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.
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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.
To get past historian Yuval Noah Harari's guarded media persona, Levitt asked why his book *Sapiens* succeeded despite violating a key storytelling rule (lacking characters). This specific, insightful challenge demonstrated deep preparation and prompted a novel, open conversation, breaking through Harari's standard talking points.
Transactional questions get transactional answers. A "story-worthy" question, like "Tell me about the moment you first sensed trouble with your supplier?", prompts a narrative. This approach extracts the emotion, context, and deeper story behind an issue, leading to more authentic connection and insight.
Instead of asking leading questions that corner an interviewee, use open-ended prompts starting with 'how,' 'what,' or 'why.' This encourages expansive answers and genuine information gathering, whereas closed questions allow for simple, uninformative deflections, achieving no learning.
Originating from research with terminally ill children, the 'spill question' (e.g., 'Tell me about X') is a powerful, open-ended prompt. It allows people to reveal their primary concern organically, bypassing the researcher's assumptions about what is important.
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.
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.
To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.
When leading a gratitude circle with teenagers, Matthew McConaughey found generic prompts led to rote answers. He broke the ice by sharing a specific, humorous, and slightly personal point of gratitude, which unlocked authentic and meaningful sharing from the group.