16 Dumb Questions You’re Afraid to Ask


The hardest question to ask is the obvious one. Fearful leaders remain silent. Courageous leaders ask.

  1. What are we doing?
  2. Compared to what?
  3. Who said?
  4. Why not? Move from “either/or” to “and” by asking, “Why not?”
  5. What problem are we solving?
  6. What’s working? How? Why?
  7. Begin agenda items by asking, “What questions should we ask?”
  8. What are our values? When employees cut themselves, values should come out.
  9. Which of our values is driving this decision? How?
  10. Where are we going?
  11. Who are we?
  12. How does this take us where we want to go?
  13. Who is our customer?
  14. What value do we deliver?
  15. How are we communicating our value to customers? Unperceived value isn’t valuable.
  16. How am I doing?

Bonus: What are we afraid to ask?


The best way to challenge the status quo is with questions. Dumb questions test basic assumptions. But, fear of looking dumb makes us ignorant.

“It is not the answer that enlightens, but the question,” Decouvertes.

When you think you know, assume you don’t.

Questions create confusion initially
and end confusion eventually.

Bonus tip #1: Ask questions that lead to action. Knowledge emerges when people take uncertain action.

Bonus tip #2: Always follow questions with silence.

Interested in more: Read Facebook responses to: “Leaders should ask stupid questions like _______.”

How have dumb questions helped you?

What dumb question can you suggest?