Outthinkers

Jana Werner is a global executive advisor and Executive in Residence at Amazon Web Services, where she works with Fortune 500 leadership teams on organizational transformation and enterprise strategy. She holds a PhD in uncertainty dynamics in projects and has contributed to academic research and teaching at institutions including Oxford and the London School of Economics.Phil Le-Brun spent 31 years at McDonald’s, serving as International CIO and leading technology delivery across more than 120 countries. He is now an Executive in Residence at AWS, serving as an enterprise strategist and evangelist, with advanced degrees in systems thinking.Together, they are the authors of The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation.Most large companies still operate like machines. Rigid hierarchies, tight controls, and permission-based decision making may deliver predictability, but they quietly kill ownership, learning, and innovation.By contrast, the most adaptive organizations operate more like living systems, distributing intelligence, empowering teams, and enabling continuous transformation. Companies like Amazon demonstrate how decentralization, clarity, and ownership can create alignment rather than chaos.This episode explores how leaders can replace command-and-control structures with environments where innovation becomes everyone’s job.In this episode we coverWhy the “organization as a machine” model is breaking downThe Octopus Organization metaphor and distributed intelligence in actionHow clarity and context enable decentralized decision-makingOwnership vs permission and the pigs-and-chickens lessonWhy real innovation must be embedded across every layer of the organizationHow curiosity and intelligent failure drive continuous transformationEpisode Timeline00:00 Highlight and introduction to the Octopus Organization02:00 Guest introductions and background04:30 If you really know me… personal stories from Jana and Phil07:40 Defining strategy as choice and what not to do10:00 Tin Man vs Octopus organizations13:30 How decentralization increases alignment16:00 Ownership, permission, and single-threaded leadership20:00 Amazon leadership principles and disagree-and-commit22:30 Creating organizational clarity at scale26:00 Focus, subtraction, and the mountaineering story28:30 Durable needs and strategy at Amazon30:30 Complicated vs complex systems in transformation33:00 Curiosity, experimentation, and intelligent failure36:00 The monkey-on-a-pedestal lesson38:00 Centralized vs decentralized innovation41:00 Lighting a thousand fires and continuous transformation44:00 Why this model outperforms traditional change programs45:30 Where to learn more and connect with the authorsAdditional ResourcesBook: The Octopus OrganizationWebsite: https://www.theoctopusorganization.comJana Werner LinkedIn: https://www.linkedin.com/in/janawerner1/Phil LeBrun LinkedIn: https://www.linkedin.com/in/phillebrun/Watch now on Youtube: https://youtu.be/qcD2GmX5uUIThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

Mark Thompson is a CEO coach and author of CEO Ready. Born and raised in Silicon Valley and now working across emerging tech hubs, Mark prepares leaders for the leap from elite operator to enterprise chief. He’s worked with CEOs ranging from Richard Branson and Evan Sharp (co-founder of Pinterest) to Dr. Jim Yong Kim (former president of the World Bank) and Dave Chang (founder of Momofuku).Most executives assume the CEO seat is the natural “next step” for the highest performer. But Mark argues you earn readiness twice: first by delivering results, and then by winning belief outside your swim lane. In other words, performance gets you shortlisted—but it doesn’t get you selected.In this episode, Mark lays out the seven stakeholders who decide your fate as a CEO candidate (the board, investors/owners, peers, employees, customers, the current CEO, and you). We talk about what each group actually wants, how to build trust across the enterprise, and why the best CEO candidates develop “conversational fluency” across functions so they can lead beyond their lane.In this episode we cover:•Why “elite performance” only gets you halfway to CEO—and what earns belief the second time•The seven stakeholders who decide CEO readiness (and how to build a plan for each one)•How to show up to the board as more than a functional expert•Turning peers into partners (before the role forces the shift)•Building fluency across functions so you can lead the whole enterprise—not just your functionEpisode Timeline:00:00 Introduction to Outthinkers Podcast01:23 Meet Mark Thompson: CEO Coach and Author02:06 The Seven Stakeholders of CEO Success02:42 Mark's Unique Coaching Methods04:10 Personal Insights and Strategy Definition06:30 The Reality of Becoming a CEO08:58 Navigating Board Dynamics20:57 Interacting with the Board: Key Strategies for Aspiring CEOs21:28 Listening and Broadening Your Perspective22:44 Understanding the Role of Strategy Officers26:36 Navigating Peer Dynamics and Leadership Transition33:03 Building Relationships with the CEO35:44 Engaging with Investors and Owners39:56 The Importance of Customer Influence44:17 Final Thoughts and Resources for Aspiring CEOsAdditional Resources:•Mark Thompson: Chief Executive Alliance — https://chieexecutivealliance.comWatch now on Youtube: https://youtu.be/wuh4Rn7erxUThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

