How to Deliver Bad News (in B2B Sales)

Good Morning. For years, customer service reps have been asked: “Are you a real person?” Now, the tables have turned. People are sending their AI agents to sit on hold, cancel subscriptions, and negotiate bills for them. And customer service reps are starting to ask whether the customer is actually AI. Wild times we’re living in. For the record, The Follow Up is still 100% human. Now, let’s get into today’s Follow Up. (:

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In 2019, three researchers ran 11 experiments to learn more about how people react to bad news.

They found that people will like you less for bringing them bad news.

Even when you didn’t cause the problem. Or when you have nothing to do with the bad news.

Think of the airline agent who has to announce a canceled flight. They didn’t break the plane or order the thunderstorm. But guess who gets yelled at…

In sales, you get plenty of chances to be that gate agent.

The product you sold someone breaks. Or a big deal falls through. Or your company changes the compensation plan.

Today, we’re breaking down how to deliver bad news without giving someone a second reason to be upset with you.

This one is simple. Make sure you do your homework.

Know what happened, who it affects, and what questions they’re probably going to ask.

If something is still unknown, tell them.

Bringing bad news to someone already sucks enough. And it’s even worse if you have to go back and say, “Actually, I was wrong about that.”

In Moneyball, Oakland A’s general manager Billy Beane has his assistant, Peter Brand, role-play cutting a player from the team.

Peter starts by saying how much the player means to the team, and how it’s a tough decision, blah, blah, blah...

Billy Beane says: “Be straight with them. No fluff. Just facts.” and then shows him how to do it: “Pete, I gotta let you go. Jack’s office will handle the details.”

Here’s the clip from the movie.

I know that’s just a movie scene, and movies aren’t real life. But that advice is solid.

Here’s how you can use it in a sales environment:

❌ “We’ve run into a few challenges around the timeline we originally discussed.”
✅ “We won’t meet Friday’s launch date due to an engineering delay. We need to move the launch to next Wednesday.”

With your boss, it might sound like:

“The deal won’t close this quarter. The buyer confirmed that today, so I’m taking it out of my forecast.”

Put that before the long story about who emailed whom, and why it’s not really your fault.

Getting to the point quickly also leaves more time for questions because most people who get bad news will have more questions than Carlos in Moneyball.

Back in 2021, a video showing the CEO of Better.com laying off 900 people over Zoom leaked online.

Before telling the employees on the call they were losing their jobs, he talked about how hard all of this was for him. In the recording, he said: “The last time I did it I cried, this time I hope to be stronger.”

Dude. 900 people are about to lose their paychecks. Nobody wants to hear about how hard this is for you.

That’s like backing into someone’s car, then asking them to cheer you up because you’ve had a rough morning.

Don’t make it about yourself → Take responsibility for what happened.

If you made a promise you couldn’t keep, own it: “I gave you that date before I checked with our delivery team. That was my mistake. I’m sorry.”

Then let them talk.

Give them room to be upset. They don’t owe you a cheerful response.

When someone is upset, it’s tempting to make a big promise to help them feel better.

Something like, “We’ll have it fixed by Tuesday” might calm them down in the short term. But if you’re not positive that you can deliver that promise, you’re setting yourself up for more bad news. (Not to mention, you’re rapidly burning their trust).

Tell them what you can actually commit to. If you don’t know when the fix will be ready, say so and give them a time for the next update.

“I’m checking with our delivery team tomorrow morning. I’ll call you by noon with what we know.”

Then do what you promised.

Today’s newsletter was written by Nic Conley