Iterate Like a Craftsman: The Bob Dylan Reminder

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Phil Gilbert joins Joe for a masterclass on leading lasting change—how to move large organizations, overcome cultural antibodies, and build systems that make transformation stick.

As the former head of design at IBM, Phil was tasked with one of the most ambitious corporate transformations of the last decade: to reignite creativity, collaboration, and speed inside a century-old company known for its consistency. Drawing from his new book Irresistible Change: A Blueprint for Earning Buy-In and Breakout Success, he shares the playbook that helped shift IBM’s mindset from compliance to commitment—and what leaders in any field can learn from that journey.

In this conversation, Joe and Phil unpack what it really takes to drive change at scale: how to earn voluntary adoption instead of forcing compliance, why culture must evolve alongside strategy, and how language, branding, and storytelling can make or break a transformation. They explore lessons that resonate from boardrooms to battlefields—how to lead people through uncertainty, protect the integrity of a mission, and create a culture that thrives on iteration and learning.

Listeners will come away with an actionable framework for driving change—one rooted in human behavior, organizational design, and the power of intentional leadership.

In this episode, Joe and Phil also explore:

• Why the status quo is resilient—and how great organizations learn to challenge it continuously
• How IBM’s “Hallmark” program turned change into a desirable brand, not a mandate
• The formula behind lasting culture: people + practices + places
• Why forcing compliance breeds “antibodies,” and how to inspire genuine belief instead
• How storytelling and small-team “boot camps” made transformation go viral inside a 400,000-person company
• The role of senior leaders in rewarding behavior and reinforcing new norms
• What the “magic people” and The Captain Class teach us about influence from within teams
• Why great leaders think like designers—iterating, prototyping, and refining as they go

Whether you’re leading a military unit, a corporate team, or a creative project, this episode offers a field-tested blueprint for driving change that lasts—one built on empathy, clarity, and a deep respect for the craft of leadership.

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