Simon SinekThe Leadership Advice Nobody Follows (But Everyone Should) from Top Leadership Expert
CHAPTERS
Appreciation as a Leadership Practice: “What You Look For, You Find”
Don Yaeger opens with a practical mindset shift: intentionally look for what people are doing right. Simon and Don explore how appreciation, recognition, and curiosity change what you notice—and therefore what you reinforce—in relationships and at work.
- •Deliberately scan for effort, care, and “extra mile” behavior
- •Recognition creates more of the behavior you want to see
- •Negativity bias: if you hunt for mistakes, you’ll keep finding them
- •Appreciation is a practice, not a personality trait
- •Leadership starts with attention—what you choose to notice
Don Yaeger’s Origin Story: Curiosity, Journalism, and Learning to Tell Stories
Don traces his early love of news and storytelling—from delivering Stars and Stripes in Japan to recording his own commentary at age 11. He outlines his path through newspapers and into Sports Illustrated, where he learned elite-level narrative craft.
- •Early habit: consuming news and forming opinions as a child
- •Journalism as a vehicle for curiosity and learning
- •Career progression: local papers → politics editor → Sports Illustrated
- •Being surrounded by great writers sharpened his storytelling ability
- •Storytelling is a learnable craft built through reps and observation
Meeting John Wooden: Why the Winningest Coach Wasn’t Obsessed With Winning
Don explains how Sports Illustrated led to meeting John Wooden and why Wooden matters even beyond basketball. They unpack the apparent paradox: Wooden achieved historic results by focusing on relationships, standards, and development rather than outcomes.
- •Wooden’s record: 10 NCAA championships, including a dominant run
- •Success in college required constant development due to player turnover
- •Wooden adapted his system to the players he had—not vice versa
- •He believed performance is driven by relationship and mindset
- •Outcome obsession is not the same as excellence obsession
The Pyramid of Success: Standards of Being Over Standards of Performance
Wooden’s “Pyramid of Success” becomes a framework for human excellence: industriousness, team-first behavior, and character. The conversation emphasizes that Wooden coached the person to elevate the team, trusting that results would follow.
- •Pyramid of Success as a blueprint for building greatness
- •Greatness is built through habits and character, not declared
- •Focus: being great teammates rather than chasing “champion” status
- •Servant leadership applied even to star players
- •Team culture as the true competitive advantage
Ego, Accountability, and Team-First Rituals: The Bill Walton Haircut Story
A vivid example shows how Wooden handled superstar ego with consistent standards and clear reasoning. Don also shares Wooden’s ritualized behaviors—like thanking the passer—that trained humility and recognition into the team’s identity.
- •One standard for everyone: best player to worst player
- •Bill Walton tests the rule; Wooden responds: “We’ll miss you”
- •Rules had rationale (availability, health, responsibility to teammates)
- •Mandatory gratitude ritual: point and thank the assister
- •Culture is shaped by repeated, explicit behaviors—not slogans
A 12-Year Mentorship: Showing Up Prepared and Proving You Applied the Lesson
Don describes a rigorous mentorship cadence with Wooden: every other month for 12 years, Don drove the agenda and had to demonstrate real-life application. Mentorship is framed as transformation, not access or admiration.
- •Mentorship sessions required preparation and accountability
- •Don had to report: what he learned, how he used it, how he improved
- •Wooden demanded the relationship produce change—not wasted time
- •Mentorship aimed at becoming better across life roles (spouse, parent, leader)
- •Real mentorship is effortful for the mentee, not passive consumption
Wooden’s Love Letters and the Regret of Waiting to Say What Matters
Don recounts Wooden’s monthly love-letter ritual after his wife’s death and the haunting line: he wished he’d said “all of it” while she was alive. The story becomes a leadership and relationship lesson about expressing appreciation now, not later.
- •Wooden wrote a love letter every month on the 21st for 25 years
- •Ritual: write, seal, place on her pillow, archive the previous letter
- •Lesson: we often praise others but forget our closest relationships
- •Core insight: don’t assume time—say the meaningful thing now
- •Grief reveals priorities; leaders can learn without needing the loss
Turning Appreciation into a System: Don’s 52 Letters and the Attention Habit
Inspired by Wooden, Don creates a weekly letter practice for his wife—hundreds of letters over many years. They discuss how the habit forces you to search for good, crowding out petty resentments and strengthening connection through sustained attention.
