The Learning Leader Show With Ryan Hawk Podcast By Ryan Hawk cover art

The Learning Leader Show With Ryan Hawk

The Learning Leader Show With Ryan Hawk

By: Ryan Hawk
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As Kobe Bryant once said, “There is power in understanding the journey of others to help create your own.” That’s why the Learning Leader Show exists—to understand the journeys of other leaders so that we can better understand our own. This show is full of learnings taught by world-class leaders—personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgrounds—CEOs of multi-billion dollar companies, best-selling authors, Navy SEALs, and professional athletes. My role in this endeavor is to talk to the most thoughtful, accomplished, and intentional leaders in the world so that we can learn from them as we each create our own journeys.Learning Leader LLC 062554 Career Success Economics Management Management & Leadership
Episodes
  • 653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders

    653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders
    Sep 14 2025
    Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub. Notes: Key Learnings Strategic CEO Job Search Criteria – Sukhinder had four non-negotiables: macro tailwinds/good market, customer she could be passionate about, strong business model, and a role where she could "learn for miles" for 5-8 years. Only two companies met her criteria in 18 months of searching."Sell, Interview, Sell" Hiring Process – First meeting is 50% selling the opportunity to attract top talent. Only after candidates lean in do you shift to intensive interviewing with leadership team exposure.The Virtuous Cycle Framework – Customer at the top, supported by "high purpose, high performance, high people" culture. "It's an 'and,' not an 'or'" - you don't get to choose just one element.Back-Channeling is Critical – Reference checking happens throughout the entire interview process, not just at the end. "The most important thing is not just front channel... it's all the back channel."Values Alignment Over Pure Qualifications – "Go where my values fit and my strengths are valued." Cultural fit becomes the deciding factor in close hiring calls, not competence.The Layoff Leadership Test – Six weeks after joining, Sukhinder laid off 900 people based on McKinsey benchmarking. Showed consistency between the outside-in analysis presented to the board and transparent communication to employees.Portfolio of Bets Strategy – Balance growth, profitability, and customer happiness through diversified initiatives ranging from "safe moves" to "flyers," with clear probability assessments.Consistency as Culture Foundation – "Culture means consistency of message and what's important." Authenticity through change, not resistance to change.The 10-Slide CEO Interview Deck Framework: Vision statement (destination in 2-3 years)Outside-in market analysisCompetitive landscapeSWOT analysis of current positionFive key strategic movesImplementation approach ("the how")Estimated outcomes with probability ranges Practical Application: Job Search Strategy – Define 4-5 non-negotiable criteria upfront. Be willing to wait for roles that truly meet your standards rather than taking "the job before the job."Interview Preparation – Always build a comprehensive thesis deck even if not requested. Use it to clarify your own thinking and demonstrate strategic capability.Hiring Excellence – Spend equal time selling the opportunity and evaluating candidates. Use diverse interview panels and back-channel extensively throughout the process.Cultural Leadership – Be consistent in messaging across all stakeholders (board, investors, employees). Authenticity enables trust during periods of change.Strategic Planning – Frame initiatives as a portfolio of bets with clear probability assessments. Balance growth, profitability, and customer satisfaction rather than optimizing for one. Leadership Hiring Process: The CEO interviews top 2-3 levels even without hiring authorityDiverse interviewer panels with "bar raisers"Business problem-solving presentations in the final roundsMultiple leadership team interactions before the final decision Life Lessons: Patience in Career Progression – Sometimes the right opportunity requires waiting. Sukhinder was frustrated during 18 months of searching but found the perfect fit.Preparation Separates Candidates – The depth of strategic thinking demonstrated in final presentations often determines CEO selections.Culture Survives Through Consistency – Not avoiding change, but maintaining consistent values and communication approach through inevitable changes.Leadership Requires Tough Decisions – Laying off 900 people six weeks into the role, but doing it transparently and based on clear data/analysis.Value Creation Through Alignment – Finding roles where your strengths are valued and values align creates exponentially better outcomes than pure skill matching.Systems Thinking Builds Trust – Sharing appropriate "behind the scenes" context helps teams understand difficult decisions and builds long-term credibility.Early Career Focus – "Do great work for great people." Find talented leaders to apprentice under and work exceptionally hard to maximize learning.Authenticity Enables Performance – Being genuine about challenges and changes builds stronger relationships than trying to maintain artificial stability.Strategic Communication – Frame personal asks in terms of organizational benefits. Make it about solving their problems, not ...
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    58 mins
  • 652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy

