Podcast Interviews

My conversations with some great podcast hosts on the power of questioning

I’ve been a guest on a lot of podcasts over the past few years. Some of the podcasts end up reaching many people; others, not so much. But the conversations are invariably interesting and I learn as much from the hosts as they do from me.

Below is a sampling of some of my favorite podcast conversations.

The Knowledge Project logo

“The Knowledge Project” podcast, with Shane Parrish

Shane is the creator of the terrific Farnham Street blog and a longtime contributor at Time magazine. His hit podcast, The Knowledge Project, is about all things related to creativity, lifelong learning, decision-making, and critical thinking. We had a rich, wide-ranging conversation, during which Shane dug into my creative work habits: how I try to cut myself off from distractions; sources of inspiration; productivity tips. He also did a particularly good job of dissecting and exploring my Why/What If/How framework for innovative questioning.

Motley Fool’s “Rule Breaker Investing” podcast, with David Gardner

David Gardner is a legend in the world of finance—he co-founded Motley Fool, the groundbreaking investment advice company. But Gardner is also a highly curious man whose interests range far and wide. In this conversation, David and I talk only a bit about finance (luckily for me) and a lot about how curiosity and questioning can enrich one’s career and life.

The Learning Leader logo

“The Learning Leader” podcast, with Ryan Hawk

On his show, Ryan has interviewed hundreds of leadership experts like Tony Robbins and Marshall Goldsmith. Ryan and I talked about the benefits and challenges of being a “questioning leader,” including an interesting exchange on why today’s leaders must “have the confidence to be humble.”

Art of Manliness podcast logo

“The Art of Manliness” podcast, with Brett McKay

How could I resist going on a show with a title like that? And a show whose logo is an illustration of a bare-chested Hemingway-ish figure in a boxing stance? Actually, this podcast hosted by Brett McKay is so popular it’s in the top 1% of all Spotify podcasts. In this episode, Brett and I talked about how a questioning mindset can enable you to embrace challenges, strengthen relationships, and even help you when you’re out on a date!

“Soul Force Politics” podcast, with Heather Mizeur

Heather is a Maryland-based politician and activist, who hosts a podcast about culture, politics, and social justice. She traveled to my little office in Mount Kisco, New York, where she set up her broadcast equipment and then engaged me in a wonderful conversation that looked at questioning from a whole different angle—a more socially-conscious one.

Wonder Rigor Lab podcast logo

“WonderRigor Lab,” with Natalie Nixon

Natalie is a top speaker and a friend whose work focuses on creativity and curiosity—two things I love to talk about. In this episode of her podcast, we dig deep into the mysteries of curiosity: what is it, where does it come from, how can we inspire more of it.

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