Bill George is one of the most influential leadership thinkers of our time. A former CEO of Medtronic and long-time Harvard Business School professor, he’s served on the boards of Goldman Sachs, ExxonMobil, Novartis, and the Mayo Clinic. His books including True North and True North: Emerging Leader Edition—have shaped how thousands of leaders approach purpose, values, and character.When performance pressure rises, it’s easy for leaders to drift from their values chasing quarterly metrics, external validation, and “style” over substance. Bill argues the opposite: sustainable performance springs from purpose, self-awareness, and a culture people believe in. We explore how to stay grounded as expectations, visibility, and success scale.You’ll learn how authentic leaders make the hard calls without becoming “nice at the expense of necessary,” choose metrics that drive meaning (not gaming), and build teams that keep you honest, learning, and aligned.In this episode we cover:•Authentic leadership: what it is and isn’t•Purpose-first strategy•The Medtronic metric: measuring outcomes people feel, not just inputs•Making tough people & portfolio decisions without losing your values•Building your leadership circle for honest feedback & growth•Short-term vs. long-term: preventing KPI gaming and hollow winsEpisode Timeline00:00 Introduction to Outthinkers Podcast00:35 Bill George on Medtronic's Impact01:40 Bill George's Leadership Journey05:00 Defining Strategy and Purpose10:32 Authentic Leadership Explained12:45 Challenges and Examples of Leadership16:04 Personal Growth and Leadership20:53 Developing Self-Awareness as a Leader22:15 Facing Crucibles: Overcoming Tough Times23:47 Exercises for Self-Discovery25:33 The Power of Small Groups27:32 Long-Standing Support Systems29:28 Assessing Leadership Values33:01 Effective Metrics for Leadership39:56 Engaging with Bill GeorgeAdditional Resources•Bill George — Website: https://www.billgeorge.org•LinkedIn: https://www.linkedin.com/in/williamwgeorge/•Book: True North: Emerging Leader Edition•Book: True North•Kaihan Krippendorff: https://www.outthinker.comThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

Join Jon Levy, a behavioral scientist and author, as he delves into the secrets of high-performing teams. He explains that the smallest unit of performance is the team, debunking the myth that star players guarantee success. Discover the concept of 'glue players'—team-first multipliers who enhance performance. Levy emphasizes the importance of culture as an operating system and the power of clear communication patterns. Trust, not just individual traits, drives team effectiveness, and he provides strategies for making implicit skills explicit.

Christina Farr, an investor and former health-tech journalist, discusses the power of storytelling in business. She reveals how narratives can outperform data in attracting investors and customers. Christina introduces her SOAP framework—Surprise, Openness, Authenticity, and Pathos—designed to craft compelling messages. The conversation dives into classic narrative plots like the 'David vs. Goliath' story and shares real-world examples from Apple and Tesla. She emphasizes effective origin stories and the impact of storytelling on company culture and strategy.

In this special in-person conversation recorded at Adobe’s global headquarters, host Kaihan Krippendorff sits down with Malte Bernholz, Vice President of Strategy and Incubation at Adobe.Malte brings a unique lens, combining years of experience in consulting and technology leadership, to unpack what might be the most significant technological shift of our lifetime. Together, Kaihan and Malte explore:The macro forces and creative trends redefining industries in the age of AIWhy this moment rivals—and perhaps surpasses—the dot-com boom in its impactHow AI is both lowering the floor of creativity, making it easier for anyone to create, and raising the ceiling, expanding what’s possible for professionalsHow personalization at scale is transforming customer experiencesAnd what this means for the future of brands, creativity, and human originalityIt’s a conversation about courage, imagination, and leadership at the edge of technological change.And for the first time, you can watch this conversation as well as listen—check out the video version on Outthinker.com or YouTube.Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

