10 Tips for Asking Better Questions

Practical insights for using questions for faster learning and stronger relationships

This is a bucket list week for me—on Saturday, I gave a TEDx Talk, Using Questions to Build Real Connection in an Age of Loneliness.

The video will be ready in six to eight weeks, and I’ll certainly share it here! If you want to be among the first to see the video and (if you like it) to help share it with others, please let me know here.

A few days before the talk, I recorded a podcast with Kate Johnson (no relation) of the Comfy Chairs podcast. Conversations with Kate are always engaging, but this episode was special to me. I shared a lot of ideas that are central to my TEDx Talk, and to my way of looking at the world.

You should just listen to the podcast. Find it here for Apple, YouTube, or Spotify.

The episode features some of the best tips on how to ask great questions—and why. I also go deep into the ideas of Appreciative Inquiry, and how to use the methodology’s questions as a “cheat code” to advance your learning and your conversations.

To tide you over until you have time to listen to the podcast, here are 10 ideas, taken from the episode, on how you can ask better questions.

One request:
Hit reply or leave a comment (please) and answer this question—in what situations do you find it most difficult to ask good questions?

1. Ask Questions You Don’t Know the Answer To

The most powerful conversations happen when you venture into uncharted territory. Instead of predictable questions like “How are you?” or “How’s work?” ask something that genuinely surprises you both.

2. Push Beyond Basic Open Questions

Don’t settle for questions that simply avoid yes/no answers. Think of open-to-closed as a continuum and push toward the wider end. Instead of “What’s your favorite book?” try “What makes for a strong character in the stories you love?” The wider you open the question, the more unexpected insights you’ll discover.

3. Frame Questions for the Future

Replace problem-focused questions with solution-oriented ones. Instead of “What didn’t work in last night’s event?“ ask “If we were doing this again, what would we do differently?” This removes defensiveness and puts the focus on the future rather than on placing blame.

4. Show Positive Regard in Your Questions

Your questions should demonstrate respect and assume the best in people. Avoid questions with judgmental undertones. The way you ask matters as much as what you ask—ensure your tone conveys genuine curiosity and respect.

5. Use the High-Point Experience Template

When facing challenges, ask: “Tell me about a specific time when we were at our best around this issue. What happened? Who was involved? What made it possible?” This helps people and teams identify existing strengths and believe in future possibilities.

6. Practice Visualization Through Questions

Ask people to imagine success: “Picture it’s three years from now and we’ve completely solved this challenge. What does success look like? What’s happening? What’s different?” This mental rehearsal is as powerful for teams as it is for athletes.

7. Seek Understanding, Not Just Facts

Ask questions that explore feelings, not just facts. Questions like “What was that experience like for you?” or “How did that feel?” build empathy and deeper connection— which is essential for healthy relationships and addressing conflict.

8. Try Integrative Questions

Spark creative thinking by combining unlike concepts: “How could our onboarding process be more like a party?” or “How should our library be more like Netflix?” These unexpected combinations often generate breakthrough ideas and help your team perform better.

9. Ask for Help Without Shame

Remember that asking questions makes you appear more intelligent, not less. When you say “I need your help,” people think you’re smart enough to recognize their expertise. Embrace questions as demonstrations of wisdom, not admissions of weakness.

10. Follow Up with Reflection Questions

After experiences or conversations, ask yourself: “What did I learn?” or “If I were in charge of that situation, what might I have done differently?” This self-reflection turns every experience into a learning opportunity and builds your leadership capacity over time.

BONUS CONTENT

Remember that questions are fateful—they shape what people focus on and discover.

If you ask someone “Are you tired today?” they’ll scan for fatigue. If you ask “What’s energizing you this week?” they’ll identify sources of energy.

Choose your questions wisely, as they focus attention and shape reality.

And don’t forget to listen to the Comfy Chairs podcast!

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Photo by Magda Ehlers.