Two-Pizza Teams and Psychological Safety

Some organizations have no heart at all. The best have three!

That’s the thesis of the new book, The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation, co-authored by our guests, Phil Le Brun and Jana Werner. Both work with leaders operating at global scale—Phil as an Executive in Residence at Amazon Web Services, and Jana as a Global Executive Advisor at AWS—helping organizations navigate complexity, change, and continuous transformation.

In their book, Phil and Jana introduce a clear contrast between what they call Tin Man organizations and Octopus organizations. Tin Man organizations are rigid, highly centralized, and overly dependent on a small group of decision-makers at the top. Like the character in The Wizard of Oz, they operate with structure but no heart. Decision-making slows, intelligence gets trapped in the hierarchy, and employees often wait for direction rather than contributing meaningfully.

Octopus organizations, by contrast, are alive with three hearts. They are intelligent, adaptive, and responsive. A strong central purpose keeps everyone aligned, but authority and decision-making are distributed to the people closest to the work. Teams are empowered to sense, decide, and act, allowing the organization to learn, adapt, and thrive in real time.

A central contribution of the book is the identification of what Phil and Jana call organizational “anti-patterns”—recurring leadership behaviors and systems that feel reasonable in the moment but consistently undermine clarity, trust, cohesion, and performance. These patterns exist even in organizations with talented people and strong intentions.

In this episode, we explore several anti-patterns in depth: the lack of clarity that leaves people guessing what truly matters; the overuse of corporate jargon that creates distance and mistrust; purpose statements that are words on a page rather than guides for behavior; and cultures that elevate individual stars at the expense of cohesive, high-performing teams. We also discuss why fast, open information flow is essential for adaptability and well-being.

Phil and Jana also reconfirm our own understanding that well-being cannot be created through perks or programs—it emerges from how people are treated, trusted, and empowered, and how work is designed and decisions flow. For leaders who care about performance, well-being, and building more humane organizations, this episode offers practical insight into creating workplaces that truly thrive.

The post Phil Le-Brun & Jana Werner: How Organizations Thrive When They Have Three Hearts appeared first on Mark C. Crowley.