You’ve talked to every design mastermind out there. How do you prepare and present your questions to get the most interesting answers?

I am endlessly fascinated by the trajectory of a person’s life, the choices they make, how they overcome obstacles or handle success and how they essentially become who they are. Meeting and talking to the most interesting people in the industry (and beyond) has been the greatest gift of my life. I think that passion comes through in the way I interview people.

In terms of preparation, I usually spend about 10 hours researching for every one hour of actual interviewing. But I LOVE researching my guests, so it doesn’t feel laborious or like a chore. I try to read anything public they’ve written (blog posts, books, etc), watch their online talks or lectures, and read every interview they’ve ever conducted, if possible.

I usually cull about 20-25 pages of research from my findings, and then whittle the research down to about 5-7 pages of questions about numerous aspects of their lives. I want to be able to pivot if my guest takes the interview in a different direction than I expect or intend. I often say that a good interview is like a good game of pool: you don’t try to shoot one ball in one hole. You want to shoot one ball in one hole but also leave enough the balls on the table in position to successfully shoot the next ball.