    652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy
    Sep 7 2025
    Apply to be in my next Learning Leader Circle - https://learningleader.com/leadership-circles/ This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Notes: Key Learnings The Mad Scientist Emotional Profile – High achievers typically have both high positive and high negative affect. "Hustlers, hard workers, strivers, entrepreneurs, ambitious people, they're in that quadrant of high positive, high negative affect." This creates intensity but requires management of negative emotions.Dangerous Negative Affect Management – People try to manage high negative affect through alcohol, excessive internet use/pornography, and workaholism. "The isms, the addictions, they're almost all negative affect management techniques."Two Best Ways to Manage Negative Affect: Faith, Spirituality, Philosophy - "Every day, go deep" into transcendent practicesPhysical Exercise - "Go pick up heavy things" - resistance training moderates negative emotions Arthur's 4:30 AM Protocol – Wakes at 4:30, works out 4:45-5:45, attends mass 6:30-7:00, then has high-protein breakfast with dark coffee at 7:45 for 4 hours of peak creative focus. "I get four hours of creative concentration with maximum dopamine."Exercise Reduces Unhappiness, Doesn't Create Happiness – "Working out hard... moderates negative affect. It makes you less unhappy" rather than directly increasing positive emotions.The Failure Journal Method – Write down failures/disappointments, return after 3 weeks to note learnings, return after 2 more months to identify good things that resulted. This installs learning in the prefrontal cortex rather than letting it "float around limbically."Early Success Can Be Dangerous – Scholars rejected for early research grants outperformed those with early success. "Much better is when you do the work and build yourself up... be a wholesaler before you become a retailer."Management Doesn't Provide Flow – "There's one kind of job where you don't get flow, and that's management... you're getting jerked from thing to thing to thing." Being CEO was "satisfying, but not enjoyable."Intelligence Must Serve Others – "Intelligence is just another gift... whether or not it makes you happier depends on whether or not you're using it to make other people happier." Denigrating others for lower intelligence indicates misusing your gift.The Arrival Fallacy – Olympic gold medalists often experience depression after winning because positive emotion comes from progress toward goals, not achieving them. "Your positive emotion doesn't exist to give you a permanent good day."Two Midlife Crisis Solutions: Focus on what age gives you rather than takes awayChoose subtraction over addition - appreciate what you no longer have to do Making Changes Stick Requires Three Elements: Understand the science - Know why something worksChange your habits - Actually implement different behaviorsTeach it - Explain it to others to cement learning in the prefrontal cortex The Happiness Formula – "Use things, love people, worship the divine" instead of the natural impulses to "love things, use people, and worship yourself." Multi-generational Living Benefits – Arthur lives with adult children and grandchildren: "The research is clear that the closer you are to your grandchildren... the better it is for everybody." Quotes: "I get four hours of creative concentration with maximum dopamine in my prefrontal cortex... ordinarily I would get an hour and a half, two hours of real clarity.""The isms, the addictions, they're almost all negative affect management techniques.""Working out hard... makes you less unhappy. The research is very clear.""Being the boss isn't that fun. It just isn't.""I have carefully accounted for all of my days of happiness. They add up to 14." (Emir of Cordoba)"What's first prize in a pie eating contest? The answer is pie. So I hope you like pie.""Beware the corner office boys. Beware the corner office.""Use things, love people, worship the divine.""Watch one, do one, teach one." (Harvard Medical School)"Don't trust your impulses. Your impulses are to love things, use people, and worship yourself." Life Lessons Develop Daily Discipline Early - A Consistent morning routine with exercise and spiritual practice creates optimal brain chemistry for peak performance throughout the day.Manage High Achievement Personality - If you're a driven person, recognize you likely have high negative affect that needs healthy management through exercise and transcendent practices.Reframe Career Setbacks - Early failures often build stronger foundations than early successes. Use disappointments as learning opportunities through systematic reflection.Question Management Ambitions - Consider whether you enjoy management or just want...
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    57 mins
  • 651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)

