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