The last in a series of seven blog posts on interviewing techniques to draw out people’s most authentic stories.

I love asking a speculative question in interviews. These can seem outlandish and a bit crazy, but especially if you’re getting rote responses, they are a great way to shake things up.

Here are some examples.

For a book about cancer, I asked each of 50 interviewees, “If you could turn the clock back and take cancer out of the equation in your life, would you do it?”

For a book about an injured child, I asked her doctors, nurses, teachers, and family, “If you had a crystal ball and could see into Sophie’s future, what do you think you would see? What would you WANT to see?”

The results were astonishing. The very first time I tried this was with a police officer who had been on the scene of a fire in a child care center. Sure, I felt pretty crazy asking a uniformed officer what he would do with a magic wand, but he didn’t blink: he just gave me a beautiful, emotionally nuanced answer that was pure gold.

It’s those moments of connection that make me want to keep asking every obvious, dumb, crazy question I can think of. Sometimes, it makes some magic happen.

If you have enjoyed this blog series on interviewing, let me know in the comments section. And if you would like me to work with you on your interview-based project, email me today on