Kicking the Can: The Cost of Avoiding Hard Conversations

We’ve all been there. You know the conversation needs to happen. You’ve been frustrated for weeks (or months). Expectations aren’t being met. Performance is slipping. Your patience is wearing thin. But instead of addressing it, you kick the can down the road.

You justify it to yourself: “They should know better.” “Maybe it’ll get better on its own.” “I’ll deal with it later when the timing is better.”

Spoiler alert: it never gets better on its own, and the timing is never perfect.

The truth is, by avoiding these conversations, you’re doing more damage than you think. Not just to your team or your company, but to yourself.

I once heard a great line from a client’s 360 review:

This hit me hard because it’s true. When you hold back, people know. They feel it. Your body language gives you away. Your tone changes. You’re not as present or engaged. It is obvious.

Even if you think you’re sparing someone’s feelings or maintaining harmony, you’re creating an undercurrent of tension and mistrust. Your team starts to sense that something’s off. They might not know what, but they feel it. And it impacts them.

Why do so many CEOs and leaders avoid these hard conversations? It’s usually because they don’t want to be the bad guy. They don’t want to deal with the discomfort. They’re worried about damaging relationships or hurting someone’s feelings.

Or they think they’re making a trade-off for other short-term priorities. “I just need them to close the quarter and THEN I’ll give them this rough feedback.”

But here’s the kicker: by avoiding it, you’re doing all of those things anyway—just slowly and quietly.

I’ve seen this play out time and again, which is why I always come back to RealTalk™. It’s about being direct, candid, and honest. It’s about getting to the point without dancing around the issue. And yes, it can be uncomfortable. But it’s also liberating.

Having the hard conversation not only clears the air but builds trust. It shows your team that you respect them enough to be honest. It sets clear expectations and paves the way for growth.

As Mike Vrabel of the New England Patriots said, “great players want to be told the truth.” This resonates because it’s about respect. If you truly care about someone’s growth and success, you owe them honesty—even when it’s uncomfortable. Especially then.

I get it. It’s hard. But the longer you wait, the worse it gets. The stakes get higher, the issues get bigger, and the tension grows thicker.

So rip off the band-aid. Have the conversation. Say what needs to be said. And then listen. Really listen.

Because there’s a lot of content in the unsaid—but there doesn’t have to be.

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