Why Some Leaders Avoid Hard Conversations (And What the Best Ones Do Differently)

I coach leaders for a living. And one of the patterns I see more than almost any other is this: a smart, capable, well-intentioned leader who knows exactly what conversation they need to have... and just can't bring themselves to have it.

Let me tell you about two of them.

I was working with a leader named David. Good guy. Sharp. Cared deeply about his team. During one of our coaching sessions, he told me with real conviction, "This is the week. I'm going to talk to him."

I believed him. He believed himself.

When I checked back in the following week, David said it just wasn't the right time. The week after that, he'd had some bad health news and didn't have the energy. The week after that, he was "just not feeling great."

Here's what eventually came out: this situation hadn't been brewing for a few weeks. Not even a few months. It had been years.

Years of knowing something needed to be corrected, years of finding reasons not to correct it. And then, as these things always do, the situation forced itself. David didn't get to choose the time, the place, or the terms. What landed in his lap was something far uglier than the original conversation ever would have been. It involved legal counsel. It could have been avoided a long time ago.

David wasn't lazy. He wasn't weak. He was doing what most people do when they think about a hard conversation. He was putting the process first. The discomfort. The awkward silence. The other person's reaction. The knot in his stomach. That's all he could see. And when that's all you can see, avoidance feels like the smart play.

Until it isn't.

Now let me tell you about Sarah. Sarah had a conversation ahead of her that she genuinely did not want to have. The kind where you know the other person is going to be hurt, there are going to be consequences, and some of those consequences are going to be expensive.

Nobody would blame her for putting it off.

But Sarah did something different. She started picturing what it would feel like after. Not during. After.

She kept coming back to one word: clarity. She knew that once the conversation happened, there would be clarity. And from clarity, a plan could be built. A path forward. She didn't pretend the negative consequences wouldn't exist. She just refused to let them be the only thing in the frame.

So she had the conversation. And predictably, the other person had an emotional reaction. It wasn't fun. But Sarah stayed with it. She didn't retreat, didn't apologize for the truth, didn't rush to make it comfortable.

And then something interesting happened. The worst possible outcome never showed up. In fact, both Sarah and the other person walked away feeling something close to peace. And everything between them from that point forward got easier.

Here's what I've come to believe after years of coaching leaders through moments like these:

The leaders who avoid hard conversations and the leaders who have them are not different breeds of people. They're not wired differently. They don't have some courage gene the rest of us are missing.

The difference is where they point their attention.

The ones who avoid put the process front and centre. The short-term pain. The anticipated discomfort. The look on the other person's face. They rehearse the worst moment of the conversation over and over until it becomes the whole story. And naturally, they don't move. Or if they do, they're in such a terrible frame of mind that it doesn't go well anyway.

The ones who act put the outcome front and centre. They picture resolution. Clarity. A better relationship on the other side. The relief of not carrying it anymore. They still feel the fear. They just refuse to let it be the loudest voice in the room.

That's it. That's the difference. It's not about being tough. It's about where you choose to look.

If you're a leader right now and there's a conversation you've been putting off, I want you to try something.

Don't think about the conversation itself. Think about what it would feel like to have it behind you.

Picture the clarity. Picture the plan. Picture the relationship — maybe not perfect, but honest.

Now ask yourself: is the discomfort of having it really worse than the weight of carrying it?

I already know your answer.

Next week in Hard Conversations: ever notice how your whole body tenses up the moment someone says "Can I give you some feedback?" There's a reason for that. Your brain is wired to treat feedback like a physical threat — and until you understand why, every hard conversation starts with you already on the defensive. We're going to change that.

— Troy