20 Interview Questions that Guarantee a Compelling Story

Award-winning writer Kathy Widenhouse has helped hundreds of nonprofits and writers produce successful content and has gained 600K+ views for her writing tutorials. She is the author of 9 books. See more of Kathy’s content here.

Updated 10.29.24

Good interview questions are not a mining expedition, but rather a conversation with a caring friend. People like telling their story, especially if you show empathy with them. When you ask and then listen, you build trust.

It’s the person behind the facts that makes a compelling story.

So when you ask interview questions that dig deeper, you’ll go beyond the facts to reveal personal struggle, conflict and victory.

These kinds of real-life stories are a powerful tool.

Try these interview questions to help the storyteller reveal the heart and soul behind the tale.

Questions to get started

1. Describe where you were when [event].

2. What circumstances led you to [event]?

3. What did you do when [event]?

Questions about people involved

4. Who else was involved?

5. In what ways did those involved help you/ create challenges for you?

6. How did your friends and family react?

7. Describe why [relationship] was so meaningful to you during [event].

Questions that go deeper

8. What did you do next?

9. How did you decide to [action]?

10. Tell me the biggest reason you [action].

11. How did that work for you?

Questions that pull out a life lesson

12. What was the most significant moment during [event]?

13. At what point did you realize [situation]?

14. In what way (ways) are you a different person today because of [event]?

15. How has this experience impacted the decisions you make today?

16. Name the top two or three lessons you learned from your experience.

17. What would you say to others who find themselves in a situation similar to yours?

Questions that tie story to your organization

18. How did you find out about [organization]?

19. Why are you willing to share about your experience?

20. How does your experience reveal what [organization] is all about?

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