Simon Sinek commands attention when he speaks, blending intelligence with charisma. His distinctive spiky hair, thick-rimmed glasses, and subtle British inflection evoke a modern thinker. But it's his precise word choice and thoughtful delivery—backed by scientific research—that truly captivate, delivered with the poise of a seasoned performer.
Last winter, his video on millennials exploded online, amassing tens of millions of views on Facebook and YouTube. Shared across generations, it held viewers spellbound for 15 minutes amid constant distractions, thanks to Sinek's masterful mix of humor, empathy, and truth.
Related: Simon Sinek on the Millennium Question
At 43, Sinek is among the most in-demand leadership experts. His 2009 TED Talk ranks third all-time in popularity. Author of three bestsellers—with another forthcoming—he's advised the military, global corporations, and members of Congress. Recently, he's focused on the "millennial question."
In the viral clip, he lists common critiques of those born post-early 1980s: entitled, narcissistic, selfish, unfocused, lazy. Addressing a mixed audience, he attributes these to "failed parenting strategies"—participation trophies and constant affirmations of being "special." This, he argues, leaves many unprepared for workplace realities, driving escapism via social media akin to addiction.
The explanation resonates deeply. Now, in a luxury Dallas hotel suite overlooking downtown—here to address thousands of American Airlines managers—Sinek reflects on those points with me.
ROBERT ASCROFT; BACKGROUND: STOCK PHOTO PESHKOV/123RF
I share my early-80s birth year, participation trophies (distinct from earned ones), and note millennials vary widely—a classic millennial defense, I admit.
"There are things that happen in the formative years of our lives that affect the way we see the world."
Sinek chuckles at the irony. "Of course people are all different," he says. "But generational patterns emerge from shared experiences. Great Depression survivors rationed, becoming frugal. Baby Boomers, amid Vietnam and Nixon, grew cynical of authority. Technology revolutionized millennials' world with unprecedented access—shaping behaviors, if not universally."
Soon, I'm rethinking my generation, relationships, and life choices. Sinek's persuasiveness is undeniable.
***
Before his appearance, staff fire T-shirt cannons into the crowd of American Airlines middle managers. Sinek emerges in a sharp gray jacket, designer jeans, skater shoes, and headset—no intro needed. He launches into a story from a 2014 TED Talk about 2009 Afghanistan.
In a valley ambush, Captain William Swenson, later Medal of Honor recipient, braved fire to save lives. Footage shows him kissing a dying soldier's forehead before returning to battle.
ROBERT ASCROFT
"I wondered: 'What creates such people?'" Sinek asks softly. "Why don't I work with folks like that?" The answer: environment fosters deep bonds.
"Military medals reward sacrifice for others. Business bonuses reward sacrificing others for gain," he notes, met with nods.
Trust echoes our tribal past, amid dangers like weather or predators. Sinek sketches a circle: danger outside, safe inside. "Nothing's changed."
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Brain chemicals persist: Endorphins mask pain; dopamine fuels achievement (but addictive); serotonin brings pride; oxytocin builds trust—enabling handshake deals.
In tribes, leaders ate first but protected all. Today, leaders gain perks but must charge into danger.
Related: 5 Things Strong Leaders Do
"When people believe this, they love you," Sinek says. Leaders must convey: "I've got your back. Nothing you break I can't help fix. I believe in you when you don't."
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The audience is rapt. My notes: fluid, dramatic delivery.
Before hundreds of American Airlines veterans, he adds: "That's why people love Southwest." Gasps ripple.
***
Born in England, Sinek's accent adapts. Parents urged passion pursuits. At Brandeis, a "Culture and Cognition" course sparked anthropology majoring in urban culture.
Mid-90s fieldwork with Massachusetts State Police explored public relations post-L.A. riots. He shadowed officers, even in vests during stops—troubled more by public hostility than expected.
Law school in London aimed at prosecution, but culture prioritized style over substance. Pivoted to advertising, excelling in persuasion. Built a marketing firm—three great years, one disastrous.
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His vision: "A world where most wake inspired to work, feel safe there, return fulfilled."
Exhaustion masked as success; poor sleep, isolation. Neuroscience readings revealed patterns mirroring his marketing insights. He discovered why people act—testing on himself by dissolving his firm, pondering Why.
We rally around shared values like tribes. Great leaders articulate Why: MLK for civil rights; Jobs for Apple.
Related: Why are you doing what you are doing?
From 1980s, firms "balanced books on humans' backs," per Jack Welch's GE model—exponential growth via relentless pressure, layoffs. Fortune's "Manager of the Century" (1999), but toxic culture replicated widely. Sinek counters this, promoting value-aligned hires, battlefield-like care.
ROBERT ASCROFT, TAKEN AT AL MAR IN BROOKLYN, NEW YORK
Friends urged corporate talks; U.S. Air Force early adopter. Now leads a 20-person team. Seeing concepts spread fulfills him.
***
His Impact Theory with Tom Bilyeu went viral post-New Year's 2016—millennials tangent exploded.
Questions arise everywhere; he researched deeply.
Related: 6 Habits of Successful Millennials
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Bilyeu: "Shocked by virality, but it fit—succinct issue diagnosis plus solutions: real relationships over screens." Amid tech shifts, parenting/employer changes explained macro trends powerfully.
Sinek's theories converge: Treat youth as humans needing dignity. Business must teach patience, fulfillment.
I question some generalizations—entitlement not millennial-exclusive; irony of social media spread. Yet his vignettes mesmerize; empathy is hard to refute. More needed.
"When Sinek speaks, it's impossible to dispute everything. It's part of his genius."
Disarmingly witty, scholarly confident—world benefits.
ROBERT ASCROFT
Back onstage, Sinek praises Southwest: Leaders trust rule-breakers for customers—upgrades, early boards, free drinks. Empowerment avoids PR disasters.
He does fewer speeches, prioritizing home, relationships. Rejects 39/40 invites; free for military, premium for firms. Only genuine culture-changers.
"We've got dysfunction; new leadership committed long-haul. Help?" Absolutely!
Thus, weeks with American Airlines. He mocks senior-only toilet cleaning as privilege.
Notes, nods abound. "Be the leader you wished for." Q&A:
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Leadership metrics: asymmetrical—like sick days, depression scripts. Personality irrelevant; authenticity key.
Woman: "Best from people?" Wrong question. "Empathy: 'What can I do to help?'"
"One of the most important feelings a leader can express is, 'I've got your back.'"
Pauses. True test:
"When you ask 'How are you?'—do you care?
Related: Why a Compassionate Leader Gets Results
This article originally appeared in the August 2017 issue of SUCCESS magazine.
