How to have the hard conversation
you have been putting off.
It takes about fifteen minutes. You have probably spent longer than that this week thinking about not having it.
The short answer: decide the single thing you need to say and the single thing you are asking for, then open with it in the first thirty seconds. Give the specific evidence, stop and genuinely listen, state the expectation clearly, and agree a date to check. Write down what you both said afterward.
Almost all the pain lives in the run-up rather than the conversation. Managers rehearse a confrontation that, done properly, does not happen — the person usually already knows, and is often relieved someone finally said it out loud.
What waiting
is costing you.
Every week of delay makes the same conversation harder and less fair to the person on the other side of it.
Six months of nothing being said is six months of the person reasonably concluding it is fine. That is on the manager, not on them, and it will come up if this ever escalates.
Whatever it is, the people around it can see it. What they are actually watching is whether anything happens, and the answer sets the standard for everyone.
Managers who avoid the conversation do not stay neutral. They accumulate irritation, and it leaks into tone, opportunities and decisions the person cannot see or answer.
Most performance and behavior issues are correctable when raised early and plainly. Left long enough they become exits, which is a far worse outcome for everyone.
Prepare in ten minutes,
talk for fifteen.
Write Two Sentences Before You Walk In
One sentence for what the problem is. One for what you are asking them to do differently. If you cannot write the second sentence, you are not ready — you are frustrated, which is a different thing and it shows.
Bring two or three specific examples with dates. Not a pattern you have felt, instances you can name.
Open With It. No Warm-Up.
Do not ask about their weekend. The small talk does not soften anything, it just tells the person something bad is coming and makes them wait for it.
That is the whole opening. Problem, ask, and an open door, in about fifteen seconds.
Give the Evidence, Not the Character Assessment
Dates and specifics. Nobody can argue with what happened, and everybody can argue with what you concluded about them from it.
Then Actually Stop Talking
Ask what is going on and let the silence run. This is where you find out about the second job, the sick parent, the process change nobody told them about, or the fact that they have been carrying someone else’s work for a month.
You do not have to accept every explanation. You do have to hear it before you decide what happens next.
State the Expectation in Plain Numbers
Whatever you learned, end with something unambiguous. Vague expectations are the reason these conversations get repeated three times.
Say What Happens Next, Both Ways
Name the check-in date. If this is a serious or repeated issue, be straight about where it goes if nothing changes — not as a threat, as information they are entitled to have.
And say what you will do: the tool you will get them, the work you will take off, the person you will speak to.
Write It Down the Same Day
A short note to yourself, or an email to them summarizing what you agreed. Not to build a case — so that in six weeks you both remember the same conversation.
If this could ever become a formal process, check with HR early rather than late. That is a reason to start the conversation sooner, not a reason to delay it.
Four reactions
and what to do.
Handling the Moment
They get upset. Stop and let it happen. Do not fill it, do not retract what you said, and do not rush to reassure. Offer a few minutes or a reschedule for later the same day. Withdrawing the point because someone cried is what makes managers stop having these conversations at all.
They get angry. Lower your volume rather than matching theirs. If it stays heated, end it and reconvene the next day. Nothing useful gets decided by two people who are both defending themselves.
They flatly deny it. Go back to the specifics and stay there. If your facts are right, repeat them calmly and let the disagreement stand — you do not need them to agree, you need them to know the expectation.
They blame someone else. Take the part that is genuinely theirs and set the rest aside for you to look into. Then do look into it. A reason can be completely true and still not be the part they control.
Why this one
got so big.
Hard conversations are almost always a backlog of small ones that never happened. The manager who does four minutes of specific feedback in the week something occurs rarely needs the fifteen minute version at all.
Two habits prevent most of them: say the small thing while it is small, and be explicit about what good looks like before anyone falls short of it. Most underperformance is a standard nobody ever actually stated.
If it is the whole team rather than one person, the free workshop on giving and taking feedback resets it in an hour, and the accountability page covers the follow-up habit that keeps it from rebuilding.
You can protect your ego or you can improve your performance. You do not get both.
Common
questions.
How do you start a difficult conversation with an employee?
Open with it in the first thirty seconds rather than warming up. Name the problem, name what you are asking for, and add that you want to understand what is going on. Small talk beforehand does not soften it, it just makes the person wait for the bad news.
What do you say in a performance conversation?
Give two or three specific instances with dates rather than a characterization, ask what is going on and listen properly, then state the expectation in unambiguous terms and agree a date to review it.
What if the employee cries?
Stop and let it happen without filling the silence, retracting the point or rushing to reassure. Offer a few minutes or reconvene later the same day. Withdrawing the substance because someone became upset is what stops managers having these conversations at all.
Should you document a difficult conversation?
Yes, the same day. A short note or a summary email so both people remember the same conversation in six weeks. If it could become a formal process, involve HR early rather than late.
How long should the conversation take?
Around fifteen minutes, with about ten minutes of preparation. Longer usually means it has drifted into debating history rather than agreeing what changes next.
What happens if you keep avoiding it?
Silence reads as approval, so the behavior continues and becomes harder to raise fairly. The team notices nothing is being done and calibrates to that, and the manager accumulates resentment that leaks into decisions the person cannot see or answer.
Run it with your people.
The same ten concepts at five different levels of commitment. Every guide is written so the person running it takes part rather than instructs, and nothing is gated, licensed or paid.
The Lunch and Learn
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Open the Guide → 60 to 90 minutesThe Workshop
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One concept a week with real life in between. The version that changes how a group operates.
Open the Guide →Seventeen free guides for managers, sorted by the problem — first 90 days, feedback, hard conversations, retention, onboarding, meetings, retreats and change. Browse the guides, or pick the concepts your people need and get a session order back.
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Chris has taken this material onto morning television in seven markets, and writes for Forbes and Inc.
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