Worklife with Adam Grant ReThinking: The art of the interview with Andrew Ross Sorkin
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Oct 21, 2025 
Andrew Ross Sorkin, a prominent business journalist and founder of DealBook at The New York Times, shares his insights on engaging interviews with host Adam Grant. They discuss interviewing as a dynamic tennis match and techniques like the four-walls approach to elicit deeper responses. Sorkin reveals how he adapts mid-interview, drawing from a tense exchange with Elon Musk. He also reflects on the psychology of powerful figures and unpacks themes from his book, 1929, analyzing the stock market crash and its lasting psychological impacts.
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Structure Conversations Like A Tennis Match
- Prepare to run a conversation like a tennis match by aiming for long rallies rather than one-sided domination.
- Place thoughtful questions to test the guest and invite them to return the ball to keep listeners engaged.
Identify And Frame Speed Bumps
- Anticipate speed bumps by identifying tough questions or past mistakes before the interview.
- Label difficult questions for guests and frame critiques as third-party quotes to make answers easier.
Use Question Order To Build Leverage
- Order questions to build constraints so guests find it harder to dodge later queries.
- Use sequential questioning to corner someone ethically when seeking a particular truth.
