How to Let Someone Down Without Destroying the Relationship

Letting someone down is one of the hardest conversations we face. Whether it’s in business, leadership, healthcare, or family life—most people dread it. We hesitate, avoid, delay… and when we finally do it, it feels like we ripped a Band-Aid off someone else’s face.

But it doesn’t have to be that way.

I’ve had to let people down in negotiations as a cop, as a coach, as a friend, and in business. And the thing I’ve learned is this: people don’t usually remember the “no.” They remember how you said it.

Let’s break this down.

Why We Struggle to Say No

It really depends on your type. Accommodators? They’re terrified of hurting the relationship. Assertives? We think we’re helping by being quick and clear, but we might come off cold or abrupt without realizing it.

Most of the time, it’s not the content of the bad news that creates the discomfort—it’s the emotional weight of delivering it. We’re worried about how we’ll be perceived. We don’t want to be the bad guy. Or we don’t want to feel that twist in our gut when we disappoint someone else.

So we stall. We say nothing. And that silence? That avoidance? That’s what actually erodes trust.

People can handle bad news. What they can’t handle is uncertainty and avoidance.

It really depends on your type. Accommodators? They’re terrified of hurting the relationship. Assertives? We think we’re helping by being quick and clear, but we might come off cold or abrupt without realizing it.

Most of the time, it’s not the content of the bad news that creates the discomfort—it’s the emotional weight of delivering it. We’re worried about how we’ll be perceived. We don’t want to be the bad guy. Or we don’t want to feel that twist in our gut when we disappoint someone else.

So we stall. We say nothing. And that silence? That avoidance? That’s what actually erodes trust.

People can handle bad news. What they can’t handle is uncertainty and avoidance.

The Real Purpose of Tactical Empathy®

When we teach Tactical Empathy®, it’s not a strategy for “being nice.” It’s about making people feel heard—especially when things get uncomfortable. And it starts well before the bad news ever shows up.

If you’ve built trust from the beginning—if you’ve demonstrated curiosity, connection, and humanity—their ability to receive a hard message from you skyrockets.

Because they’re not just hearing the news. They’re hearing it from you. Someone they trust. That changes everything.

Bad news doesn’t have to be the end of a relationship. Done right, it can deepen the relationship.

Structure Matters: How to Use Accusations Audits™ Before Letting Someone Down

When you're about to let someone down, you need to lay the groundwork with Accusations Audits™—before the actual conversation even begins.

Start with something simple, like:

“You probably have a thousand other things you’d rather be doing right now than talking to me about this…”

This is where you front-load empathy ,early and generously. Call out the negatives. You’re not confessing—you're defusing.

Example:

“You’re probably really annoyed with how long it’s taken me to come to a decision…”
“You might even feel like I’ve dragged my feet on this…”
“You may be wondering if I even care about how this affects you…”

Speak those thoughts out loud before they take root in their heads. Clear their heads of the negatives so that they hear you when you finally get to the point.

Letting Them Down: The Phases “No”

You don’t have to drop a hard no like a guillotine.

Instead, use what we call Phases of No; each prefaced a small dose of Tactical Empathy®

1. Prompt them to think with Calibrated Questions™️

“I’m sorry…how are we supposed to make this work with everything else going on?”

Let them do the math. Let them help solve it—even if the answer is ultimately no.

2, Ease into the refusal

“I’m afraid that I just don’t know how we’re going to make that work this year…”

You haven’t said “no” directly, but you’ve planted the reality.

3. Convey that you are ready to walk without cornering them or yourself

“This is going to feel like a huge setback. We just can’t do it.”

The goal is not to avoid discomfort. The goal is to let the other person feel seen and respected in the process. That’s what preserves the relationship.

Don’t Rush It—Use Dynamic Silence™

This is where a lot of people get it wrong. We fire off three Accusations Audits™, speed to the “no,” and move on.

Slow down.

Pause after your Accusations Audits™. Read the room. Listen with your eyes.

If someone crosses their arms, shifts in their seat, stares at the floor—you missed something. Label it.

“It seems like I may have really hurt you on this…”
“It looks like I’ve touched something deeper here…”

Let them tell you what’s really going on. The truth is in the silence, not the script.

Practice in Low-Stakes Situations

The first time you use an Accusation Audit™ shouldn’t be in a high-stakes conversation. You need reps.

And guess what? You’re negotiating all the time. That coffee shop order? That’s a negotiation.

So try this next time you’re making a request:

“You’re probably going to think I’m a pain, would you be against subbing oat milk instead?”

It might sound silly, but what you just did was infuse humanity into a transaction. You’ve connected. You’ve made space for rapport.

Do that enough times and Accusation Audits™ won’t feel weird. They’ll feel natural. Automatic. Just part of how you show up.

Final Thought: Hesitation Is a Clue

If you’re hesitating to have a conversation—ask yourself why.

That hesitation is your body telling you this is the moment to apply Tactical Empathy®.

Lean into it. Don’t push it off. Don’t default to quick, clipped communication just to get it over with. Take a breath and ask:

“How can I do this in a way that’s not just clear—but kind?”

Because that’s what great negotiators do. Not just close deals. Not just get results. But move through hard conversations in a way that builds trust instead of burning bridges.