Re:Thinking with Adam GrantBrené Brown and Simon Sinek on the leadership skills we need to build | Re:Thinking with Adam Grant
CHAPTERS
- 0:02 – 3:31
Crowdsourcing leadership: who’s “leading” this conversation?
Adam sets up the episode with Brené Brown and Simon Sinek, then playfully calls them out for refusing to choose a topic. The trio frames leadership as service—taking input from others while still being accountable for decisions.
- •Adam introduces Brené and Simon and their leadership influence
- •A comedic debate about “following your lead” vs actually leading
- •Crowdsourcing questions as a leadership move: being in service to the audience
- •Accountability: leaders can take input but must eventually decide
- 3:31 – 6:07
Perspective-taking: naming each other’s core leadership skill
Adam asks each guest to articulate what they think the other believes is the most important leadership skill. Their answers converge on being a good human—vulnerability, trust, connection, service, and teamwork.
- •Simon credits Brené with normalizing vulnerability as leadership strength
- •Brené emphasizes 'who we are is how we lead' (self-awareness, trust, accountability)
- •Brené identifies Simon’s core as trust and human connection
- •Simon reframes 'Start with Why' as service, not goals or self-interest
- 6:07 – 7:18
Leadership is a team sport (and the myth of the self-made leader)
Simon expands on the idea that leadership is cooperative and never accomplished alone. He challenges the ego-driven narrative that leaders “earned” their authority single-handedly.
- •Cooperation as a foundational leadership requirement
- •Good leaders recognize teams that make them successful
- •Ambition is fine, but entitlement undermines leadership
- •Spotlight vs reality: unseen contributors enable outcomes
- 7:18 – 10:43
Thinking out loud without derailing the room
After a brief technical hiccup, the conversation shifts to a subtle leadership challenge: leaders’ offhand comments can become organizational directives. They discuss tactics to create space for others while making it clear when ideas are provisional.
- •Simon’s tactic: physically leaving meetings to avoid dominating
- •“Extroverted thinker” vs extrovert; thinking aloud can be misread as decisions
- •Leaders must label brainstorming: “I’m thinking out loud here”
- •Adam’s Rubin/gold story: casual leader remarks can trigger massive effort
- 10:43 – 13:48
Adjusting communication to different thinkers (pace, hands, tone)
They explore how leaders can adapt their speaking patterns to fit the people in the room. Practical tools—like slowing speech by stilling hands—connect physiology to communication effectiveness.
- •Qualifiers help prevent over-interpretation (“spitballing,” “off the top of my head”)
- •Simon’s technique: interlock fingers to slow pace naturally
- •Adam on varying pace and pitch for energy + comprehension
- •Public speaking skills as transferable leadership communication tools
- 13:48 – 16:58
How to teach leadership: practice, language, and brave containers
Adam asks what actually works in leadership development. Brené describes skill-building through practice, scripts, and psychologically courageous environments rather than vague inspiration.
- •Leadership as observable, measurable, teachable skills
- •Practice through real conversations leaders avoid; triads and rehearsal
- •Shared language tools (“Help me understand…”, “The story I’m telling myself…”)
- •Shift from “safe spaces” to brave/courageous spaces; trust as the container
- 16:58 – 22:13
Why leadership training often misses the people who need it most
Adam raises evidence that high performers benefit more from leadership programs than low performers. Simon argues willingness and incentives matter; Brené questions who gets labeled “high potential” and highlights equity dynamics.
- •You can’t train someone who doesn’t want to lead (motivation prerequisite)
- •Incentive structures can nullify leadership training (targets, backstabbing, hoarding)
- •Leadership as a capacity: not everyone wants/should manage people
- •Equity/inclusion: vulnerability can be weaponized; who defines “best” leaders?
- 22:13 – 22:49
Inclusion in micro-moments: who gets seen, heard, and looked at
They connect leadership effectiveness to everyday inclusion behaviors. Adam cites research on leaders’ eye contact driving voice and inclusion, and discusses the challenge of signaling attention in virtual settings.
- •Brené: diverse samples aren’t enough—application must be co-created across lived experiences
- •Key question: who is allowed to be vulnerable in this culture?
- •Adam cites eye-tracking research: leaders’ gaze predicts inclusion/voice
- •Virtual workaround: private chats to invite quieter voices in
- 22:49 – 24:17
Unexpected leadership skills today: courage and being a learner
They begin a “lightning round” from audience questions on modern leadership skills. Simon emphasizes courage; Brené offers the concise framing of “learner over knower.”
- •Human skills once dismissed as weak are now recognized as strengths
- •Courage: admit mistakes, speak truth to power, step into discomfort
- •Brave space as an operating norm (not “safe” by default)
- •“Learner over knower” as a modern leadership stance
- 24:17 – 25:55
Leading when you’re depleted: ask for help, dig under exhaustion
Responding to questions about low motivation and energy, Simon recommends reaching out to a trusted person for support. Brené pushes deeper: exhaustion often masks loneliness, despair, or unmet needs—especially in distributed work.
- •Private, trusted support systems to sustain leaders
- •Brené: identify the real drain beneath “exhaustion”
- •Remote work reduces casual appreciation; contact often happens only when problems arise
- •Loneliness and lack of team cohesion as emerging drivers of burnout
- 25:55 – 30:40
Service vs martyrdom: boundaries, control, and ‘weaponized’ servant leadership
They tackle how to serve others without neglecting yourself. Brené reframes “too much empathy” as enmeshment/caretaking, stresses boundaries, and warns that helping can be a form of control; Simon distinguishes service from martyrdom.
- •Empathy has limits by definition; beyond that it becomes enmeshment/caretaking
- •You can’t give what you don’t have: boundaries are leadership, not selfishness
- •“Help is the sunny side of control” (Anne Lamott): over-helping can be control
- •Pathological altruism: helping as validation/approval-seeking; servant leadership can be weaponized
- 30:40 – 33:17
When to step down—and why some people don’t want leadership at all
They answer when leaders should leave roles and why younger generations may avoid senior leadership. The discussion normalizes opting out, urges better leadership design, and critiques outdated promotion-centric career models.
- •Humility to recognize your limits: I can take the org from A→B, not to C
- •Signal to step down: work becomes self-focused rather than other-focused
- •Younger workers may “work to live,” not climb; still can be great contributors
- •Make leadership more human-centered and inclusive to increase willingness
- 33:17 – 36:27
Reframing leadership language—and managing up with difficult feedback
They play with alternatives to the word “leadership,” rejecting paternalistic “parent” metaphors and favoring coach/facilitator. They then address managing up: lead where you are, use effective confrontation, and model vulnerability to unlock receptivity.
- •Alternatives: ‘facilitator’ (Brené) and ‘coach’ (group consensus)
- •Avoid family/parent metaphors at work; resist paternalism
- •Managing up: be the leader you wish you had; use effective confrontation
- •Model vulnerability to shift leaders from ego-threat to care and responsibility
- 36:27 – 40:34
Leadership isn’t a fixed ‘style’: care and connection are non-negotiable
They close by challenging the idea that leaders can hide behind “that’s not my style.” Simon argues leaders must adjust to be heard and understood; Brené emphasizes that care and connection are irreducible prerequisites—and if they’re missing, restructure reporting relationships.
- •Leaders should be students of leadership, not self-declared experts
- •Self-awareness doesn’t excuse harmful behavior (“I’m an asshole, that’s who I am”)
- •Research insight: care for and connection with people you lead is the baseline
- •If deep affection/care isn’t possible, reassign support/reporting to someone who can provide it
