On conducting interviews, handling rejection, and more.

As the founder and host of Design Matters, one of the world’s first and longest running podcasts, has interviewed over 400 artists, designers, and cultural commentators, including Marina Abramovic, Thomas Kail, Laurie Anderson, Milton Glaser, Malcolm Gladwell, and many more. In the 13 years since its inception, the show has garnered over million downloads per year.

Late last year, Debbie spoke at FirstMark’s Design Driven NYC, a monthly event, open to the public, that is the largest monthly creative community of its kind where Design, UX, and Product leaders gather to share new ideas.

We recently caught up with Debbie to hear what she’s learned over the years–both with respect to interviewing leaders and, on a more personal level, what she’s learned about herself.

On One Interview Trend She’s Uncovered:

I’ve noticed that nobody ever really feels successful–that they’ve made it, and that they’re guaranteed to keep making it. I actually just interviewed somebody recently who is one of the most successful performance artists living today and she was talking about how she still experiences doubt all the time and I was shocked.

On the flip side, the only two people I’ve ever interviewed that felt successful as-is were Massimo Vignelli and Milton Glaser, both of whom were in their seventies when I interviewed them. It was like, “Yeah. This is who I am. Take it or leave it.” I truly believe that that is because they have matured into that–I don’t think it was something they were born with.

On The Perfect Questions To Ask:

People ask me all the time now: “How do you conduct an interview? How do you do your research?” To be honest? There really is no magic button that I press…well, other than ‘return’ on a Google search.

The key is that I just ask questions that I really want to know the answers to. I think I’m actually just a really nosy person. I want to know how somebody did something, or made something, or came up with something. If they’re open to being interviewed, then they’re usually pretty generous with their answers. But on that point, I also like to try to respect my guest by not asking the same questions that everybody else has already asked them.

Sometimes that’s tough! How can you talk to somebody that’s won a Grammy, for example, without addressing the fact that they won such a prestigious award like that? What I try to do, in that case, is look at all of their answers that they’ve provided to similar questions elsewhere and then ask follow-up questions about those answers. It’s about going one level deeper.

On Why Connection Is So Important:

I definitely feel a lot of pride when I feel like I’ve done a good podcast–and I know whether or not that’s the case right after the interview. I’ll come out of the studio and think, “ I really connected with that person.”

One of the things that I’ve discovered in my research about how humans interact and connect with each other is that we are happiest when we feel like our brains are harmoniously resonating with someone else’s and we feel understood.

“I’ve realized that we are happiest when we feel like our brains are harmoniously resonating with someone else’s and we feel understood.”

So if I’ve been able to really deeply connect in that way, then I feel like I’m seeing somebody as is, who they are, and they’re seeing the same in me. Those are the interviews where I feel like I’ve really done a good job.

On How She Handles Rejection:

Nowadays, rejection still stings, but I don’t globalize it as much. And I don’t know that it’s because of what I may or may not have accomplished. I think, in many ways, it comes with experiencing lots and lots of rejections and failures. You realize that if you go through enough of them and still manage to come out the other side it doesn’t mean that the rest of your life is doomed.

On The Importance of Metabolizing Your Emotions:

We metabolize all of our emotions–positive and negative. If you allow yourself to feel your emotions, really feel them and not hide or ignore them, then I think they tend to metabolize quicker.

The only feelings we don’t metabolize are the ones we don’t allow ourselves to experience. In that case, they just fester somewhere in the back of your brain. But if you actually go through the emotions head on, it’s sort of like the weather–it’ll pass.

“The only feelings we don’t metabolize are the ones we don’t allow ourselves to experience.”

But you can also run into a problem when you’re only using your achievements as fuel for feeling good about yourself from day to day. We metabolize those feelings of success, too, and then you just need more and can become addicted to it.

It’s really slippery to say to yourself: “I’m gonna base my sense of self, or my happiness quotient on my last achievement.” Because then what happens when you don’t have those things? You can really collapse, and there are times in my life when I felt that way. I put a lot of pressure on myself to be able to achieve. Today, I’m more cognizant of the ephemerality of achievements because the good feelings (like the bad) do dissipate over time and you need to know that it’s inevitable.

On Why To Practice Small Acts of Courage:

One example that I can give you is one of my students, her name is Michelle Poler, did a “100 days” project in my graduate program that was about addressing her fears and that in of itself was her practicing small acts of courage and facing her fears head on. The project went viral. She actually ended up doing a TED Talk. Now, she’s making a living running workshops and giving talks about facing fear.

Never underestimate how these small acts, on a daily basis, can help strengthen your core character and make you more comfortable in all situations.



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