Re:Thinking with Adam GrantHow to get better at interviewing with NYT's Andrew Ross Sorkin | ReThinking with Adam Grant
CHAPTERS
- 0:00 – 0:42
Owning the interview: making the “elephant” dance
Sorkin frames interviewing as a host’s responsibility: your job is to make the conversation work, not to blame the guest. Even choosing the wrong guest (“wrong elephant”) is treated as the interviewer’s accountability.
- •Host responsibility is non-negotiable: you can’t blame the guest
- •Sometimes you pick the wrong guest, and that’s still on the host
- •The mindset is radical accountability—"it’s always my fault"
- 0:42 – 1:56
The tennis-match model of great conversation
A strong interview resembles a long tennis rally—dynamic, responsive, and entertaining because both sides return the ball. The goal isn’t to dominate but to create a back-and-forth where each person can respond with substance.
- •Great interviews require a rally, not constant “aces”
- •You want the guest to be able to return the ball
- •Challenge is part of the fun: placement, pace, and responsiveness
- •The interviewer must be ready for the guest to challenge back
- 1:56 – 2:56
Serving the audience, not the guest (and aligning incentives)
Grant and Sorkin agree the interviewer-guest relationship is secondary to serving the audience. Sorkin adds a crucial tactic: persuade the guest that serving the audience is in their own interest, reducing friction.
- •The audience is the primary stakeholder
- •Deprioritize pleasing the guest when it conflicts with viewer value
- •Try to convince guests it benefits them to serve the audience
- •Some guests naturally understand they’re delivering a performance
- 2:56 – 3:47
When a guest won’t play along: tactics and constraints
They discuss what to do when guests don’t “get it,” noting that TV offers structural tools (commercial breaks) while live stages are trickier. The chapter reinforces that adaptability is part of the host’s job.
- •Different environments allow different interventions (TV vs stage)
- •Commercial breaks can reset dynamics on television
- •Live settings require more real-time creativity
- •The host accepts the burden of making it work
- 3:47 – 4:33
Why Sorkin rarely feels satisfied: anxiety, self-critique, and standards
Grant probes Sorkin’s tendency to downplay even excellent interviews. Sorkin describes grading himself on a curve and connects it to his anxious temperament and constant self-evaluation.
- •Even great interviews feel only “pretty good in parts” to him
- •Anxiety shapes preparation and self-assessment
- •High standards drive continuous critique
- •Performance evaluation becomes a habit, not a moment
- 4:33 – 5:47
Preparing for “fault lines”: finding speed bumps and asking hard questions
Sorkin explains his core preparation method: identify a guest’s “fault lines” and “speed bumps” in advance. He outlines ways to ask difficult questions that invite reflection rather than defensiveness.
- •Preparation aims to map fault lines: what drives the person and where tension lives
- •Speed bumps include mistakes, critiques, and uncomfortable topics
- •Mistakes can be framed as audience lessons, making disclosure easier
- •Labeling questions as difficult/complicated can lower defensiveness
- 5:47 – 8:00
Using third-party critiques to depersonalize confrontation
Sorkin recommends reading critical quotes to guests as a way to raise tough issues without making it feel like the interviewer’s personal attack. He notes guests often already know the critique and have considered a response.
- •Read a critical quote to remove “your critique” from the exchange
- •Guests have often seen the criticism and rehearsed their thinking
- •The tactic can increase comfort and credibility
- •It positions the host as moderator rather than aggressor
- 8:00 – 10:04
From friendly chat to truth-seeking: sequencing, “four walls,” and the pilot plan
They explore how question order can progressively limit evasiveness, culminating in the “four walls technique” (cornering via consistency). Sorkin contrasts that precision approach with his usual method: a few destinations and flexibility like a pilot rerouting for weather.
- •Sequencing can box in evasive answers by building consistent commitments
- •Cornering can be necessary to reach certain truths
- •Sorkin typically avoids long lists; he plans destinations, not scripts
- •Precise techniques require exacting structure and control
- 10:04 – 11:07
Notes vs improvisation: when underpreparation backfires
Grant reflects that his best and worst interviews happen with minimal notes: great guests allow improvisation, but assumptions can misfire. Sorkin reframes pride as succeeding with difficult guests—finding a way to reach someone resistant.