Mark Crowley is a longtime financial services leader who led consistently top-performing teams over a 25-year career. He’s the author of Lead From the Heart and the newly released The Power of Employee Well-being, a frequent contributor to Fast Company, and host of the Lead From the Heart podcast. In 2013, Mark was the first to publicize Gallup’s finding that only 30% of U.S. employees were engaged—helping ignite a decade-long debate about what truly drives performance.In this conversation, we explore why feelings and emotions—not dashboards—drive behavior, how the heart–brain connection shapes decisions at work, and why belonging outperforms “boss quality” as a predictor of retention. Mark connects lived leadership to research—from Oxford’s wellbeing–productivity link to HeartMath’s work on coherence—and shows how caring (not coddling) creates the conditions for sustained results.Whether you lead a business unit, a project team, or a transformation office, this episode will reframe how you raise performance by raising wellbeing—with specific, near-term moves any leader can make this week.In this episode we cover:Why traditional engagement efforts flatline—and why wellbeing is the more powerful lever for performanceThe Oxford evidence: how self-reported wellbeing maps directly to productivity in real workBelonging > boss quality as a driver of retention—and how leaders actually build itCaring vs. being nice: creating psychological and emotional safety without lowering the barA practical definition of strategy: know where you’re going, plan with rigor, pivot fast when reality disagreesEpisode Timeline:00:00 – Introduction01:10 – Guest introduction and the case for feelings over dashboards03:05 – “If you really know me…” and how Mark learned to lead from the heart06:45 – Managing differently: proof from 25 years of top-performing teams09:30 – Mark’s definition of strategy: plan hard, pivot faster12:20 – Why wellbeing (not satisfaction) sets the stage for peak performance15:10 – What wellbeing actually is—and why managers determine most of it18:05 – Up to 95% of behavior is emotion-driven: implications for leaders20:30 – Engagement stalled; the Oxford call-center study on wellbeing → productivity25:40 – Caring vs. nice; HeartMath and the science of coherence31:00 – Selecting and developing leaders who elevate others (not just individual stars)36:10 – Belonging as the #1 driver of retention—and how to create it39:20 – Where to start: know yourself, clarify values, design team-first systems42:15 – Reward the team first (then individuals) to eliminate zero-sum competition44:10 – How to keep learning from Mark + closeAdditional Resources:Website: https://markccrowley.comLinkedIn: https://www.linkedin.com/in/markccrowleyBooks: Lead From the Heart; The Power of Employee WellbeingPodcast: Lead From the HeartThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

Eddie Fishman is a senior research scholar at Columbia University’s Center on Global Energy Policy, adjunct professor of International & Public Affairs, and author of Choke Points: How the Global Economy Became a Weapon of War. A former U.S. State Department strategist, he served on the Secretary of State’s Policy Planning Staff and Foreign Affairs Policy Board, and led Russia/Europe sanctions policy—bringing a rare, in-the-room perspective to how economic power really works.In this conversation, we trace how “choke points”—where one nation dominates and substitutes are scarce—have turned minerals, microchips, and money flows into the quiet weapons of great-power rivalry. Eddie unpacks the geo-economic “impossible trinity”—why you can’t maximize interdependence, economic security, and geopolitical calm all at once—and what that trade-off means for leaders making bets on AI, batteries, and supply chains.Whether you’re steering strategy, procurement, or policy, this episode will change how you spot fragile dependencies, anticipate where pressure will build next, and engage policymakers before the rules harden around you.In this episode we cover:Why a true “choke point” = dominance plus low substitutability The geo-economic impossible trinity and its implications for business strategyWhere the next choke points may emerge: AI compute, batteries/EVs, and the energy transitionThe firm’s role: don’t just adapt to policy—shape it (how to engage upstream, practically)Industrial policy realities: U.S. moves on rare earths and semis—benefits, risks, and tolerance for failureEpisode Timeline:00:00 – Cold open: rare earths and leverage02:00 – Guest introduction and Eddie’s background05:45 - Strategy as “winning tomorrow,” not just today07:02 - Defining choke points (dominance + substitution)11:20 - The “impossible trinity” explained with historical arcs27:05 - Should firms adapt or shape policy?30:05 - Emerging choke points: AI chips, batteries, EVs38:05 - U.S. industrial policy (MP Materials, Intel) and what comes nextAdditional Resources:Book: https://www.penguinrandomhouse.com/books/726149/chokepoints-by-edward-fishman/X (Twitter): https://x.com/edwardfishman?lang=enLinkedIn: https://www.linkedin.com/in/edward-fishmanThank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.Follow us at outthinker.com/podcast

In this engaging discussion, Scott Anthony, a Senior Lecturer at Dartmouth’s Tuck School of Business and expert on disruptive innovation, delves into how disruption has shaped human history. He draws parallels between historical events like the invention of gunpowder and modern innovations, emphasizing lessons for today's leaders. Scott reveals how understanding patterns of disruption can empower organizations rather than instill fear. He outlines the roles essential for fostering innovation and shares insights that encourage proactive decision-making in a rapidly changing world.

Adam Brotman, former Chief Digital Officer of Starbucks and co-CEO of J.Crew, dives into the mindset needed for AI-first leadership. He shares insights from his conversations with tech visionary Bill Gates, emphasizing AI as a tool for enhancing decision quality rather than just productivity. Brotman discusses the challenging 'middle era' of AI and how leaders must adapt their strategies. He stresses that authentic inspiration, not technical know-how, is vital for CEOs to drive meaningful AI transformation across their organizations.