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How to Have a Difficult Conversation With an Employee

November 02, 2026•7 min read

The conversation you’ve been avoiding since March is costing more than the conflict would.

To have a difficult conversation with an employee, use four moves in the same order every time: name the gap in observable facts, own your part, state the standard, and agree the next check. Most leaders don’t avoid these talks for lack of courage. They avoid them because they’ve rehearsed the argument and never written the first sentence.

You’ve had this conversation nine times. In the truck, in the shower, at 4 a.m. on a Thursday. You’ve won it every time.

You haven’t had it once with the other person in the room.

It’s on the calendar for Tuesday, and it’s been moved twice. You know what the problem is. You’ve got the examples, the dates, the two emails you forwarded to yourself. What you don’t have is the first sentence, and that’s the entire reason it’s still on the calendar.

You’re not short on conviction

Leaders who avoid hard conversations are almost never conflict-averse in general. You negotiate with suppliers. You’ve told a customer no. You’ve fired a vendor over a month-end invoice.

So the usual explanation, that you need to be more courageous, isn’t just unhelpful. It’s wrong. You’re plenty courageous. You’re unarmed.

Here’s what actually happens in the gap. You rehearse the case instead of the opening. You build the argument, which is the one part of the conversation that doesn’t need building, and you never write the twelve words that start it. So when Tuesday comes, you open with the weather, the project, and “how are things going generally,” and you hope she brings it up.

She doesn’t bring it up. People almost never volunteer their own shortfall to the person who signs their check.

Then one of two things happens. You soften it so far that she leaves the room believing it went well. That’s the worst outcome available, because now the clock resets and nothing changed. Or the conversation finally escapes under pressure six weeks later, hot, with an audience. And the version that comes out is three months of built-up frustration delivered as though it were about Thursday.

Count the cost of the delay honestly. The standard has been publicly optional since March. Everyone else noticed. Your best people are now watching to see whether the rule applies to anyone. And what makes good people leave isn’t conflict. It’s the discovery that nothing will change.

“The expensive conversation is not the hard one. It is the eleven easy ones you have instead, where you hint, and they nod, and you both leave thinking the other person understood something.”

— Josh Chumley, Co-Founder & CEO, XCL Group

How do you have hard conversations without losing the room?

Every hard conversation worth having has the same four moves in the same order. Learn the order once and you can build the words on the drive over.

1. Name the gap

One sentence. Observable facts, no adjectives, no story about motive. “The last three Monday reports came in Wednesday.” Not “you haven’t been prioritizing the reporting.”

The discipline is to say what a camera would have recorded. The moment you characterize the person instead of the behavior, you’ve handed them something to defend. And the rest of the hour goes to the defense.

2. Own your part

Second sentence, and it’s the one most leaders skip. “I noticed in March and I said nothing until today. That’s on me, and it made this harder for you.”

This isn’t softening, and it isn’t a negotiating concession. It’s accurate. A standard you didn’t enforce for four months wasn’t a standard. Saying so out loud is what makes the next move credible rather than arbitrary.

3. State the standard

Say the standard, not the feeling. Specific, measurable, dated. “Monday reports are in by 9 a.m. Monday. Starting this Monday.”

A conversation that ends in a mood instead of a standard will be repeated. If you can’t write the standard on an index card before you walk in, you’re not ready to have the conversation. You’re ready to complain.

4. Agree the next check

Put the follow-up on the calendar while you’re both still sitting down. “Let’s look at this again on the 29th, fifteen minutes.”

This move does more work than the other three combined. It turns a confrontation into a process, which lowers the temperature in the room right away. And it removes the question everyone leaves these meetings asking: did that count?

What does a difficult conversation with an employee sound like, start to finish?

A forty-person insurance agency. The sales manager, four years in and well liked, has missed his number three quarters running. He spends most of his week servicing his own book instead of coaching his five producers.

"Ryan, your team’s production is down eleven percent over three quarters, and your personal book is up. Last quarter you ran four of the twenty scheduled one-on-ones. (Gap.)

"I should have raised this in the second quarter. I didn’t, because you’re good and I didn’t want this conversation. That delay is mine. (Own.)

"The job is coaching five producers, not carrying your own book. Twenty one-on-ones a quarter, documented, and the team number owned by you. I’ll move eight of your accounts to free the hours. (Standard.)

“Fifteen minutes on the 29th, then monthly. (Check.)”

Four moves, under ninety seconds of actual content. Everything else in that meeting is Ryan talking, which is what you want.

Notice the agency owner handed over eight accounts in move three. A standard the person can’t physically meet isn’t a standard. It’s a trap with a date on it.

“Half the performance problems I get called into are not performance problems. The person was never told the standard in a sentence they could repeat. You cannot hold someone to a thing that only exists in your head.”

— Josh Chumley, Co-Founder & CEO, XCL Group

The tool: six scripts

The four moves are the structure. The scripts are the words, written out, for the six conversations that account for most of what leaders avoid:

  • Underperformance.
  • A missed commitment.
  • Attitude and tone. It’s the hardest to make observable, so the script gives you the camera-test language.
  • Peer conflict. Your job here is to be the referee, not the third party.
  • Letting someone go. Written for dignity and brevity, including the first forty seconds and what not to explain.
  • Apologizing well. The one most leaders have never seen modeled, where the whole weight sits in naming the cost to the other person rather than explaining your intent.

Each script runs one page: the opening sentence word for word, the four moves, two or three likely responses with what to say next, and a line for the standard and the check date.

Print the one you need. Fill in the standard before you walk in. Read the first sentence off the page if you have to. Nobody’s ever been offended by a leader who came prepared.

And if the conversation you keep avoiding is really about work that keeps bouncing back to your desk, our guide on how to delegate effectively covers the handoff side.

Frequently asked questions

How do you start a difficult conversation with an employee?

Open with one sentence of observable facts, the kind a camera would have recorded, like “The last three Monday reports came in Wednesday.” Skip the small talk and don’t describe the person’s motive.

What are the four moves of a hard conversation?

Name the gap, own your part, state the standard, and agree the next check. Use them in that order every time.

Why should a leader own their part in a hard conversation?

Because it’s accurate. A standard you didn’t enforce for months wasn’t really a standard, and saying so makes the new standard credible rather than arbitrary.

What happens if I keep postponing a hard conversation?

It doesn’t get easier. It gets larger, the standard becomes publicly optional, and your best people start watching to see whether the rule applies to anyone.

Tuesday

The conversation won’t get easier by being postponed. It gets larger. It starts to be about character instead of a report date, because that’s what happens to small problems left alone until they have company.

You already know what you need to say. What you’ve been missing is the first twelve words and the order of the rest. Write the gap in one sentence tonight, write the standard on an index card, and keep the appointment.

If you’d rather think it through with someone who’s had the conversation from both sides of the desk, that’s what the call is for.

Book a free Basecamp Call →

how to have a difficult conversation with an employee
blog author image

Josh Chumley

Josh is a bold, faith-first leader who has served in executive roles across the education, nonprofit, and ministry worlds. From leading a $30M P&L and managing 400+ staff, to raising millions in fundraising and mobilizing churches at the grassroots level, Josh brings unmatched energy and conviction to his work. He founded XCL to empower Christian leaders to lead with truth, strategy, and courage.

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