Dr. Jane Goodall and Cal Fussman — The Tim Ferriss Show

The Art of Asking (and Telling): A Deep Dive into the Power of Questions with Cal Fussman

Cal Fussman is a New York Times bestselling author, writer at large at Esquire International, speaker, and host of the "Big Questions with Cal Fussman" podcast. In this episode, he shares his unique perspective on the art of interviewing, discussing how his interviewing style has evolved over decades and offering valuable insights into how to ask powerful questions that unlock deeper truths.

Core Concepts and Philosophies

Fussman believes in the power of "aiming for the heart, not the head" when asking questions. This approach, which he honed through years of traveling and interviewing people from all walks of life, seeks to uncover the emotional core of a person's story, leading to more profound and memorable insights.

Practical Strategies and Advice

• Embrace the power of the first question: Fussman argues that the initial question can set the tone for the entire interview. Aim for a question that goes straight to the heart of the matter, prompting the interviewee to reflect on their experiences and personal truths. He uses the example of his interview with Mikhail Gorbachev, where his question about the best lesson his father ever taught him unlocked a deeply personal story about the former Soviet leader's childhood and his perspective on peace.
• Embrace the unexpected: Fussman encourages a non-linear approach to interviewing, emphasizing the importance of being open to the unexpected turns of conversation. His story of traveling around the world and being invited to stay with people he met on buses and trains illustrates how embracing the unplanned can lead to surprising encounters and deeper connections.
• The "good stuff sticks": Fussman argues that truly powerful moments are often the ones that resonate most deeply. He uses the analogy of wine, suggesting that great moments, like great wines, are best enjoyed when they've had time to mature and develop their full flavor. By remembering those moments that resonated with him, he can draw upon those experiences to tell more compelling stories.
• Don't be afraid to be vulnerable: Fussman acknowledges that everyone has their own insecurities and struggles. By being open about his own experiences, he creates a more relatable and authentic connection with his audience. His story about being self-conscious about his interviewing style, and his anecdote about walking past a beautiful woman on a train because he didn't feel "handsome" enough, illustrates how being vulnerable can build trust and create more impactful conversations.

Supporting Evidence

Fussman frequently references his own experiences, providing anecdotal evidence for his strategies. He cites examples from his interviews with prominent figures like Mikhail Gorbachev, Donald Trump, and George Foreman to highlight how certain questions can unlock deeper insights and personal stories.

Personal Application

Fussman's approach to interviewing is deeply personal. He describes how his travels and encounters with diverse individuals have shaped his understanding of human nature and the power of storytelling. He applies the principles he shares by being present and attentive to his subjects, allowing them to guide the conversation and revealing their stories in their own words.

Recommendations for Tools and Techniques

Fussman doesn't explicitly recommend any specific tools, but he emphasizes the importance of being present and attentive. He encourages listeners to be curious, open-minded, and willing to embrace the unexpected. His advice to simply "write" for aspiring writers suggests that the best tool for cultivating one's voice is consistent practice and engagement with the craft.