Yes, There Are Stupid Questions (Let’s Talk About Why)

“There’s a phrase we hear all the time: ‘There are no stupid questions.’ 

I get why people say it. It’s meant to encourage curiosity and make people feel safe. But here’s the problem—I don’t believe it’s true. 

In my work with leaders, teams, couples, and families, I’ve seen that some questions don’t create clarity at all. They create confusion. Some questions don’t move us forward—they keep us stuck. And some questions quietly protect our comfort, our ego, or our fear, while pretending to be curiosity. 

Great questions come from genuine curiosity, not from trying to push someone toward a certain answer. They are open-ended, inviting thoughtful responses instead of simple “yes” or “no” replies, and they are non-leading, allowing people to share their perspective freely without being steered in a specific direction.

Try starting with words like “what” or “how,” and follow up with prompts like “tell me more” or “can you give me an example?” Ask because you want to understand their perspective—not to fix, change, or convince. And remember, how you ask matters just as much as what you ask. A calm tone, open body language, and patience go a long way in helping someone feel safe enough to openly share.

37 Open-Ended Non-Leading Questions

Question 1 - 22

1. What do you want?
2. What makes this important?
3. What’s the history of this issue?
4. How have you successfully handled something similar?
5. What is the core issue for you and/or your team?
6. What help do you need? Who can help you?
7. What does success look like? (i.e., what does a home run look like?)
8. What’s the biggest challenge?
9. How would you handle this differently if failure were not an option?
10. What are we trying to accomplish?
11. What’s the most important priority to you?
12. What do your colleagues see as the main challenge here?
13. What are you up against?
14. What’s the biggest challenge you’re facing?
15. How can you overcome that challenge?
16. What happens if you do nothing?
17. Can you give me an example?
18. How does this resonate with you?
19. How are you going to get there?
20. What is the most reasonable next step to make progress?
21. What are you most afraid of happening? How would you handle that?
22. What would you do if you were 10 times bolder? 23. What strengths can help you here?

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Questions 24 - 37

24. How does this align with your core values?
25. What’s a goal you can set with this?
26. How are you stuck with this issue? How can you get unstuck?
27. What tough decision might you be putting off? 28. Talk us through ...
29. Can you tell me more?
30. What’s an example?
31. What did you learn from this experience?
32. What would you do differently next time?
33. How can I help?
35. What advice would you give to a close friend with this same issue?
36. What ideas do you have?
37. What would you do if you were 10 times more confident?

The quality of your life, your leadership, and your relationships is directly tied to having courageous conversations. And courageous conversations occur when you ask courageous, high-quality questions. 

If this was helpful, SUBSCRIBE TODAY and get instant access to my free video and worksheet: Shatterproof Yourself — 7 Small Steps to a Giant Leap in Your Confidence.

There is a big difference between good questions and bad questions. Understanding the difference will enhance how you think, lead, and engage with others. Because if you want better answers, you must start by asking better questions. 

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