To get past the rehearsed answers of country music stars, author Mike Perry started asking an unexpected question: "Tell me about your bus driver." This peripheral query broke the script, prompting genuine, hour-long conversations and revealing far more than the standard questions ever could. It's a powerful journalistic technique.

To prevent guests from adopting a rehearsed, "idealized" persona, the podcast host starts recording as soon as they sit down. By eliminating formal cues like "Are you ready?", the conversation feels natural and unplanned, leading to more honest and unguarded responses that reflect the guest's true personality.

The best interviews aren't about one person dominating. They're like a long tennis rally where both participants hit the ball hard but aim to keep the conversation going, creating a more engaging and insightful exchange for the audience.

Citing Oprah Winfrey, Rubenstein argues the key to great interviewing is not having the best questions but being a great listener. True listening allows the interviewer to pivot and follow up on unexpected answers, turning a rigid Q&A into a genuine conversation that uncovers far deeper insights than a prepared script ever could.

Asking questions that probe values, beliefs, or experiences—"deep questions"—can create surprisingly intimate connections in seconds, even with strangers like a barista. These questions invite authenticity and move beyond superficial small talk, making the other person feel seen and valued.

Building deep connections isn't just about asking probing questions; it's about reciprocal vulnerability. Super-communicators often volunteer personal information about themselves first. This signals safety and gives the other person implicit permission to share something equally intimate, creating a powerful bond.

Knowing his podcast audience was audio-only, Steve Levitt intentionally avoided asking guest BJ Miller about the accident that caused his amputations. This forced a conversation about Miller's work, not his trauma. When the story was finally told late in the interview, it emerged with more authentic emotion than in typical settings.

Andy Richter's technique for better interviews is to start recording the moment a guest arrives. This captures unguarded conversation before the formal "commercial vessel" of the show begins. Avoiding a stilted intro maintains a framework of real human interaction, leading to more authentic content.

Unlike traditional media's short, confrontational interviews, long-form podcasts allow public figures to have extended, nuanced conversations (e.g., three hours on Joe Rogan). This reveals a more human side and can significantly shift public perception.