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 cover

• Why the “organization as a machine” model is breaking down
• The Octopus Organization metaphor and distributed intelligence in action
• How clarity and context enable decentralized decision-making
• Ownership vs permission and the pigs-and-chickens lesson
• Why real innovation must be embedded across every layer of the organization
• How curiosity and intelligent failure drive continuous transformation

Episode Timeline

00:00 Highlight and introduction to the Octopus Organization

02:00 Guest introductions and background

04:30 If you really know me… personal stories from Jana and Phil

07:40 Defining strategy as choice and what not to do

10:00 Tin Man vs Octopus organizations

13:30 How decentralization increases alignment

16:00 Ownership, permission, and single-threaded leadership

20:00 Amazon leadership principles and disagree-and-commit

22:30 Creating organizational clarity at scale

26:00 Focus, subtraction, and the mountaineering story

28:30 Durable needs and strategy at Amazon

30:30 Complicated vs complex systems in transformation

33:00 Curiosity, experimentation, and intelligent failure

36:00 The monkey-on-a-pedestal lesson

38:00 Centralized vs decentralized innovation

41:00 Lighting a thousand fires and continuous transformation

44:00 Why this model outperforms traditional change programs

45:30 Where to learn more and connect with the authors

Additional Resources

Book: The Octopus Organization

Website: https://www.theoctopusorganization.com

Jana Werner LinkedIn: https://www.linkedin.com/in/janawerner1/

Phil LeBrun LinkedIn: https://www.linkedin.com/in/phillebrun/

Watch now on Youtube: https://youtu.be/qcD2GmX5uUI

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 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 function

Episode Timeline:
00:00 Introduction to Outthinkers Podcast

01:23 Meet Mark Thompson: CEO Coach and Author

02:06 The Seven Stakeholders of CEO Success

02:42 Mark's Unique Coaching Methods

04:10 Personal Insights and Strategy Definition

06:30 The Reality of Becoming a CEO

08:58 Navigating Board Dynamics

20:57 Interacting with the Board: Key Strategies for Aspiring CEOs

21:28 Listening and Broadening Your Perspective

22:44 Understanding the Role of Strategy Officers

26:36 Navigating Peer Dynamics and Leadership Transition

33:03 Building Relationships with the CEO

35:44 Engaging with Investors and Owners

39:56 The Importance of Customer Influence

44:17 Final Thoughts and Resources for Aspiring CEOs

Additional Resources:
•Mark Thompson: Chief Executive Alliance — https://chieexecutivealliance.com

Watch now on Youtube: https://youtu.be/wuh4Rn7erxU

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

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 wins

Episode Timeline

00:00 Introduction to Outthinkers Podcast
00:35 Bill George on Medtronic's Impact
01:40 Bill George's Leadership Journey
05:00 Defining Strategy and Purpose
10:32 Authentic Leadership Explained
12:45 Challenges and Examples of Leadership
16:04 Personal Growth and Leadership
20:53 Developing Self-Awareness as a Leader
22:15 Facing Crucibles: Overcoming Tough Times
23:47 Exercises for Self-Discovery
25:33 The Power of Small Groups
27:32 Long-Standing Support Systems
29:28 Assessing Leadership Values
33:01 Effective Metrics for Leadership
39:56 Engaging with Bill George

Additional 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.com

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

Meet Jon Levy — behavioral scientist and author of Team Intelligence: How Brilliant Leaders Unlock Collective Genius and the NYT/WSJ bestseller You’re Invited. Jon has spent years studying human behavior and leadership mechanics, advising companies on how to build teams that actually perform—beyond leadership myths and buzzwords.

We often hire “A-players,” roll out values, and assume great leadership traits will carry us. Then reality hits: strategy doesn’t execute itself—teams do. Jon explains why the smallest unit of performance is the team, why stacking stars backfires, and how culture and language shape what people actually do. If you’re trying to align leaders who don’t buy the data, this one’s for you.

You’ll learn how to engineer collective intelligence—the practical habits, roles, and rituals that raise a team’s game, how to recruit and empower “glue players,” and how to make strategy felt when spreadsheets won’t persuade.

• Culture as operating system: the sayings, status cues, and rituals that drive behavior (Apple’s “surprise and delight,” LEGO’s “fireside”).
• Bursty communication: why teams should “work together, then work apart” to boost problem-solving.
• Glue players: high-EQ, team-first multipliers (and why too many stars tank performance).
• Make the implicit explicit: roles, skills, and “player cards” that speed decisions.
• Trust, not traits: honesty, competence, benevolence—and dealing with the dark tetrad at work.
• When data won’t convince: crafting a narrative that makes people feel the better future.

00:00 Introduction

00:36 Coming Up...

