How to Sell to Someone Who's Already Had a Bad Experience

Good Morning. Yesterday, OpenAI released GPT-Live, which is their new voice model that’s supposed to make talking to AI feel a lot more like talking to a real person. Apparently, it can listen, respond naturally, avoid awkward interruptions, and even say things like “mhmm” so you know it’s paying attention. Which is impressive, but I’ll only believe AI can replace salespeople when it can get weirdly nervous the second a prospect picks up the phone, forget its opener, and somehow still book the meeting. That’s what real selling is all about. Now, let's get into today's Follow Up. (:

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A while back I was shopping for a used car.

I'd already been to a few dealerships and had a trade in offer I wasn't happy with. When I told the next salesperson the number, he shrugged and said "Yeah, that sounds about right. Probably about the same as what we'd do."

Cool. Thanks for nothing.

The salesperson at the next dealership heard the same number and said "Oh man. I bet you were hoping for more than that. I know I would be. Let me see what I can do - I want to make sure you walk out of here with the highest trade in value possible."

He came back with almost the exact same number. Didn't matter. I bought from him anyway.

He made me feel like he was actually on my side. Like my frustration was a problem worth solving and not just a fact of life to shrug at.

That's the clear difference between a rep who loses when their buyers already had a bad experience, and a rep who finds a way to win the deal.

A prospect who's been burned before is actually a better buyer the second time around.

They've already survived a full buying process. So they know exactly what questions to ask, what went wrong, and precisely what they never want to experience again.

It’s easy to look at these skeptical buyers as an uphill battle, but in reality, they give you an easy angle to sell against.

They've already done their research. So they'll tell you their pain points, their dealbreakers, and their priorities without you having to dig for them.

Now let’s talk about how to actually sell to them.

The first thing a burned buyer needs is for someone to actually acknowledge what happened.

They don't want your pitch, and they don't want you to gloss over their bad experience with a quick "yeah, that happens sometimes" before pivoting to your product demo.

They want to feel heard. (don’t we all…)

Think about what a good therapist does. They listen and validate, and make you feel like your experience genuinely matters before they offer any advice.

The best response when a prospect tells you about a bad experience sounds something like this:

"I see this all the time, and I'm sorry you went through that. I really hate to hear it. Can you walk me through exactly where things went wrong last time?"

That one sentence validates their frustration and then opens the door for them to tell you exactly what went wrong… (which is the most valuable information you can get before your pitch).

Once they've told you what happened, isolate the exact issue.

Was it implementation? Support? Did pricing change after they signed? Did the product not do what they were promised?

Getting specific matters because "I had a bad experience" is too vague to sell against. But "their onboarding took four months and we never got a dedicated rep" is something you can directly address, and guarantee that it won’t happen again.

Now you can say something like "Here's exactly how our onboarding works. You'll have a dedicated rep by day one. The whole process takes 30 days. And here's my direct number so if anything goes sideways, you're not submitting a ticket into the void."

Instead of trashing the last vendor, focus on solving the exact problem they already handed you.

And because you listened first and validated what they went through before pitching anything, they actually believe you mean it.

Check out The Follow Up Guy on LinkedIn.