    651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)
    Aug 31 2025
    Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Shaka Sengor spent 19 years in prison for killing a man. He’s transformed his life through not making excuses and taking full ownership of his decisions. Now, he’s a New York Times best-selling author who has been called a “soul igniter” by Oprah. His latest book is called How to Be Free. Notes: The Permanence of Split-Second Decisions – At 17, shot three times on a Detroit corner. At 19, he killed a man in a conflict after creating a narrative that he would "shoot first." Sentenced to 17-40 years for second-degree murder. "I try to teach young people about understanding the permanence of a 30-second decision."Books as Portals to Freedom – Read over 1,500 books during 19-year incarceration, starting with street literature (Pimp, Black Gangster) as a gateway to philosophy (Plato, Marcus Aurelius). "Books allowed me to escape in the most literal sense... a portal into other worlds."Prison Mentors Changed Everything – Lifers became his guides: "These are men serving life sentences who came equipped with wisdom about what's on the other side... they guided me to books that shattered old narratives and opened possibilities."Reading Creates Writing Excellence – Speed-reading skill from age 8 (learned during punishments with encyclopedias) combined with voracious prison reading, led to becoming a NY Times bestselling author. "You have to be a practitioner of the craft every day."Journaling as Transformation Tool – "It was the most healing experience I've ever had to speak to my truth, speak to the pain points." Uses 20 different journals, writes everywhere - planes, shower thoughts on phone, margins of books.Hidden Prisons We All Carry – "The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us, built from grief, anger, shame, trauma." Everyone has internal prisons that can be opened.Vulnerability as Strength, Not Manipulation – Authentic vulnerability vs. weaponized oversharing. "Human beings have this innate ability to suss out the truth. Authenticity and vulnerability is the super unlock... being true to your center."Community Through Shared Truth – Prison taught extreme friendship criteria: "Are they willing to serve a life sentence for you or die for you?" Now applies accountability standards: showing up consistently, being loyal to family first.Violence Born from Fear – "Reactionary violence is typically born out of fear, being afraid." Prison taught him to see "the child in people" who are acting out, leading to empathy instead of escalation.Voluntary Hardship Builds Resilience – Monthly 3-day fasts in solitary confinement prepared him for food deprivation punishment. "None of us get through life without suffering... that extra hour a week can change your life's outcomes."Composure Through Self-Awareness – Developed through journaling about times he wasn't composed. "Once you've written it down, you own it. When you own it, you can control it. When you can control it, it's easy to become composed."Remove All Excuses – Florence Nightingale quote: "I never gave or took any excuse." Despite a felony record, a violent crime conviction, and 20 years in prison, he chose to "lead a great life" by removing every excuse.The Ben Horowitz Friendship – Unlikely brotherhood with VC billionaire, starting from Oprah's introduction, bonding over music and culture until 3 AM conversations. Shows authentic relationships transcend backgrounds. Quotes: "I try to teach young people about understanding the permanence of a 30-second decision.""I was in prison before I stepped foot in a cell, and I was free before they ever let me out.""The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us.""Books allowed me to escape... a portal into other worlds.""Once you've written it down, you own it. When you own it, you can control it.""I never gave or took any excuse." (Florence Nightingale)"Master your thinking, master your destiny.""Violence is typically born out of fear, being afraid.""If you can see the child in the person that's acting out... it equips you to have more empathy.""None of us gets through life without suffering. At some point, we're all gonna go through adversity.""I chose to lead a great life... I removed every excuse." Life Lessons: Face Your Internal Prisons – Identify the shame, anger, grief, and trauma that create mental prisons. Recognize that these have doors that can be opened through conscious workUse Reading as Escape and Growth – Books provide mental freedom regardless of physical circumstances. Start with what interests you, then expand ...
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    52 mins
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This is the best podcast. Regardless of who you are or where you’re at in life, you’ll absolutely find incredible value. Literally every episode shared ways to just be a better person overall. And Ryan asks meaningful, impactful questions that drive to tactical approaches that we can actually use. Very grateful for him and this show.

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