I walked into many difficult conversations over almost two decades of managing teams. Sometimes the conversation ended up going great, and we made great progress. Other times it went, pardon my French, tits up and we both left the room confused, frustrated, and wondering what went wrong.
Now, let’s be clear: a difficult conversation is, well, difficult. Kind of comes with the name. It’s not going to be easy sailing, but it sometimes needs to be done.
That said, you might as well maximise your chances of success.
There are many situations where you’ll have difficult conversations, but in my experience the most common type is the “performance issue” one.
So let’s talk about that, because I have views.
Actually Delivering the Feedback
First, let’s cover what to actually say, because that’s how you start the meeting.
The biggest mistake you can do is to be vague. Managers say things like “you need to improve the quality of your work” or “you need to be more proactive.”
That’s useless.
The assumption here is that we’re all trying to do the right thing. If your person is instead actually trying to knowingly damage your company or organisation, that’s a very different situation.
But to help them understand that what they’re doing is not actually working, you need to be specific. Painfully specific.
Focus on facts, and give examples. Facts and examples are amazing: you can’t really argue with them. Duh.
That is easier said than done: many times, I heard managers argue that “it’s a fact that they’re not motivated”, or “they clearly don’t care about quality”.
Pop quiz: are those facts or not? Spoilers: they might be motivated but overwhelmed, for example, or really care about quality but struggling to learn how to trade off quality with speed. Or something completely different. The fact (yeah, pun intended) is that you don’t know. So, nope. Not facts.
Instead of “You don’t seem to care about quality”, you could say “the quality of your code doesn’t meet the bar we are looking for”. That’s a fact. See what I did there?
You also need examples.
That’s kind of hard work, so many managers don’t look for examples. Don’t be those managers. Take notes day to day, so you have your examples ready when you need them.
That way, you can add something like “in the last three pull requests, you’ve had an average of 12 comments per review about missing error handling and unclear variable names. That’s significantly higher than the team average of 3-4 comments.”
The specificity serves two purposes. First, as we said, they can’t argue with facts. “You need to be better” is debatable. “You missed three deadlines in the last month” is not. Second, it shows you’re paying attention. Vague feedback feels like you’re going through the motions. Specific feedback shows you actually know what’s happening.
What not to do!
Whatever you do, don’t use the shit sandwich. You know, “you’re great at X, but you need to work on Y, and also you’re great at Z.” It’s super cringe. It makes the positive feedback fake and hides the critical feedback, and it confuses the message. You can’t fault them for wondering if they’re doing ok (two goods one bad is not that bad, right?) or not.
Just say the thing you need to say.
“I need to talk to you about your performance. Here’s what I’m seeing, here’s why it’s a problem, and we need to fix it.”
The Three Breakdown Moments
Now for the part most managers aren’t prepared for: the three common moments where performance conversations fall apart.
1. Managing the Defensive Reaction
You delivered the feedback, life is good. A weight has been pulled from your chest. For sure they’ll appreciate your honesty and your willingness to work shit out with them, right?
Wrong. Often, they get defensive, shut down completely, or start making excuses.
That’s normal: they’re feeling under attack and they’re responding with some variant of flight, fight or freeze response.
Your instinct might be to engage with that. When they attack, you defend your position. When they make excuses, you argue back. When they go silent, you fill the void with more talking.
Don’t do that. Here’s what to do instead.
When they fight back
Acknowledge what they’re feeling, but don’t argue with it.
Say “I can see you’re frustrated” or “I know this is hard to hear.” Then return to the facts. Say, “Here’s what I observed” and repeat the specific examples. Don’t get pulled into defending yourself or debating whether your perception is valid. After all, we already established that facts are facts.
When they freeze
Let the silence sit.
Count to ten in your head if you need to. They’re processing, and that’s okay.
If they still stay quiet, you can ask at that point: “What’s on your mind?” But resist the urge to fill the silence with explanations or backtracking. Silence feels uncomfortable, but it’s productive.
When they make excuses
You need to make sure you distinguish between excuses and context. “The requirements kept changing” might be a legitimate factor or it might be deflection.
Listen, then redirect: “I hear that the requirements changed twice. And you still missed the deadline by two weeks. How do you think we can handle changing requirements differently next time?”
Again, keep it as collaborative as possible: their justification might be valid, but the outcome still needs to change. It might not have been their fault, but it’s still their problem.
2. The Ownership Problem
It might or might not have happened, that at times I walked in with the whole thing figured out for them. Here’s the goals, here’s the activities you need to do, here’s the support you’ll get.
Here’s a secret for you: you can’t own their improvement.
Here’s what I see happening when you prescribe the solution: they nod along, agree to everything, and then… nothing improves. And once nothing improves, it is suddenly your failure too. Why? Because they didn’t own it. They were just doing as told and you told them what to do, so now it’s your plan, not theirs.
Instead, bring them into the conversation as active parts. After you’ve delivered the feedback and navigated their defensive reaction, it’s time to collaborate.
“What do you think needs to happen here?” “How do you think we can fix this?” “What would success look like from your perspective?”
This does two things. First, it tells you if they actually understand the problem. If they say “I guess I need to work harder” when the issue is about communication, not effort, you know you need to clarify. Second, it puts them in charge of the solution.
Now, this doesn’t mean you should accept whatever plan they propose. If they say “I’ll try to be better,” that’s not a plan.
And if their plan wouldn’t actually solve the problem, say so: “I hear that you want to focus on code quality. My concern is more about communication. I need to know when you’re blocked, not find out two days before the deadline. Let’s discuss that.”
Same if their plan isn’t quite as bar raising as you want.
A thing I see happen over and over again is managers set low expectations, maybe because they want to make it realistic, but then when the person achieves the goal they go “well, that’s still not enough”. That, to me, is cheating.
Set the right bar. If they can’t make it, so be it. But don’t give them false hopes by lowering the bar.
3. The Follow-Up Gap
Ok, the conversation is over. Phew. Good job, you!
You both agreed on a plan. It felt productive. Hard and exhausting, but good!
You check it off your mental list: “dealt with the performance issue.”
Except you’re not done.
Nothing happens for two months. You’re busy, they’re busy. Life goes on.
But when you meet again for their next review, nothing has improved.
Here’s the catch: the conversation isn’t the work. The conversation is just the trigger. Everything that happens after the conversation is what actually matters.
Some managers don’t follow up because they treat the performance conversation as a one-time event instead of the start of a process. You had the hard conversation, so now it’s on them to fix it, right?
Wrong. You need to keep correcting, giving feedback, guiding them.
Here’s what good follow-through looks like:
Before you leave the room, schedule the next check-in. Not “let’s touch base in a few weeks.” Specific date, specific time. Put it on both calendars right then.
Between check-ins, pay attention and give them feedback. Don’t let small slips accumulate into big patterns again.
At the check-ins, review concrete progress against the plan. If they did progress, acknowledge it. If they didn’t, ask why not.
Document everything. After each check-in, send a summary email. You want to make sure they have in writing what has been discussed. Remember, everyone remembers conversations differently. Writing it down eliminates ambiguity.
The Bottom Line
Performance conversations don’t get easier by avoiding them.
Have you been putting off a performance conversation because you’re nervous? Stop waiting. The conversation you’re avoiding is getting harder every day, and the performance issue is getting worse.
Have the conversation this week. Use these strategies. Pay attention to what works and what doesn’t.
Because the skill only improves when you use it.
You can do it.