How to Transform Stupid Questions
The future is built by the curious.
Stupid questions are easy to turn into smart opportunities. Notice the following examples.
“Don’t you think it would be better if…?” Or “What are some other options?”
“Why did you do it that way?” Or “What didn’t happen that caused this failure?”
“What were you thinking?” Or “What would you do differently next time?”
“Are you sure that’s a good idea?” Or “What makes you believe that will work?”
“Why didn’t you come to me sooner?” Or “What needs to be in place for you to be comfortable coming to me sooner next time?”
4 Ways to Ask Powerful Questions
#1 Touch Imagination
- What would it look like if you hit a home run this week?
- Where would you go if you cut the sandbags from your balloon?
- How might you navigate stormy seas ahead?
#2 Use Action Words
- What did you do that made this come together?
- What will you do next? What makes you think that will work?
#3 Add Time
- When will you try that?
- What worked last time? What didn’t?
- What’s next for you?
- If you wait, what’s at risk?
#4 Shift Perspective
- What would you do if you were the CEO? The customer?
- What might your colleagues suggest?
- What challenges are your direct reports facing that you’re not seeing?
Challenge
Is your curiosity closed, open, or something in between? Don’t use verbs like “Wouldn’t it be good if you…”
Don’t use curiosity to give advice. Open questions begin with what, how, who, or when.
Consider tone. Is your curiosity filled with doubt or optimism? The spirit behind curiosity shapes the response you receive.
Commit to asking two questions before making one statement.
What are some stupid questions?
What guiding principle for curiosity can you add?
Powerful Questions Produce Results
7 Questions You Can Use to Help Anyone Develop, Even the Boss
The Art of Asking Great Questions HBR





I think these sort of questions have become so abnormal in everyday work life that the questioned will believe the questioner is being passive-aggressive 🙂 I love the advice to use “who, what, where, and how” to put a sort of safety net around our tendency to be advising rather than curious. Thanks Dan.
Thanks for your insight, Matt. You bring up the importance of being trustworthy. It’s important that others believe you have their best interest at heart. The other thing that you bring to mind is the problem of asking questions that lead to the answer we want. That feels like manipulation.
I only have one employee, and at the moment she’s part time. But I have always said to her, feel free to question everything I do, or our small business does. Ask lots of questions. I’ll tell you if I don’t know, and we can figure out the answers together.
And if you think I’m making a mistake, or that I’m leading the business down the wrong path, speak up. I may not always agree, and I do have the final say, but present your case and give me something to think about. Challenge me to think deeper.
And yep- there’s no such thing as a stupid question – unless it’s one you don’t ask.
Thanks, Paul. Being open to curiosity is a powerful indication that we value and respect people. Let’s face it, when people feel valued they’re more likely to flourish at work.
I was good until I got to the last bullet on question 4, “What challenges are your direct reports facing that you’re not seeing?” If the supervisor isn’t seeing the challenges; how would they be expected to answer such a question. It would seem that this question is a little too open ended. Maybe, “What are you hearing from the troops?” would be a better question.
Ha. Good point. You’re right, the phrasing is tricky. The intent behind question is to spark curiosity. It’s about prompting leaders to pause and consider: “What might I be missing?” or “What signals am I overlooking?”
That said, your suggestion, “What are you hearing from the troops?” is concrete and actionable and helps. Thanks Cliff.
Take the time to learn and practice Appreciative Inquiry techniques.
Don’t burn people who share important information with you. Be ethical in your handling of the answers and the people who shared them with you, so nobody gets hurt by doing so. Show discretion and protect the people who cared enough to give you information. Or you’ll never learn anything from anyone ever again. Employees may even give you bad information on purpose. Especially when they are lower in the organizational hierarchy than yourself and have less authority & power. Give credit where it’s due for good ideas, but never sabotage anyone who shared something sensitive, private, or confidential with you. Think before you blab.