The Conversation You’re Avoiding Is Already Happening
Good morning. Speaking of uncomfortable (see what I did there?), this week’s topic is the one my clients avoid talking about more than any other.
Think about it: is there a conversation you’ve been putting off? You know the one. You’ve rehearsed it. You know what needs to be said. You just haven’t said it yet.
A client had been meaning to talk to her VP of Operations for four months. Four months. She knew exactly what needed to be said. She’d rehearsed it in her head before every one-on-one. Then she’d spend the meeting talking about project timelines instead.
When I asked her what she was waiting for, she said she wanted to find the right moment. I asked her how many right moments had passed in four months. She stopped counting at twelve.
Here’s what I’ve noticed about the conversations leaders avoid. It’s almost never about not knowing what to say. It’s about knowing exactly what needs to be said and being afraid of what happens after you say it. Will they get defensive? Will it damage the relationship? Will it make things worse?
Meanwhile, the team watches. They see the underperformance. They see the behavior. And they see that you see it too. Every day you don’t have the conversation, you’re sending a message to everyone else about what you’re willing to tolerate. And that message is shaping your culture right now, whether you intended it to or not.
I’ll be honest, what surprised me most about this pattern wasn’t how many leaders avoid these conversations. It’s that they genuinely believe the delay is protective. They think if they wait long enough, the problem’ll solve itself, or the person’ll wake up and change, or some magical moment’ll arrive where it feels safer. It never does. The wait just gets longer and the resentment gets deeper.
There’s something else I see happen. Once someone finally has the conversation, they tell me the same thing: it wasn’t as bad as they imagined. Not always easy, but survivable. The person either heard them and shifted, or they didn’t. The relationship either held or it didn’t. But the leader’s still standing, the team saw it happen, and the culture moved. That’s the beat most people miss while they’re rehearsing.
Here’s what I don’t know: whether you’re avoiding this because you’ve had a conversation go badly before, or because you’ve never had one at all. I don’t know if your concern is about the person’s reaction or your own ability to handle it. But I know what happens next if you don’t have it. Your team watches you see something and do nothing, and they start checking out. That’s not on them. That’s on the invisible pattern you’ve created by staying quiet.
If something in this week’s newsletter described a pattern you’ve suspected but couldn’t name, that’s exactly what Executive Triage is built for. One conversation. One pattern named with enough precision that you can’t unknow it. 90 minutes, an eight-page brief, $3,500. cynthiacorsetti.com/executive-triage
Kim Scott gets at something most leadership books miss: the conversations that matter aren’t the polished ones, they’re the ones where you’re willing to say something that scares you. This book’s specifically useful if you’re the kind of leader who avoids hard conversations because you’re trying to be kind. Scott shows you that staying silent isn’t kindness, it’s the opposite.
The conversation you’re avoiding is already happening. Your team is having it without you. The only question is whether you’ll be part of it.