How to Have Hard Conversations

or "don't wait, seriously, say the real stuff."

Most people avoid hard conversations. Or they wait too long. And by the time it finally happens, it’s messy. Too emotional, too vague, too late.

It doesn’t have to be like that.

You can say the hard thing early and clearly, and still walk out with trust intact. You just need a plan. Here’s a four-part approach I share with clients who need to have the RealTalk™ conversation but don’t know how. I didn’t invent it, and I may be misremembering where I saw it, but I know this: it works.

1. Say up front: this is going to be a hard conversation

No drama. Just name it.

“Hey, I want to have a hard conversation with you.”

That line does a lot. It shows respect. It gives the other person a second to brace. And it sets the tone: this is a direct conversation, not a surprise attack.

2. Preview what we’re going to talk about

“There are three things I want to cover: A, B, and C.”

You’re laying down a map. It gives focus and structure, which helps when emotions run high. Even if the topics are hard, they’re not hidden. You’re showing up prepared, and that helps the other person do the same.

For example, “I’m frustrated that we haven’t hit our goals and you haven’t made meaningful progress in the past few quarters.” And, “I hate that I have to be the one to hold everyone accountable when I see that as your role.” And, “this needs to change or we can’t continue this way.”

3. Say how you want to walk away

“My goal is that we leave this aligned and moving forward.”

Or: “We may not agree on everything, but we’ll know what’s next.” Or: “Even if it’s tough, I want to come out of this with clarity and respect.”

This resets the temperature. You’re not picking a fight. You’re being honest about where you’re trying to land. That helps people stay engaged instead of getting defensive.

4. Ask for agreement

“Is that okay with you?”

This might be the most important part. When someone says yes, even quietly, the whole dynamic shifts. You’re not doing something to them. You’re having the conversation with them.

More often than not, they have been waiting for you to have this conversation. They’re smart and they know you’re not aligned.

This structure doesn’t make the conversation easy. But it makes it better. Cleaner. More productive. It’s helped leaders fire people the right way, give feedback that actually lands, and work through tension without losing the relationship.

It lines up with what the authors of Difficult Conversations talk about: clarity up front builds safety. And it mirrors ideas from Crucial Conversations, that the way you open a conversation shapes everything that follows.

Give this a try and let me know if works.

I write for CEOs and leaders who want to get better at the hard parts. If this helped, share it with someone who’s got a hard conversation coming up. Or #leadership #howtoceo #coaching #startups #management and tell me how you’ve handled these moments.