What Columbo Can Teach You About Selling Smarter

Columbo and Selling: Why "Not OK" Beats Being a Know-It-All

A great salesperson isn’t the one who always has the perfect pitch, the slick response, or the answer to everything. It’s the one who knows how to create a real connection. And to do that, they first have to lower the prospect’s defenses.

Why are those defenses there in the first place?

Because prospects are afraid—afraid of being manipulated, of giving away information that could be used against them. Not because they’re paranoid or unfriendly. It’s just human nature. And let’s be honest, you don’t exactly trust every salesperson you talk to either, do you?

These defenses make it impossible to build a relationship of equals. So it’s on the salesperson to adapt—to shift how they show up. And that often means letting go of the need to look sharp and in control. That’s where the concept of being “Not OK” comes in—borrowed from transactional analysis.

Be a bit less OK than your prospects

This psychological framework explains how we interact with others through different ego states (Parent, Adult, Child), and how we seek out interactions that make us feel OK about ourselves. In fact, we often prefer situations where we feel a little more OK than the person we’re talking to.

That’s exactly what Columbo does. He’s not trying to sell anything—he’s trying to get a confession. And his genius? He never shows up as the tough cop. He plays the confused, rumpled, slow-talking guy who “just has one more question.” And his suspects? They let their guard down. They feel smarter, more in control. And they talk.

Watch this clip: You’ll see how deliberately he plays being “less ok” than the suspect’s in order to gain trust and get information.

So ask yourself: when you’re selling, are you the superhero who always knows best? Or are you more like Columbo—curious, humble, comfortable not having all the answers, and focused on making your prospect feel OK?

In a world where buyers are on guard, dropping the mask of perfection might just be your strongest sales move.
Less cape and tie. More crumpled raincoat.