Ever asked a prospect a “Why” question, only to sense a shift—maybe even defensiveness?

It happens more than you think. And it might be costing you opportunities without you even realizing it.

When prospects share insights, it’s natural to want to understand their reasoning. But if you ask, “Why do you do it that way?”, you might inadvertently trigger a defensive reaction.

Why questions often feel like a challenge.

Think about when you were a kid and an adult asked, “Why did you do that?” chances are, you felt like you had to justify yourself rather than explain your reasoning.

Instead of “Why do you do it that way?”, try “How did you and your team develop that approach?”

“How” invites conversation. It shows curiosity without making someone feel like they need to justify their choices.

Context matters. A why question to a newly hired leader might prompt them to rethink inherited processes. But the same question to a long-tenured individual could feel like questioning their expertise.

Both why and how get to the reasoning behind decisions but how keeps the conversation open, collaborative, and productive.

So next time you’re in a sales conversation, pay attention to the questions you’re asking. A simple shift in wording can make all the difference in building trust and keeping the discussion moving forward.

Share this...