The Conversation You're Avoiding Isn't Getting Easier

Sep 22

You're optimistic, even hopeful. But you’re also nervous and a little concerned. There's a problem that you've been having with an employee, and you're hoping it goes away on its own because you don't want to have that conversation.

But you know what? It's not going to get any easier the longer you wait. In fact, it's probably going to get harder the longer you wait, and the problem may get bigger.

What's actually holding you back?

There's usually a very specific reason, and it's rarely “I have no time."

The former peer, now your direct report. You're worried this conversation costs you the friendship.

The employee who's sharper than you in the room. What if they push back and you don't have a good answer?

The one who happens to be close with your boss. Could this get complicated for you?

The person everyone knows has a short fuse. You're bracing for an argument before you've even opened your mouth.

The genuinely good employee having an off few weeks. You don't want to make this a bigger deal than it is.

Sound familiar? Pick the one that's yours.

Here's the thing. You're not actually waiting for the right time. You're waiting to feel less uncomfortable. That feeling isn't coming. Ever. So we might as well stop waiting for it.

Waiting has a cost, and you're the one paying it

While you wait, the behavior keeps happening. Your frustration keeps building. Other people on the team start noticing that nothing's being said or done, which tells them something too. And the employee? They don't get the chance to fix something they might not even realize is a problem.

Here's the part that gets managers into real trouble. You start keeping score. Six weeks of small annoyances turn into one very large mental file, and by the time you finally sit down to talk, you're not addressing a behavior anymore. You're unloading a case.

Early conversations are course corrections. Delayed ones turn into confrontations. Big difference.

Get clear before you open your mouth

Before the conversation, get honest with yourself about two things.

First, name your own hesitation. Is it the relationship? The possibility of conflict? Politics? Simply not being sure of your footing? You can't manage the conversation well if you haven't managed your own reaction to it first.

Second, separate what actually happened from what you've decided it means.

"You're not committed to the team" is a conclusion. It's also something they can, and will, argue with.

"You've missed the last three deadlines, and I didn't hear from you ahead of time that they were at risk" is a fact. It's specific, it's true, and there's nothing to defend against because it's just what happened.

Start there.

Read the person, not just the problem

The issue you need to raise doesn't change. How you raise it should.

Some people want you to get to the point immediately. Others need a little context first, or time to sit with something before responding. Some want the receipts, the specifics, the timeline. None of that is you softening the message. It's you making sure it actually lands instead of bouncing off.

That's what people-first leadership looks like in practice. Not a slogan. Just paying attention.

Plan the conversation. Don't script it.

Know your opening line. Know the specific behavior. Know the impact. Know what needs to change. Know the one question you want to ask.

Then follow this:

Here's what I've noticed. Here's why it matters. Here's what I need going forward. What's your perspective?

Then stop talking. Actually listen to the answer, because you might be missing part of the story. You usually are.

Your Turn

Reflect: What conversation have you been putting off, and which reason from the list above is really yours?

Assess: What are the facts, not the story you've built around them?

Engage: Put the conversation on the calendar this week. Not "sometime." An actual date and time.

You're probably never going to feel fully ready for this conversation. That's not really the goal. The goal is knowing you can handle the discomfort well when it shows up. You can't always make the conversation comfortable. You can make sure you're prepared for it.