Ask All the Challenging Questions

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

[When a guest is hesitant], I say, hey, our listeners will like you more, will identify with you more, and I promise will be moved by what you say if you can try and reach into your mind, soul, whatever, your past. And open up. And do kind of a trust fall.

—Guy Raz, presenter of the “How I Built This” podcast

One of my very favorite interviewers right now is Guy Raz. He epitomizes the kind of interviewing that I love to do: he draws out people’s stories by being totally engaged in what they are telling him. He encourages them to be vulnerable, sharing their failures as well as their triumphs. You never get the feeling that he is setting out to trap his guests into saying more than they feel comfortable with.

“You know the trust fall side of it is hard,” Raz said. “But I’ve been doing this for twenty years and many of the people I interview have been listening to me for a while, so I’m lucky in that a lot of them know and can trust that I will treat their story with respect, fairness, and sensitivity.”

If you regularly interview high-profile executives, at some point you’ll receive a bland, vanilla answer, or a guarded one from your guest. When this happens, Raz works around the canned answer to get a deeper insight, by re-phrasing the question and not giving up.

“I’m very persistent. I often say to people, I know you’ve been asked this question but I’m asking it in a slightly different way because I think there’s a different answer here. I’m very straightforward with people. I’m not trying to trick them.”

In the next post, find out how the words you choose can make all the difference between getting a great answer and making your guest walk out.