- •Don gifts 52 letters; the practice becomes weekly and ongoing
- •Writing forces active observation of what you value in someone
- •Shifts focus away from trivial annoyances toward gratitude
- •Creates “stored goodwill” that adds resilience during conflict
- •Appreciation becomes a database of values, not a one-time gesture
Employee-First Leadership at Scale: Ed Bastian’s “Virtuous Cycle” at Delta
Don highlights Delta CEO Ed Bastian as a modern leader who prioritizes employees so they can prioritize customers. The model links care, training, and resources to customer experience and premium performance, reinforcing the cycle with profit sharing.
- •Philosophy: employees first so customers don’t have to fight for care
- •Virtuous cycle: invest in employees → better service → stronger revenue → reinvest
- •Profit sharing: ~10% of profits returned to employees
- •Symbolism matters: profit sharing delivered on Valentine’s Day like a “love letter”
- •Maintaining trust at 120,000-person scale is hard but intentional
Leading Through Crisis: Over-Communicating When You Don’t Have All the Answers
During COVID, Bastian’s approach was frequent livestream updates, transparency about unknowns, and open Q&A. The takeaway: in uncertainty, leaders must be present and communicative rather than retreating behind busyness.
- •Crisis leadership requires more communication, not less
- •Daily livestreams to employees: what’s known and what isn’t
- •Transparency builds credibility and reduces rumor-driven fear
- •Taking questions creates psychological safety and trust
- •Leadership is visibility and steadiness under pressure
Learning from History and Parenting: Teddy Roosevelt, Absence, and Family “Contracts”
Don shares research on Teddy Roosevelt and Teddy Roosevelt Jr., focusing on the hidden costs of greatness at home. The discussion turns to modern work-life tradeoffs and the value of explicit agreements that protect family priorities.
- •TR Jr. struggled under the pressure of an extraordinary father’s legacy
- •Teddy Roosevelt Sr. wasn’t “bad,” but was often absent and missed the stress
- •Don’s family agreement: no more than three nights away per week
- •Rationalizations (“I do it for the family”) often mask ego and misaligned values
- •Make expectations explicit during calm periods, not only during conflict
What Mentorship Really Is (and Isn’t): Evolving Relationships, Not Street-Asked Transactions
Simon and Don define mentorship as a mutual, evolving relationship where someone consistently makes time for you. They distinguish mentors from champions and warn against confusing paid programs or influencer “gurus” with true mentorship.
- •A mentor makes time for you—like a friend with deeper care
- •Mentorship evolves; you can’t demand it from a stranger
- •Mentor-mentor dynamic: both learn, regardless of age or status
- •Mentors vs champions: champions can advance your career; mentors focus on you
- •Beware transactional “mentorship” sold online as a product
Why Wooden-Style Leadership Is Rare: Short-Term Pressure, Skill-Building, and Bench Strength
They confront the central frustration: everyone admires people-first leadership, yet few leaders practice it. The reasons include short-term incentives, fear of mistakes while developing people, and a lack of patience to build capability across the team.
- •Short-termism discourages investment in development and culture
- •Leaders revert to “the best person” to avoid mistakes, weakening the bench
- •David Marquet submarine story: train more people, even through early failure
- •Infinite mindset helps teams stay calm and effective during setbacks
- •Culture collapses when leaders panic, blame, or humiliate to hit numbers
Storytelling Advice to Apply Today: Know Your Audience and Make It a “You Story”
Don closes with a tactical storytelling principle: most people fail because they don’t understand who they’re speaking to. Great stories are tailored for the listener’s context and needs, not the speaker’s ego.
- •The biggest storytelling mistake: not knowing the audience
- •Do the work: research who you’re trying to influence
- •Small tweaks in framing can dramatically increase impact
- •Avoid “me stories”; craft stories that serve the listener
- •Storytelling is leadership: impact depends on empathy and intent