- •Few notes can create magic with the right guest and relationship
- •Underpreparation can fail when your theory of interest “doesn’t land”
- •A point of pride is converting a reluctant guest into an engaged one
- •Success often comes from meeting the guest where they are
- 11:07 – 12:39
Case study: Elon Musk and switching gears to prevent a derailment
Sorkin recounts an Elon Musk interview moment that could have spiraled off the rails. He explains how he pivoted away from expected company topics toward Musk’s underlying emotional/psychological “place,” creating depth and regaining control.
- •Early volatility can threaten the entire interview arc
- •The host must detect the moment and adapt quickly
- •Pivoting to motivations and feelings can stabilize the conversation
- •Depth first can unlock room for broader topics later
- 12:39 – 15:05
What job interviews can learn from media interviews (and the “controversy” search)
Sorkin draws parallels between interviewing on-air and interviewing job candidates: both should resemble a fair rally rather than an interrogation designed to make someone fail. He shares a practical prep habit—Googling a leader’s name plus “controversy” to identify speed bumps.
- •Job interviews should simulate real work, not create artificial pressure tests
- •Good interviewers offer candidates chances to show strengths and limits
- •“Where can I place the ball?” becomes an evaluation tool
- •Prep trick: search “[name/company] + controversy” to map fault lines
- 15:05 – 18:40
Self-analysis, perfectionism, and the discomfort of optimization
They discuss Sorkin using ChatGPT for harsh feedback and whether it’s meaningful or a Barnum/Forer-effect mirror. The conversation shifts to perfectionism—over-optimizing life and work—and the wish to feel “enough.”
- •ChatGPT critique can feel insightful but may rely on “truthiness”
- •Sorkin feels aware of flaws but unsure how to fix them
- •The deeper theme is perfectionism, not narcissism
- •Perfectionism mixes ego, contribution, and fear of letting others down
- 18:40 – 24:21
The psychology of power: insecurity and fading curiosity at the top
Sorkin argues many “shoot-the-moon” successful people still feel they have something to prove, driven by insecurity. They debate why curiosity declines with power—yes-men, bubbles, and also constant being asked questions—leading leaders to default to answering instead of asking.
- •Extreme success often coexists with an internal need to prove oneself
- •Insecurity can be healthy fuel or unhealthy pressure
- •Curiosity is common among the best—but can diminish with success
- •Being constantly questioned trains leaders to answer, not inquire
- 24:21 – 33:10
Sorkin’s book ‘1929’: celebrity wealth, leverage, bubbles, and lessons for today
Grant transitions to Sorkin’s book about the 1929 crash, focusing on the characters and motivations behind decisions before and after the collapse. Sorkin highlights revelations: the 1920s popularized get-rich-quick culture, celebrity business figures, easy leverage, and pervasive speculation—while teaching humility about inevitable cycles and the innovation–speculation trade-off.
- •The book emphasizes human drama and incentives around the crash
- •1920s culture amplified celebrity wealth and “get rich quick” thinking
- •Easy credit and margin buying intensified risk-taking and gambling norms
- •Key lessons: humility about inevitable bubbles; preventing runaway excess; innovation often requires speculation
- •Personal scarring effects: his grandfather avoided stocks for life after witnessing the crash
- 33:10 – 37:24
Lightning round and wrap: talking points, hot takes, and feedback on hosting
In a rapid Q&A, Sorkin criticizes rehearsed talking points and argues credibility comes from genuinely grappling with questions. They close with playful opinions (money isn’t emotional armor; nothing good after 8:30), then Sorkin gives Grant an A-minus and reflects on the trade-off between thematic planning and serendipity.
- •Worst interview advice: repeat three talking points instead of answering questions
- •Dream interview subject: Michael Jackson (unpacking choices, feelings, impact)
- •Hot take: money isn’t emotional armor; and “nothing good happens after 8:30”
- •Hosting feedback: A-minus; structure can improve answers but reduces unexpected turns
- •They affirm the value of improvisation and serendipity
