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

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. 

“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. 

I’m not calling anyone stupid. I’m calling certain questions stupid because of what they do. They don’t help people think. They don’t help them dig. They don’t lead anywhere meaningful.

Smart questions, on the other hand, invite intelligence, openness, and real problem-solving.

What Makes a Question “Stupid” (and What to Ask Instead)

1. It isn’t rooted in genuine curiosity—it’s a statement disguised as a question.
   Example: “Don’t you think that was a bad decision?”
   Better question: “What factors were you weighing when you made that decision?”

2. You answer or steer the question immediately after asking it.
   Example: “What do you want for dinner? I’m thinking Mexican.”
   Better question: “What sounds good for dinner tonight?”

3. It only invites a yes/no response instead of reasoning or perspective.
   Example: “Did you work on the project?”
   Better question: “What progress did you make on the project, and what’s still unclear?”

4. Judgment, criticism, or contempt is baked into the tone.
   Example: “Why would you do it that way?”
   Better question: “Help me understand the thinking behind that approach.”

5. It’s asked to trap, corner, or prove a point rather than understand.
   Example: “So are you saying this failure is my fault?”
   Better question: “What do you think each of us contributed to this outcome?”

6. It’s vague, lazy, or overly broad—forcing the other person to guess what you mean.
   Example: “What’s wrong?”
   Better question: “You seemed frustrated in the meeting—what was going on for you?”

7. It’s driven by fear or the need for control instead of openness and learning.
   Example: “Are you sure this is going to work?”
   Better question: “What risks do you see, and how can we prepare for them?”

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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.

17 Open-Ended Non-Leading Questions

Question 1 - 8

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?

"The ability to ask questions is the greatest resource in learning the truth. - Carl Jung

Question 8 - 17

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?

Want Our Favorite 37 Open-Ended Non-Leading Questions?

Download the 37 Open-Ended, Non-Leading Questions Toolkit and use it to:

• Spark meaningful problem-solving discussions in meetings instead of surface-level updates

• Create accountability by asking questions that invite ownership rather than defensiveness

• Encourage openness and curiosity in everyday conversations at work and at home

• Listen more and talk less, allowing others to think and process out loud

• Uncover root issues instead of chasing symptoms

• Build trust and engagement by asking questions that feel safe and respectful

37 OPEN-ENDED QUESTIONS TOOLKIT

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

There's a big difference between good questions and bad questions. Understanding the difference will enhance how you think, lead, and engage with others.

If you want better answers, you must start by asking better questions. 

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