The art of asking questions with columbo

The best sales question or the best answer. What’s your focus? It helps to be well-informed, but asking good questions is more important. Do you remember Columbo?

The suspect is at ease, but then Columbo strikes and says, “Just one more thing.” The confident suspect gives himself away, and you can already hear the sirens. What a setup, and what perfect timing.

I think salespeople can learn something from this famous and recurring moment. It’s hilarious because the plot never changes, so we know exactly what’s going to happen. In sales, the element of surprise also provides excellent insight.

Asking questions is generally very important, but there is a proper order to follow.

• Learn to Ask Questions First
• Knowing What to Ask
• And finally, the timing of the sales inquiry

Learning to Ask Questions

When I first started in sales, a sales coach told me, “Just ask as many questions as you can.” And he was right. Of course, the quality of your questions matters, but just start by asking questions. So I always prepared seven questions—the number of questions doesn’t matter, but it’s something you can control. So just pick a number.

I used that minimum of seven sales questions for many years until I internalized them. And it became a habit. Of course, there were many tacky questions, but I always let the customer say “stop” first. By the way, simple questions are fine at the beginning of the conversation—but avoid questions you could have already answered through your social selling approach.

Knowing What to Ask

Later, I learned what to ask and how to ask it. I became a bit more of a detective, but certainly no Colombo. This “grumpy” detective has a 100% conversion rate. I believe many salespeople think they’re prepared just by being well-informed, but that’s actually a lazy mindset.

It’s laziness, because being well-informed is about “knowing.” And selling is about understanding. It’s not your answers that matter most; it’s the questions that make you stand out. When it comes to great answers, Google beats any salesperson with ease. The search engine has a much faster processing speed and more memory. But salespeople who ask great questions will control the narrative and pave the way for better answers.

Asking the right question is an art. Good questions generate excitement because you’ve switched off autopilot and the conversation can begin.

Timing of Sales Questions

But let's also talk a little bit about timing

You know exactly what that feeling is like right after a great meeting. You walk to your car with a gentle smile, turn on the radio, and daydream for a moment, because your pitch was also fantastic. And then you suddenly ask yourself: Why didn’t I ask that question one more time, like Colombo did?

I'll tell you why...

You were focused, you prepared yourself, but you fell in love. Or at least you were “weak” for a moment there. The meeting went better than expected, and your ambition dropped to zero at the last minute. You still had a few questions, but it was already a nice meeting, so maybe next time? Maybe there won’t be a next time?

Sales questions are crucial, but it's the final seconds that can really make a difference.

It’s a matter of empathy, and that requires a different kind of preparation—something we focus on specifically during our social selling training.