ReThinking The art of the interview with Andrew Ross Sorkin
41 snips
Oct 21, 2025 
In this engaging conversation, Andrew Ross Sorkin, a prominent business journalist and founder of DealBook, shares his insights on mastering the art of the interview. He likens interviews to tennis matches, emphasizing the importance of balanced exchanges for audience engagement. Sorkin recounts his experience with Elon Musk, reflecting on how to navigate volatile moments. He also discusses the psychology of influential figures, revealing their insecurities. Finally, he delves into the lessons from his book on the 1929 stock market crash, tying past events to today's financial landscape.
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Play The Long Rally
- Treat interviews like a tennis match where you and the guest keep the rally going for the audience.
- Convince guests it's in their interest to serve the audience so the conversation stays engaging.
Map The Speed Bumps
- Find the "speed bumps" in advance: tough questions, mistakes, or critiques the guest has faced.
- Read a critical quote to them to depersonalize hard questions and invite a prepared response.
Corner With Care
- Use ordered questions to limit evasions and lead guests into harder answers (the "four walls" technique).
- Plan your interview arc but remain ready to shift when the conversation's "weather" changes.