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OutthinkersAuthor: Outthinker
The Outthinkers podcast is a growth strategy podcast hosted by Kaihan Krippendorff. Each week, Kaihan talks with forward-looking strategists and innovators that are challenging the status quo, leading the future of business, and shaping our world.Chief strategy officers and executives can learn more and join the Outthinker community at https://outthinkernetwork.com/. Language: en-us Genres: Business, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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#158 — Jana Werner & Phil Le-Brun: How to Build an Organization That Learns and Adapts Fast
Tuesday, 20 January, 2026
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
