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The art of the interview with Andrew Ross Sorkin

The art of the interview with Andrew Ross Sorkin

ReThinking · Oct 21, 2025

Master interviewer Andrew Ross Sorkin on the art of conversation, the insecurity driving success, and cautionary lessons from the 1929 crash.

Frame Great Conversations as a Tennis Match, Not an Ace-Serving Contest

The best interviews aren't about one person dominating. They're like a long tennis rally where both participants hit the ball hard but aim to keep the conversation going, creating a more engaging and insightful exchange for the audience.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago

Great Hosts Act Like Animal Trainers: It's Always Their Job to Make the Elephant Dance

A host or interviewer can never blame a difficult guest for a bad interview. They must take full responsibility for the outcome, even if it means they "picked the wrong elephant." The burden of creating an engaging conversation always falls on the host.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago

Structure Job Interviews as a Collaborative Tennis Match, Not an Interrogation

Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago

Even 'Shoot the Moon' Success Is Often Fueled by Deep-Seated Insecurity

The most accomplished people often don't feel they've "made it." Their immense drive is propelled by a persistent feeling that they still have something to prove, often stemming from a past slight or an internal insecurity. This is a constant motivator that keeps them climbing.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago

Ask Tough Questions by Quoting External Critiques to Disarm Defensiveness

Instead of personally challenging a guest, read a critical quote about them from another source. This reframes you as a neutral moderator giving them a chance to respond, rather than an attacker. The guest has likely already prepared an answer for known criticisms.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago

Financial Speculation Is the Necessary, Inseparable Twin of True Innovation

Innovation doesn't happen without risk-taking. What we call speculation is the essential fuel that allows groundbreaking ideas, like those of Elon Musk, to get funded and developed. While dangerous, attempting to eliminate speculative bubbles entirely would also stifle world-changing progress.

The art of the interview with Andrew Ross Sorkin thumbnail

The art of the interview with Andrew Ross Sorkin

ReThinking·4 months ago