Leader to Leader | Becoming an Octopus Organization: A New Model for Leadership in the AI Age

Feb 8, 2026

Co-authored with Steve Wunker and originally published in the journal Leader to Leader.

Abstract

Steve Wunker (Managing Director of New Markets Advisors) and Jonathan Brill (Futurist-in-Residence at Amazon) discuss their concept of the “Octopus Organization.” They write that “as artificial intelligence moves from novelty to necessity, organizations face a sobering truth: traditional structures can’t keep up.” They believe that the Octopus Organization represents a fresh approach and “a new archetype for leadership.” Their “framework is based on our work as pioneers and doers as well as in-depth discussions with more than fifty leaders in AI, academia, and industry.” Examples are cited from companies such as HelloFresh, Stripe, and Microsoft. They identify a major shift in the role of middle managers, which “becomes less about directing and more about enabling – asking the right questions of AI systems, guiding teams in judgment, and surfacing risks that machines might miss.” In the Figure “the Neural Necklace: How Information Powers the Whole,” they identify four actions; in their words: Put Boundaries around AI; Redefine “Manager”; Map Decision Lanes, and Hunt Blockers. To transition into this new type of organization, they offer questions leaders should ask, such as “What might an AI-enabled process save in terms of time and labor versus your old ways of doing things?”

Click here to access the full article on Leader to Leader

Leader to Leader cover page

Interested in learning more about the Octopus Organization?

Leverage

What Matters Next.™

Sign up for the What Matters Next newsletter, your deep injection of intelligence on why the world is changing, what to do about it and how to take action.