ReThinking: The art of the interview with Andrew Ross Sorkin

What It Covers

Andrew Ross Sorkin, New York Times DealBook founder and CNBC Squawk Box co-anchor, reveals his interviewing methodology with Adam Grant. Sorkin shares techniques for handling difficult guests, preparing for interviews, and creating productive conversations. He discusses his new book 1929 about the stock market crash and explains psychological patterns among powerful leaders.

Key Questions Answered

• •Tennis match framework: Structure interviews as long rallies where both participants hit the ball hard but ensure the other can return it. Place shots strategically to test capabilities without acing opponents repeatedly. This approach serves the audience rather than pleasing the guest, creating more valuable exchanges than one-sided interrogations where learning opportunities disappear.
• •Four walls technique: Corner evasive subjects by asking sequential questions that each create boundaries, limiting escape routes. Start with foundational questions that establish positions, then build additional constraints through follow-up queries. This boxing-in method works for investigative contexts where direct answers prove difficult to obtain, forcing engagement with uncomfortable topics through logical progression.
• •Speed bump identification: Search the guest's name plus "controversy" in Google before interviews to map potential difficult areas. Share critical quotes from others rather than personal critiques, which removes the interviewer from attack position and acknowledges the guest likely already knows and has considered the criticism, making them more willing to engage substantively.
• •Insecurity drives success: Leaders with extraordinary achievements consistently demonstrate underlying insecurity propelling them forward, whether proving themselves to family members, former doubters, or internal standards. Even those appearing supremely confident at career peaks still ask "Was it good?" after conversations. This pattern persists regardless of accomplishment level, fueling continued mountain-climbing rather than satisfaction.
• •Curiosity decline with power: Successful people often become less curious as they rise, partly because they shift into answer-giving mode as constant question targets. This represents not curiosity loss but suppressed expression. The most admired leaders maintain curiosity about mundane details despite success, while others create bubbles of yes-people or focus inward, losing the questioning habit that initially drove achievement.