Here’s how to have a difficult conversation with anyone.

Most people approach hard conversations with what’s often called the “compliment sandwich.” You start with something nice, slip in the difficult part, and then try to end on something nice again. It sounds like this:

“Hey, so good to see you! How are things? How’s your family? How’s pickleball? Crazy weather, right? So listen…”

And there it is. The phrase “so listen.” Everyone in the room knows the hammer’s about to drop. The tension builds, and once that line hits, it’s downhill from there. You’ve set yourself up for failure before the real conversation even begins.

Instead, start with the truth. Begin with the difficult part. It can sound as simple as this:

“This is going to be a hard conversation.”
“This might come as a shock.”
“You’re not going to like what I have to say.”

That’s it. Direct. Honest. Human.

When my team or I have to deliver bad news, we lead with: “You’re not going to like this.” And it works—because the moment you say it, the other person braces for the absolute worst. Then, when they hear the real news, it almost always lands softer than what their imagination created.

Think about it: ever gotten a text that just says “We need to talk”? Your brain immediately goes to the worst-case scenario. “Did someone die?” “Am I getting fired?” “Are we breaking up?” Or maybe you’ve gotten that one-word reply—‘K’—from your partner and thought, “Well, I guess that’s it. We’re done.”

That’s your biology kicking in. The fear of the unknown triggers your anxiety and sends you scanning for danger. By dragging out small talk before bad news, you only amplify that fear.

So instead of circling around it, get to the point. Skip the pleasantries and say right away:

“This is going to be a difficult conversation.”
“I’m not looking forward to this.”
“You’re not going to like what I have to say.”

Say it clearly, then pause. You’ll notice the person take a breath, reset, and prepare themselves. That pause gives them time to regulate before you deliver the message.

What you’re actually showing is respect—you believe in their emotional stability. You’re saying, “I trust you can handle this.” That’s far kinder than trying to protect them with small talk or false warmth. The small talk usually isn’t about them anyway; it’s about us. We’re afraid of disappointing someone. We’re afraid they’ll stop liking us. That’s the people-pleasing instinct talking.

But the truth is, being direct is being kind. Clarity is kindness. So next time you have to deliver bad news, drop the filler, start with honesty, and then speak your truth calmly and clearly.

Because real respect starts with straightforward communication.