Skip to content
Re:Thinking with Adam GrantRe:Thinking with Adam Grant

How to get better at interviewing with NYT's Andrew Ross Sorkin | ReThinking with Adam Grant

As a business journalist, Andrew Ross Sorkin writes for the New York Times DealBook, which he founded, and co-anchors Squawk Box on CNBC. In this episode, Adam and Andrew riff on what makes a great conversation and compare notes on their best and worst interviews—including when Elon Musk told Bob Iger to f*** off. They also investigate what Andrew has learned about the psychology of powerful people and explore surprising insights from his new book, 1929, on the infamous stock market crash. Follow Host: Adam Grant (Instagram: @adamgrant | LinkedIn: @adammgrant | Website: https://adamgrant.net/) Guest: Andrew Ross Sorkin (Instagram: @sorkinsays | Website: https://www.andrewrosssorkin.com/) Links Book: https://sites.prh.com/1929 Join us in person at a TED conference: https://tedtalks.social/events Become a TED Member to support our mission: https://ted.com/membership Subscribe to a TED newsletter: https://ted.com/newsletters Follow TED! X: https://www.twitter.com/TEDTalks Instagram: https://www.instagram.com/ted Facebook: https://facebook.com/TED LinkedIn: https://www.linkedin.com/company/ted-conferences TikTok: https://www.tiktok.com/@tedtoks Podcasts: https://www.ted.com/podcasts The TED Audio Collective is a collection of podcasts for the curious. The TED Audio Collective videos may be used for non-commercial purposes under a Creative Commons License, Attribution–Non Commercial–No Derivatives (or the CC BY – NC – ND 4.0 International) and in accordance with our TED Talks Usage Policy (https://www.ted.com/about/our-organiz...). For more information on using TED for commercial purposes (e.g. employee learning, in a film or online course), please submit a Media Request at https://media-requests.ted.com.

Andrew Ross SorkinguestAdam Granthost
Oct 24, 202537mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

NYT’s Andrew Ross Sorkin shares interviewing mastery and human insight

  1. Sorkin argues the interviewer bears primary responsibility for making a conversation work—like an animal trainer who can’t blame the elephant.
  2. He frames great interviews as a tennis rally: both sides should return hard shots, creating learning and tension rather than one-sided “aces.”
  3. Preparation is about finding “fault lines” and “speed bumps” (mistakes, critiques, controversies) so tough questions can be asked in ways that keep guests engaged.
  4. They discuss techniques for difficult questioning—using third-party critical quotes, labeling questions as hard, and sequencing questions to prevent evasion (the “four walls” approach).
  5. The conversation expands into Sorkin’s book on the 1929 crash, emphasizing how get-rich-quick celebrity capitalism, leverage, and human psychology fuel bubbles—and why humility and speculation-for-innovation must be balanced.

IDEAS WORTH REMEMBERING

5 ideas

Treat the interview outcome as the host’s responsibility.

Sorkin’s “elephant” metaphor insists you can’t blame an unresponsive guest; if the conversation fails, it’s often due to preparation, framing, or guest selection.

Aim for a ‘tennis rally,’ not a highlight reel of aces.

A great interview challenges the guest with well-placed shots while still making it possible—and compelling—for them to return the ball, creating back-and-forth learning.

Prepare by mapping ‘fault lines’ before you step onstage.

Sorkin looks for the topics that create friction—mistakes, critiques, sensitive decisions—so he can either navigate around them or cross them collaboratively with the guest.

Use third-party critiques to ask hard questions without sounding accusatory.

Reading a critical quote shifts the critique from “you vs. me” to “let’s respond to what’s already out there,” and guests often have a prepared, thoughtful answer because they’ve seen it.

Name the difficulty of a question to reduce defensiveness.

Prefacing with “this is complicated” signals empathy and invites joint problem-solving, making it easier to discuss uncomfortable topics without derailing.

WORDS WORTH SAVING

5 quotes

You are like an animal trainer. It is your job to make the elephant dance, and you can never blame the elephant.

— Andrew Ross Sorkin

I'm rooting for a long, long match. That's what I want, and I think that's what everybody wants.

— Andrew Ross Sorkin

The worst advice people get when they're being interviewed is to show up with those three points- that they're supposed to repeat over and over and over again.

— Andrew Ross Sorkin

Look, all I'm trying to do when I prepare for an interview is figure out where the fault lines are. That's literally what I'm always trying to do.

— Andrew Ross Sorkin

Money is not emotional armor.

— Andrew Ross Sorkin

Interviewer accountability (“make the elephant dance”)Tennis-match model of dialogueServing the audience vs pleasing the guestSpeed bumps, fault lines, and prep routinesHandling critiques with third-party quotesQuestion sequencing / “four walls” technique1929 crash psychology: leverage, bubbles, humility, speculation

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

iOSAndroidClaudeChrome