After 200 Podcast Interviews, These 9 Questions Built the Strongest Connection

“Tell me about yourself” wasn’t one of them.

Jordan Gross
Mind Cafe
Published in
4 min readJan 21, 2021

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Photo by Wonderlane on Unsplash

From May 2019 to July 2019 I did 90 podcast interviews in 90 days. I wanted the challenge of setting an audacious goal, and I wanted the thrill of achieving it. But more so than anything, I wanted to learn how to become a better interviewee.

Little did I know, I would end up becoming more invested in the questions people were asking than I was in my responses.

After thousands of minutes on calls, hundreds of zoom invites, and dozens of interviews, I realized the best questions (which led to the best conversations) were the ones that were most specific. The hosts who did their research and crafted a personalized story left a memorable impression on me.

But some questions I received were showstoppers. They had me fumbling over my words, asking if I could take a pause and come back to them. These questions make you stand out as an interviewer and as a human, no matter who it is or in what context you’re speaking.

1. What one lesson has taken you the longest to learn?

An interviewer once asked me this, and then afterward told me she picked it up while listening to Oprah.

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Jordan Gross
Mind Cafe

Son, Grandson | Reimagining Personal Development | “What Happens in Tomorrow World?” Publishing Spring 2021, BenBella Books, Matt Holt Books