The Art of Inquiry: Asking Great Questions

Over the years, I have observed a skill that is often lacking in today’s entrepreneurs. I call it the art of inquiry, but in its simplest form what I mean is asking great questions. When entrepreneurs encounter failure, whether it be not meeting a particular business goal, a product launch that crashes and burns, or a business process that gets derailed, I’ve found it can often be traced to a failure to ask questions. Even more frustrating is when you realize that the question did occur to you but you put aside to get on with the work. In today’s rapidly-changing business landscape, asking great questions isn’t a luxury – it’s a necessity.

Why Asking Great Questions is Hard

Part of what’s going on here is a failure in the way we educate. When kids are around the five, they’ve developed just enough that they start asking lots of questions. This is a good thing, even if some parents find it a bit frustrating at times. But then they go to school, and the plain fact of the matter is that most schools train students on finding and giving answers rather than asking great questions.

Think about what else goes on in school. It’s the teachers who ask the questions, right? And no student wants to look “dumb” by not knowing the answers, so they stay silent and don’t ask questions. It’s a lose-lose situation.

Layer on top of this our need for speed. Who’s got time to even ask questions, let alone pursue answering them? But if you don’t slow down and ask questions, how do you know what you’re doing is going to get the best results possible? Asking great questions is the absolute core of being innovative.

Modern American culture simply doesn’t value effective inquiry. Entrepreneurs especially feel the need to project an image of being certain of the answers. Asking great questions feels like some kind of weakness.

Regaining the Skill of Asking Great Questions

Asking great questions is a skill every entrepreneur needs to develop. It begins by training yourself to not dismiss those questions that pop into your head. Not every question is a great question, though, so you need to know what makes for great questions. All great questions should be empowering, meaning they lead to thoughtful discussion and further inquiry. They serve to do one or more of the following:

  • Challenge assumptions.
  • Enable a different view of a situation.
  • Get people reflecting on their behaviors.
  • Elicit discussion by being open-ended.
  • Lead to confidence and courage.
  • Result in effective action.

Anthropologist Claude Levi-Strauss once said something worth remembering about inquiry: The wise man doesn’t give the right answers, he poses the right questions. Your success as an entrepreneur depends on all kinds of factors, one of which is your skill in asking great questions. 

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