. Specific, and theirs where possible: "what would make this work?" beats a decree you have to police.

7 — Set the check-in. A date. Without it nothing happens, and you will be having this conversation again in six weeks with less credibility.

Steps 4 and 7 are the two that get dropped under pressure, and they are the two that make the difference between a conversation and a telling-off.

The sandwich. Praise, criticism, praise. Everybody knows the structure, so the praise is heard as the wrapper it is — which spends your real praise and buries the message. People genuinely leave sandwiched conversations believing they went well.

"Some people have said…" Never. Either you have observed it or you own the report. Anonymous evidence cannot be discussed, and it makes the person suspect their colleagues.

"I'm not saying you're lazy, but…" You just said it, and now you have said it dishonestly.

Doing it in writing. Email and messages remove tone, prevent the account, and end up forwarded. Write afterwards to confirm, never instead.

Doing it anywhere someone else can hear. Correction in front of others is remembered for years and is the fastest way to lose a team's trust.

Rehearsing until you are angry. Six weeks of imagined conversations make you arrive with a case rather than a question. Have the conversation earlier and you will not need the rehearsal.

Apologising for having it. "Sorry to do this" reframes a normal part of your job as an imposition, and it invites the other person to treat it as one.

Score before you book anything. 2 = yes, 1 = partly, 0 = no.

13–16: have it this week.

8–12: the gaps are named. Rows 2 and 5 are the usual ones and both are twenty minutes of preparation.

Below 8: you are not ready, and having it now will make the next one harder. Row 4 in particular — if nobody has ever told this person, your conversation is news rather than a correction, and that changes how you open.

Row 4 is checked less than any other and changes the most. Managers routinely deliver a "final" version of a message the person is hearing for the first time.

For one specific conversation. Fill it in longhand, the day before.

WHO: _________________________  WHEN: ____________________

THE ISSUE IN ONE SENTENCE, NO ADJECTIVES
______________________________________________________

MY EVIDENCE (dates, instances — at least two)
1. ___________________________________________________
2. ___________________________________________________
3. ___________________________________________________

THE IMPACT, AND ON WHOM
______________________________________________________

HAS ANYONE TOLD THEM THIS BEFORE?   Yes / No / I don't know

WHAT I WANT TO BE DIFFERENT, SPECIFICALLY
______________________________________________________

WHAT MIGHT THE EXPLANATION BE THAT I DO NOT KNOW?
______________________________________________________

MY OPENING SENTENCE, WORD FOR WORD
______________________________________________________

CHECK-IN DATE: ________________________________________

Copy the block — nothing to download and no email required.

Write the opening sentence word for word. It is the only part you need to get exactly right; everything after it is a conversation rather than a script.

Repeated lateness or slipping quality. "I want to talk about the last three deadlines. Two, four and three days late. Before I say anything else — what is going on?"

How they treat a colleague. "I want to talk about something that is about impact rather than intent. In Sunday's meeting, when you cut across [name] twice, the effect in the room was that she stopped contributing. I do not think you meant that. I do need it not to happen again."

A strong performer with a difficult manner. "Your work is genuinely excellent and that is not what this is about. The way you deal with the team is costing us things your work is earning us, and I want to be honest with you about that rather than keep working around it."

Someone whose work has dropped since something happened. "I have noticed the last few weeks have been different and I wanted to check in rather than assume. You do not have to tell me anything. If there is something I can do about workload or timing, I would rather know."

Telling someone they did not get it. "The decision went to [name], and I want to give you the real reason rather than a comfortable one."

Someone who disputes the facts. "We remember it differently, and I would rather establish what happened than argue about it. Can we go through the three instances one at a time?"

They cry. Stop, give it time, offer to continue later — and do continue later, because abandoning it teaches both of you that tears end conversations. "Take a minute. We can pick this up tomorrow if that is easier, but I do want us to finish it."

They get angry. Do not match it and do not retreat from the message. "I can see this has landed badly. I am not going to change what I said, but I do want to understand your side of it. Shall we keep going or take twenty minutes?"

They go silent. Let it sit longer than is comfortable. Then: "I would rather hear your view than guess it."

They dispute the facts. Go to the specific instances, one at a time. If they are right about one, say so immediately — it costs you nothing and buys the rest of the conversation.

They turn it on you. Sometimes fair. "That may be true and I will come back to it. I do not want to trade it against this, so let us finish this and then talk about that properly." Then actually do.

Write a short note the same day. Three or four lines: what you discussed, what was agreed, the check-in date. Not a warning, not a file note dressed up — a summary. It stops the two of you remembering different conversations.

Keep the check-in. A manager who has the hard conversation and never follows up has taught the team that the conversation was the consequence.

Treat them normally the next morning. Visible coldness afterwards is a second punishment and it is the part people remember.

If it becomes formal, follow your organisation's process. Where a matter may lead to a formal outcome, your HR process and the applicable rules govern it — find out what they are before you act, rather than after.

Privacy is not optional. A conversation held where anyone can hear changes from a correction into a public event, and the damage outlives the issue. Find a closed room, not a quiet corner.

Directness lands differently person by person, not by passport. Some people want it straight and some need it framed; you learn which by paying attention to the individual rather than by applying a rule to a group.

Use the language the person is most comfortable in for anything that matters. A hard message delivered in someone's second language is heard less accurately and remembered more harshly.

Avoid messaging apps for the message itself. They are normal for work here and they are the wrong channel for this; the message loses tone and gains permanence.

Mixed teams mean confirming what was heard. Ask them to say back what they understood the agreement to be. This is not condescending — it is how you find out that "I will look at it" meant something different to each of you.

Expect more indirect disagreement than open disagreement. Silence is not always agreement, which is why step 4 and the written summary both matter more here than a technique page would usually suggest.

How soon should I have it?

Within a week of noticing, and sooner if you can. Latency is the single biggest factor in how hard the conversation will be.

What if I am not sure it is a real problem?

Then ask before you tell. "I noticed X — help me understand it" is a legitimate conversation and it is often the whole intervention.

Should HR be there?

For most conversations, no — involving HR early changes an ordinary management conversation into a process. For anything that may have a formal outcome, or anything serious, find out your organisation's process first.

They report to someone else.

Then it is a conversation with their manager, not with them, unless the behaviour was directed at you.

I avoided this for six months and now it is worse.

Common. Open by naming your own delay — "I should have raised this months ago and I did not, which is on me" — and then have the conversation anyway. The acknowledgement costs you very little and removes their strongest objection.

What if they are more senior than me?

Same structure, shorter, and lead with evidence and impact rather than with what you want changed. And pick the moment rather than the corridor.

I keep having the same conversation with the same person.

Then the conversation is not the intervention any more. Two rounds with a check-in and no change means the next conversation is about consequences, and that is where your organisation's process comes in.

Write the issue in one sentence with no adjectives in it. Most managers discover that they cannot — and that is why the conversation has been postponed for two months, not because it is frightening.

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