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

Jordan Gross

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.

This question reveals humility. It forces the interviewee to reflect on their life and openly reveal their challenges with a lesson that many people already understand.

For me, being patient and playing the long game has taken me years to understand, and I still struggle with it. But life is a marathon, not a sprint, and we should act accordingly.

2. What common piece of advice do you disagree with?

This is a creative way to ask somebody how they stand out from the rest of the pack. What do they believe that is different from others?

For my response here, I went with Never quit. Sometimes knowing when to quit can actually be more advantageous than sticking with something.

3. What skill do you believe everybody should relearn?

Ryan Holiday shared a quote from Heraclitus: “No man steps in the same river twice. The second time around, both man and river are different than they were before.”

The world changes. We change. It’s important to relearn things. Reread things from time to time because our perspective may change. Our understanding may change between learnings.

I think everyone should relearn how to read at some point in their life. We take it for granted because we’re often so young, but intentionally learning how to read can be a game changer.

4. What uncommon belief do you have that is worth fighting for?

Peter Thiel asks a similar question: “What important truth do very few people agree with you on?”

This question shows what we’re willing to stand up for. It shows what really matters most to us regardless of what others may think.

I believe that we must seek to understand everyone. Every single person. Only then can we make fair and accurate assessments.

5. If an imaginary person saw you when nobody else was watching, what would they say?

This question speaks to one’s character. Who are you behind closed doors? What are you really all about? It‘s also a reminder that we must always be true to ourselves, because that imaginary person might be watching.

I like to believe that this imaginary person sees the same courteous and caring individual that others see. But you’ll have to ask him.

6. What was the most important thing you’ve been taught? What were you like before this? After?

This three-part question unpacks so much about somebody. Who and how were they influenced? Why? What is their willingness to change?

From Dale Carnegie’s How to Win Friends and Influence People, I learned that the best way to interact with others is to focus on them. Before that I loved talking about myself. After, I asked more questions and let them do the talking.

7. What is the highest compliment someone can give you?

This reveals what you truly value about yourself. It shows how you want to be seen.

I just want people to say I’m a good dude. Nothing more complex than that.

8. If you had to give a 30-minute impromptu presentation, what would be your topic?

This is a fancy and fun way to ask someone what they’re passionate and knowledgeable about.

I could talk about sports for hours, but even more so I could talk about my favorite stories. Movies, books, even sports stories, I love sharing through storytelling.

9. What should I ask you now, that I didn’t know to ask before?

This is my favorite closing question I ever received. It gives a chance to share anything that was missed or left uncovered.

Questions for Everyday Life

These questions don’t just have to come out during interviews. You can use them on dates, with friends, or even with family around the dinner table. They’re more creative ways to have deeper conversations.

And as a bonus question, somebody the other day asked me what I have been watching, reading, and listening to. What a person consumes says a lot about them.

Any other questions to add?

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Reimagining Personal Development

New York, NY

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