The Octopus Approach to AI

In this episode, Rich sits down with Stephen Wunker, innovation strategist, author, and Managing Director at New Markets Advisors. As the co-author of AI and the Octopus Organization, Steve brings decades of experience helping companies harness innovation to drive real strategic change.

Together, Rich and Steve explore how artificial intelligence is transforming the way organizations think, decide, and lead. They discuss the octopus as a metaphor for distributed intelligence—where agility at the edges connects seamlessly to alignment at the core—and share a practical framework for building the “superintelligent firm.”

From shifting the role of managers to freeing time for creativity and connection, this episode uncovers how leaders can use AI to reshape their organizations for the future.

If you’re looking to understand how strategy and AI truly intersect—and how to prepare your business for what’s next—this conversation is for you.

🔑 Key Quotes:

“AI has the ability to free up so much time that’s spent gathering and processing information. The real promise is giving people more time to coach, collaborate, and connect.”

“AI creates a fluidity of information—like a neural necklace in an octopus—enabling coordination but also potential dysfunction if left unmanaged.”

“AI brings intelligence and rapid action to the edge of the organization, empowering frontline teams while keeping decisions within smart guardrails.”

“In AI-infused workplaces, middle managers move from spending 25% of their time with people to 65%. That’s a massive unlock of capability.”

“Great ideas are easy if you start with great questions.”

⏱️ Timestamps:

(00:00) Deep Dive Interview with Stephen Wunker
(42:38) Practice Makes Profit
(45:18) League of Strategic Minds
(46:49) Winsights: Ideas for Advantage

💰 Practice Makes Profit:

Rich challenges leaders to take a strategic pause and think about their career evolution — not just where they are, but where they want to go.

He outlines a simple framework used with executives to guide this reflection. Rich reminds listeners that effective leaders design their future, building each career move as a deliberate step toward their end game.

🧠 League of Strategic Minds:

This listener's question: “What should a one-page business plan include?”

Rich recommends creating a StrategyPrint — a clear, one-page snapshot of how your business creates value. He also suggests including your purpose, mission, vision, and values at the top to keep your plan anchored in intent.

Listeners can submit their own questions at StrategySkills.com for a chance to be featured — and win some Strategic Minds swag.

🏆 Winsights:

Rich closes with a Winsight — an idea for advantage — from Cal Henderson, co-founder of Slack, who asks:

“What are the things that are most strategically important — and am I allocating my time to them correctly?”

It’s easy for leaders to get lost in the weeds. Rich reminds teams to step back and structure their discussions around what truly drives the business forward.

If your meetings are filled with tactics, your organization will stay tactical. Strategy begins with how you spend your time.

🔗 Links:

📘 AI and the Octopus Organization: Building the Superintelligent Firm: Amazon Link

📘Costovation: Innovation that Gives Your Customers Exactly What They Want–and Nothing More: Amazon Link

📘 The Innovative Leader: Step-by-Step Lessons from Top Innovators For You and Your Organization: Amazon Link

📘 Jobs To Be Done: A Roadmap for Customer-Centered Innovation: Amazon Link

💼 Stephen Wunker on LinkedIn: linkedin.com/in/stephenwunker

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The Octopus Approach to AI

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