You're allowed to ask 'why'

I was on a coaching call recently with a group of people selling IT services.

We were working through discovery questions, and there was a perfect moment for someone to dig deeper into something the prospect had just said.

One of the guys on the call jumped in: “What we could have asked here is, ‘Why is that important to you?’”

Another person immediately responded: “Wait—I thought we weren’t supposed to ask ‘why’ questions. That’s what Chris Voss says.”

And look, Chris Voss is a phenomenal hostage negotiator. His book Never Split the Difference is excellent. A lot of his content gets used in sales because negotiation and sales overlap—especially around the psychology of getting what you want.

But there’s one piece of his advice that’s being implemented way too broadly.

Chris says don’t ask “why” questions because they tend to make people defensive.

When you say, “Why did you do that?”, it triggers something in people. From a young age, we’re trained to interpret that question as an accusation. Like we’ve got to defend our position or justify our action.

And if you’re trying to negotiate with someone—especially in a hostage situation—making them defensive is the last thing you want.

I fundamentally agree with this. It’s solid psychology.

But here’s where I think people are implementing it too broadly.

Keep in mind that Chris comes from negotiating with terrorists and hostages.

There’s inherent conflict in that situation. You’re on opposite ends of the spectrum with conflict sitting right between you.

That’s not sales. Or, at least it shouldn’t be.

If you’re running a consultative sales process, their money isn’t being held hostage. You’re not in an adversarial relationship.

The entire premise is different.

Here’s what I think people miss when they take this advice too literally.

Let’s say someone tells you they’re doing something a specific way. You could ask:

Question 1: “Interesting… I haven’t seen that approach before. Why do you guys do it that way?”

That’s going to land perfectly. Why? Because you’re genuinely curious. Your tonality says I’m curious.

The person can hear that you want to understand their thinking.

Now compare that to:

Question 2: “Well… what’s the purpose of that?”

That’s going to put them on their heels. Even though it doesn’t start with “why.”

Here’s the irony: According to the “rule,” you’d avoid Question 1 (it starts with “why”) and use Question 2 (it starts with “what”).

But in actual practice, Question 1 works perfectly and Question 2 makes people defensive.

Because it’s not about the word that the question starts with. It’s about the intention and tonality behind it.

So here’s the bottom line: You can use “why” at the beginning of a question.

Use it when you’re genuinely curious. Deliver it with the right tonality. Approach it from a position of curiosity, not accusation.

You’re gonna be fine. Don’t overthink it.

Use “why” strategically. But keep asking really thoughtful questions.

Adios,

Ray

P.S. — The best sales advice gets ruined when people turn it into rigid rules instead of understanding the principle underneath. Chris Voss’s work is about reading people and adapting. Ironically, rigidly avoiding “why” questions is the opposite of that.