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Re:Thinking with Adam GrantHow to get better at interviewing with NYT's Andrew Ross Sorkin | ReThinking with Adam Grant
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At a glance
WHAT IT’S REALLY ABOUT
NYT’s Andrew Ross Sorkin shares interviewing mastery and human insight
- Sorkin argues the interviewer bears primary responsibility for making a conversation work—like an animal trainer who can’t blame the elephant.
- He frames great interviews as a tennis rally: both sides should return hard shots, creating learning and tension rather than one-sided “aces.”
- Preparation is about finding “fault lines” and “speed bumps” (mistakes, critiques, controversies) so tough questions can be asked in ways that keep guests engaged.
- 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).
- 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 ideasTreat 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 quotesYou 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
SPEAKERS
Andrew Ross Sorkin
guestFinancial journalist and interviewer at The New York Times and CNBC, known for interviewing business leaders.
Adam Grant
hostOrganizational psychologist and host of the ReThinking podcast.
High quality AI-generated summary created from speaker-labeled transcript.
