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Chris Voss is Wrong About 'Why' Questions (And Here's Why)
I was on a coaching call with people selling IT services, and someone had an opportunity to dig deeper into what the prospect said. Another person suggested, "We could have asked 'Why is that important to you?'" The response? "I thought we weren't supposed to ask 'why' questions. It's what I heard from Chris Voss." Look, I love Chris Voss—phenomenal hostage negotiator, great book (Never Split the Difference)—and I fundamentally agree with most of what he says. He's right that "why" questions can make people defensive because we're trained from childhood that "Why did you do that?" means we're being accused of something. But here's my slightly different perspective: Chris comes from negotiating with terrorists and hostages—there's inherent conflict between the two parties. That's not consultative sales. Your prospect's money isn't being held hostage. This episode breaks down why the advice gets implemented too broadly without understanding the context. If you ask with curiosity—"Interesting, I haven't seen that before... why do you guys do it that way?"—versus accusation—"Well... what's the purpose of that?"—your tonality changes everything. I hereby give you permission to use "why" at the beginning of questions, so long as you deliver it with curiosity and not accusation. Don't overthink it. Use it strategically.
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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.
About Ray:
→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.
→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.
→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com
→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.
→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com
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Transcript
I'm not supposed to ask questions that start with "why." That's what I heard recently on a coaching call. I was talking to a bunch of people who are selling IT services. We were talking about discovery questions and there was an opportunity for somebody to kind of dig in to something that the prospect had said. And, you know, somebody on the call said, "Well, you know, like what we could have asked here is, 'Why is that important to you?'" And, you know, the person responded and said, "Well, I thought we weren't supposed to ask 'why' questions. It's what I heard from Chris Voss."
And it's... Chris Voss is a very accomplished, you know, hostage negotiator, has a, you know, phenomenal book, Never Split the Difference, and a lot of his um... a lot of his content is used in sales because it's negotiation-based, right? And a lot of what he talks about is the psychology of, you know, effectively negotiating and, you know, at the end of the day getting what you want.
This is something that he says. He says, you know, don't don't ask "why" questions because it tends to make people defensive. When you say like, "Why did you do that?", you know, from a young age you kind of like trained to go: "Shit, I'm being accused of doing something, so now I've got to defend my position or justify my action." And so it has the potential to make people defensive, which isn't isn't what you want when you're trying to get what you want, right? Out of a negotiation.
And I... first of all, I love Chris Voss. Uh, you know, recommend a lot of his content and uh fundamentally I agree with with most of the things that he says. But I've got a slightly different perspective on this one when it comes to questions that start with "why." And I think it's implemented too broadly without understanding why uh he's saying it, right?
So first of all, like keep in mind Chris comes from negotiating with with terrorists and hostages, okay? So there's inherent conflict in that in that situation, right? Between the the two people. Like there's... you are at opposite ends of the spectrum and there's conflict like sitting right in between you. And I don't think that that's sales. Like if you're if you're running a consultative sales process, you're not... it's not a hostage situation, right? Like you... their money is not being held hostage that you need to get back, okay? So first of all, like there's just a completely different premise with with the two things.
But I also think that if you ask the question with curiosity, like "Hey, why does that matter to you?" Because if if I ask somebody, if they, you know, they tell me that they're doing something a specific way and I go, "Interesting... I haven't seen that before. Like why... why do you guys do it that way?" That's gonna land fine, right? Like that's... I'm curious. And my tonality says I'm curious. That's not the same thing as, "Well... what's the purpose of that?" Right? Like that's... again... just like using some some different examples.
So, um, you know, when I when I think about this, like, I hereby give you permission to use "why" at the beginning of a question so long as you're being curious, so long as you deliver it with the tonality that's going to, you know, elicit or get the response that you want. And, you know, as long as you approach it from a position of curiosity and not accusation, you're gonna be fine.
So, don't overthink it. You can use "why." Use it strategically. But still continue to ask really thoughtful questions. Hope it helps. Adios.
