What the best podcasters can teach us about how to have a good conversation

Substantial conversations leave us feeling informed, connected, and inspired. Here’s how you can have more of these discussions in your everyday life.

What the best podcasters can teach us about how to have a good conversation
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Heavyweights such as Adam Grant, Tim Ferriss, Malcolm Gladwell, and Arianna Huffington all have podcasts with huge followings. Why? In part, it’s because the interviews they conduct are generally so compelling. These exchanges leave a strong impression and make us want to listen to the next episode in the series.


These podcasters can teach us a lot about how to engage in successful conversations that move beyond surface-level pleasantries and clichés.

Here are the top five takeaways: 

1. Know your stuff

The best podcasters are extraordinarily well prepared. They talk to experts and read widely.

Adam Grant introduces an array of sources on his podcast. For example, in the episode “The Office Without A**Holes,” he discusses the views of Bob Sutton, author of Assholes: A Field Guide. He interviews Steve Jobs’s biographer Walter Isaacson about Jobs’s “mercurial” personality. He draws upon other sources, including Sheila Heen, coauthor of Difficult Conversations, to show how to deal with annoying people at work. Grant even speaks with a lawyer who admits to being an asshole.

If you want to engage in more substantial conversations, remember that great conversations start with knowledge. Reading widely and thoughtfully will make you well-equipped to bring forward new and unexpected ideas.

2. Be bold in your thinking

Thought leaders are provocative thinkers. They tell you something you didn’t know or challenge beliefs you’ve long accepted. Malcolm Gladwell is an expert at this, of course. In one episode, for example, he disputes the idea that smaller classes lead to better outcomes. By the end of the show, Gladwell’s surprising contention seems remarkably plausible.


What does this mean for you? Conversations with your boss or friends will sparkle and be more productive if you bring forward fresh thinking. The best organizations value people who provide new and exciting ways of approaching problems. No organization can thrive on old ideas.

3. Ask probing questions

The best podcasters create a healthy dialogue by asking great questions.

Tim Ferriss in his podcasts asks a battery of questions that tap into the experience and insights of his interviewees. For example, he asks venture capitalist and author Ben Horowitz how he handled entrepreneurial pressures, to which Horowitz replies: “I’d be up at two in the morning in a cold sweat with my guts boiling. . . . I wasn’t that great at it.”

Ferriss is also creative in asking the unexpected question. He begins his interview with astrophysicist Neil deGrasse Tyson by asking, “Who are some of the people who have influenced or inspired you when it comes to communicating?” DeGrasse Tyson compliments Ferris for hitting a “home run” with that one: “No one has ever asked me that question,” he says.

Asking good questions generates first-rate discussions, whether you’re with colleagues, pals, or your kids. Doing so allows you to build on people’s ideas. It also gives them a great feeling because you care enough to ask what they think. 

4. Let people tell their stories

The best podcasters give lots of airtime to their interviewees. In one episode of her podcast, Arianna Huffington listens to her guest, Ginger Zee, a meteorologist, tell a gripping story about her struggle with mental health. Zee explains how after checking herself into a mental hospital, she immediately wanted to leave, because the place reminded her of the institution in One Flew Over the Cuckoo’s Nest. But she stayed, and there began a path to recovery.


All of us can do more listening, and if we do—whether in company meetings or in casual conversations—we will show generosity toward the people we work and live with.

5. Get the tone right

Finally, the best podcasters know how to strike the right tone—bantering with guests when appropriate and speaking seriously when the subject demands it.

Some use language that pops. Tim Ferriss is great at this. He ad-libs humorously, which helps make his interview subjects feel comfortable. Adam Grant’s language pops because he speaks conversationally, like opting for the word “asshole” instead of the more polite “jerk.”

Arianna Huffington uses the language of empathy in her interview with Ginger Zee. That’s as it should be, since she’s talking with someone about a deeply personal subject. It’s a great reminder that we all need to adjust our language to suit our audience. Every conversation requires words that work for us (and our audience) in building relationships.