The short answer
Pick one specific behavior, not their attitude. Tell them what you saw, what it caused, and what you need instead, by a date. Write it down the same day, in facts, and send them a short recap. Then follow through every single time it happens. If your boss or HR has protected this person before, agree the standard with your boss in writing before you act, so the decision isn't only yours.
First, name the kind of difficult
"Difficult" covers three different problems, and each one needs a different move.
Can't
They don't have the skill or the clarity. You see missed steps, slow work, confusion about what good looks like.
Move: make the standard explicit, show what done looks like, check in more often for a few weeks.
Won't
They know what's expected and do something else. You see ignored instructions, eye-rolling in meetings, going around you, the same excuse twice.
Move: a direct conversation about conduct, written down, with a clear consequence if it continues.
Protected
The behavior continues because someone above you lets it. They mention your boss's name when you push, past managers gave up, HR says "document it" and nothing happens.
Move: fix the agreement above you first. See section 5.
Most real cases are a mix. Start with whichever one is costing the team the most this week.
The first conversation, word for word
Do it in private, soon after something specific happens, and keep it short. Ten minutes is enough. Talk about one event, not their personality.
Open with what happened and what it caused
"I want to talk about Tuesday's client report. It went out two days late and without the numbers we agreed. That meant I had to apologise to the client and redo part of it. What happened?"
Then stop talking and listen. You're trying to learn whether this is can't, won't, or something going on in their life.
Set the standard and get a real yes
"Going forward, I need reports in by Monday 9am. If something's going to slip, tell me by Friday so we can plan around it. Can you do that?"
Wait for a yes or a specific objection. A shrug is not a yes.
If they blame other people
"Maybe other things played a part. I'm asking about your part, because that's the part you and I can fix."
If they say you're targeting them
"I hear that it feels that way. I'm talking about the report and the deadline, and I'd say the same to anyone on the team. What would make the expectation clearer?"
If they get upset
"Let's take ten minutes and come back to it. The expectation doesn't change, but I'd rather we talk when we can both think."
What to write down, the same day
A record isn't about building a case against someone. It protects you when your memory and theirs disagree, and it's the first thing HR will ask for.
- When: the date and time.
- What happened: in facts someone else could have observed.
- The impact: on clients, deadlines or the rest of the team.
- What was said: what you said and what they said, quoted where you can.
- What was agreed: the standard, and the date you'll check in.
Facts, not adjectives. "Arrived at 9:40 for a 9:00 meeting" holds up. "Was disrespectful again" doesn't.
Then send a short recap
"Thanks for talking today. To confirm what we agreed: reports in by Monday 9am, and a heads-up by Friday if anything will slip. Let's check in on the 24th."
Keep it neutral and short. If they push back on it in writing, that's useful too: now you know where you stand.
When it happens again
It usually does. What changes behavior is consistency, not how big the first conversation was.
"We agreed on Monday 9am, and this one came in Wednesday with no heads-up. This is the second time. I need to understand what's getting in the way, and I need you to know that if it happens again, it becomes a formal issue."
If you haven't told HR what's happening, tell them now. Formal steps such as a written warning or a performance improvement plan work differently from one company and country to the next, so follow your company's process and check with HR before you name one.
When your boss or HR won't back you
This is the part most advice skips, and it's often why the situation keeps coming back. The person may have history with your boss, a protector in leadership, or a reputation nobody wants to touch. If you act alone, it lands on you.
1. Get the standard agreed above you first
"Before I take this further with Jordan, I want us aligned on the standard: reports by Monday 9am, and a heads-up if one will slip. Is that how you see it?"
Then confirm it in one line by email afterwards. Silence becomes agreement, and now it's on record.
2. Make them own the decision
"If it happens again, what do you want me to do, and by when?"
Ask it once, then stop talking. Either they decide, or they've shown you they won't, which is also worth knowing.
3. Keep your record clean and boring
Dates, facts and what was agreed. Don't editorialise about your boss in it. If it's ever read by someone else, it should make you look careful, not angry.
4. Go to HR about policy, not frustration
"I want to make sure I'm handling this consistently with our policy. Here's what's happened and what's been agreed so far. What's the right next step?"
If none of this moves anything, that's a real answer about the job. It's worth deciding what you want before the next review, not after.
Mistakes that make it land on you
- Arguing about tone over email. Reply on facts, keep it short, and have the real conversation in person.
- Saving it up for the annual review. If they first hear about it there, it reads as an ambush, and the team will see it that way too.
- Feedback about attitude instead of behavior. "Be more positive" can't be measured. "If you disagree, say so in the meeting, not afterwards" can.
- Talking about them to the rest of the team. It always gets back.
- Skipping the record because this week was fine. Patterns only show up on paper.
- Going over your boss's head first. Ask your boss directly before you go around them.
A one-minute checklist
- I can describe the behavior without using adjectives.
- I've told them what I need instead, and by when.
- I wrote it down the same day and sent a recap.
- My boss has agreed the standard, in writing.
- I know what I'll do if it happens again.
Questions managers ask
Should I involve HR right away?
Tell HR early if the behavior involves safety, harassment, discrimination, or anything that could lead to a formal process. For everyday performance or conduct, have the first conversation yourself, write it down, and bring HR in when it happens again.
What if they're my best performer?
Talented people who make the team worse are still a cost. Name the specific behavior, and make it clear the standard applies to everyone. The rest of the team is watching how you handle it.
Can I just fire them?
That depends on your company's process, where you are, and the record you have. If firing is on the table, talk to HR before you say anything to the employee.
What if they used to be my peer?
Acknowledge it once ("I know this is a change for both of us"), then hold them to the same standard as anyone else. Being friendly isn't the same as being lenient.