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The Art of Asking Dumb Questions

The Art of Asking Dumb Questions

As coaches, our business is simple: catalyze results. If our clients aren’t achieving better, bigger, and more profitable outcomes than they would on their own, we’re falling short.

Fortunately, we have an arsenal of tools at our disposal. For example, we can:

  • Offer perspective
  • Provide context
  • Help connect dots
  • Articulate their vision
  • Lend structure
  • Guide them to a process
  • Create peer accountability
  • Model leadership
  • Point out distinctions
  • Relate experiences
  • Shine a light on mistakes
  • Suggest solutions
  • Develop strategies
  • And so much more.

These tools are invaluable, but there’s one that stands out: asking questions. Why? Because people love their own ideas. Questions engage their minds, trigger answers, and spark the kind of “aha” moments that lead to real action.

Here’s the kicker: the most productive questions are often the “dumb” ones. These are the questions most people are too shy—or too intimidated—to ask, even when things don’t make sense.

Why Dumb Questions Matter

“Dumb” questions challenge assumptions, clarify confusion, and uncover gaps in understanding. They’re especially important in areas where expertise can feel intimidating.

Take accounting and finance, for example. After 20 years as a CPA, banker, and investment banker, I’ve seen how often clients struggle to truly understand their numbers. Sure, most know their top line and…

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