01:47 Unpacking Team Intelligence with John Levy

02:47 Insights on Leadership and Team Dynamics

05:13 The Role of Culture in Organizations

13:49 The Impact of Language on Behavior

16:54 The Concept of Glue Players

18:14 The Key to Predicting Success in Basketball

19:02 Characteristics of Glue Players

21:25 The Importance of Team Dynamics

23:49 The Antwerp Diamond Heist: A Lesson in Teamwork

27:52 Making Implicit Knowledge Explicit

29:36 The Dark Side of Team Dynamics

31:29 Understanding Trust in Teams

34:06 The Role of Emotion in Strategy

35:02 Conclusion and Final Thoughts

• Jon Levy — Website: https://www.jonlevy.com
• Book: https://www.jonlevy.com/team-intelligence
• LinkedIn: https://www.linkedin.com/in/jonlevytlb

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

Christina Farr is an investor, startup advisor, and former health-tech journalist. She’s the author of The Storyteller’s Advantage: How Powerful Narratives Make Businesses Thrive and the creator of the Second Opinion newsletter, where she decodes healthcare and technology for leaders.

Most leaders try to move markets with features, roadmaps, and metrics. But the winners often move them with narrative—stories that rally investors, customers, and teams to build the future with them. Christina unpacks how great storytellers create belief that becomes momentum.

You’ll learn a simple framework to make your strategy legible and compelling, how to pick the right plot for your message, and practical ways to craft origin stories, pitch decks, and CEO communications that persuade.

In this episode we cover:

• The SOAP framework: Surprise, Openness, Authenticity, Pathos
• Seven classic plots for business (from David vs. Goliath to Rebirth) and when to use each
• Case studies: PillPack vs. incumbents; Apple’s comeback; Microsoft’s reinvention; WeWork’s cautionary tale
• Fundraising and sales: decks that move capital and customers
• Leading in tense moments: speaking to charged issues without fracturing culture

Episode Timeline:

00:00 – Highlight from today’s episode

01:05 – Introducing Christina + the power of narrative in business

03:05 – “If you really know me…”

04:20 – What is strategy? Story as prognostication

07:10 – Why story beats data alone in pitches, sales, and retention

10:55 – The SOAP framework (Surprise, Openness, Authenticity, Pathos)

18:40 – Engineering surprise; calibrating vulnerability

22:00 – Seven plots leaders can borrow (with modern brand examples)

28:45 – Case study: PillPack’s David vs. Goliath playbook

32:40 – Rebirths and tragedies: Apple, Microsoft, WeWork

36:10 – Origin stories that travel (and ones that don’t)

38:10 – CEO comms on divisive topics, without breaking culture

39:20 – Where to learn more from Christina

Additional Resources:

• Book: The Storyteller’s Advantage — Christina Farr (Basic Venture) -https://basic-venture.com/titles/christina-farr/the-storytellers-advantage/9781541704299/
• Newsletter: Second Opinion - https://secondopinion.media/
• Christina Farr on LinkedIn - https://www.linkedin.com/in/christinafarr/

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

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 AI
• Why this moment rivals—and perhaps surpasses—the dot-com boom in its impact
• How AI is both lowering the floor of creativity, making it easier for anyone to create, and raising the ceiling, expanding what’s possible for professionals
• How personalization at scale is transforming customer experiences
• And what this means for the future of brands, creativity, and human originality

It’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 performance
• The Oxford evidence: how self-reported wellbeing maps directly to productivity in real work
• Belonging > boss quality as a driver of retention—and how leaders actually build it
• Caring vs. being nice: creating psychological and emotional safety without lowering the bar
• A practical definition of strategy: know where you’re going, plan with rigor, pivot fast when reality disagrees

Episode Timeline:

00:00 – Introduction

01:10 – Guest introduction and the case for feelings over dashboards

03:05 – “If you really know me…” and how Mark learned to lead from the heart

06:45 – Managing differently: proof from 25 years of top-performing teams

09:30 – Mark’s definition of strategy: plan hard, pivot faster

12:20 – Why wellbeing (not satisfaction) sets the stage for peak performance

15:10 – What wellbeing actually is—and why managers determine most of it

18:05 – Up to 95% of behavior is emotion-driven: implications for leaders

20:30 – Engagement stalled; the Oxford call-center study on wellbeing → productivity

25:40 – Caring vs. nice; HeartMath and the science of coherence

31:00 – Selecting and developing leaders who elevate others (not just individual stars)

36:10 – Belonging as the #1 driver of retention—and how to create it

39:20 – Where to start: know yourself, clarify values, design team-first systems

42:15 – Reward the team first (then individuals) to eliminate zero-sum competition

44:10 – How to keep learning from Mark + close

Additional Resources:

• Website: https://markccrowley.com
• LinkedIn: https://www.linkedin.com/in/markccrowley
• Books: Lead From the Heart; The Power of Employee Wellbeing
• Podcast: Lead From the Heart

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

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 strategy
• Where the next choke points may emerge: AI compute, batteries/EVs, and the energy transition
• The 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 failure

Episode Timeline:

00:00 – Cold open: rare earths and leverage

02:00 – Guest introduction and Eddie’s background

05:45 - Strategy as “winning tomorrow,” not just today

07:02 - Defining choke points (dominance + substitution)

11:20 - The “impossible trinity” explained with historical arcs

27:05 - Should firms adapt or shape policy?

30:05 - Emerging choke points: AI chips, batteries, EVs

38:05 - U.S. industrial policy (MP Materials, Intel) and what comes next

Additional Resources:

Book: https://www.penguinrandomhouse.com/books/726149/chokepoints-by-edward-fishman/

X (Twitter): https://x.com/edwardfishman?lang=en

LinkedIn: https://www.linkedin.com/in/edward-fishman

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