When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 employees and became the subject of a Harvard Business School case study, the documentary The Loop, and coverage in the New York Times and Fortune.

We explore how culture drives outcomes, why the team is the atomic unit of change, and how to design a leadership structure that earns trust and creates momentum. Phil brings sharp insight, rich stories, and practical frameworks drawn from a 45-year career spanning startups, scale-ups, and global enterprises. If you’re leading change—or trying to get others to believe in it—this conversation is your blueprint.

Phil Gilbert is best known for scaling IBM’s global design transformation. He was inducted into the New York Foundation for the Arts Hall of Fame in 2018 and named an Oklahoma Creativity Ambassador in 2019. Since retiring from IBM in 2022, Phil has focused on helping business and military leaders shift culture at scale to improve innovation and team performance.

Key Takeaways

• Culture is the system: Real transformation means rewiring people, practices, and places—not just teaching new skills.
• Teams are the atomic unit of change: Change doesn’t scale through individual mandates. It scales when cross-functional teams deliver new outcomes.
• Design scales empathy: Phil shares how design thinking isn’t just about aesthetics—it’s a tool for scaling understanding and improving systems.
• Transformation needs protection: Change teams need structural support and a leadership “shell” that shields them while engaging the broader org.
• Momentum beats mandates: Leaders can’t impose change—they must earn it by showing results, listening deeply, and integrating across silos.

Additional Insights

• "Every day is a prototype": Phil’s mantra that gives teams permission to change, test, and learn continuously.
• The virus model of leadership: To spread new ways of working, Phil designed his leadership team like a virus—with spikes into HR, finance, comms, and IT.
• Designers aren’t the barrier—systems are: In companies with weak design reputations, the problem isn’t the designers. It’s the culture around them.
• Shadow IT kills transformation: Real progress happens when change leaders partner with CIOs—not work around them.
• Most AI efforts are missing the point: Phil argues that AI transformation fails when it focuses on individuals instead of improving team-level outcomes.

Episode Highlights

00:00 - Episode Recap

Barry O’Reilly recaps the episode’s theme, discussing leadership challenges, reclaiming strategic focus, and leveraging frameworks, executive habits, and AI to drive impactful business outcomes.

2:26 - Guest Introduction

Barry introduces Phil Gilbert, renowned for leading a major cultural transformation at IBM through human-centered design. He previews Phil’s new book, “Irresistible Change,” and sets expectations for a discussion on leadership, empathy, and executing change at scale.

3:21 - Official Start of Conversation

Phil Gilbert reflects on pivotal career moments, including his experience founding early startups, the challenge of driving adoption for new technologies, and discovering the power of empathy and design. He introduces his guiding philosophy, “every day is a prototype.”

9:15 - The Power of Prototyping and Embracing Change

Phil explains how prototyping and a willingness to challenge the status quo lead to organizational and personal growth. He shares his “every day is a prototype” mantra and stresses the role of openness in innovation.

13:48 - Culture as a Driver of Outcomes

Phil outlines his formula for driving real change, focusing on people, practices, and places. He discusses his use of journaling and intentional observation to systematically build curiosity and support for change in teams.

20:47 - Designing Transformation at Scale

Phil discusses the challenge of leading IBM’s company-wide design movement. He explains his strategy to reach and influence 400,000 employees and the importance of building a diverse leadership team to support transformative efforts.

31:29 - Practical Tactics for Organizational Change

Phil details the need to integrate HR, tooling, and communications into the transformation process, sharing stories about revamping career ladders and piloting new tools. He emphasizes collaboration and transparency with key stakeholders like HR and CIOs.

37:51 - Lessons for Modern AI Transformation

Phil and Barry examine current challenges with AI change efforts, arguing that teams—not just individuals—are the fundamental units for successful transformation. They discuss why team-level outcomes should guide measurement and strategy for adopting new technologies.

41:09 - Hopes and Irresistible Change for the Future

Phil shares his vision for the next wave of business transformation, especially regarding AI. Drawing inspiration from cloud computing’s impact, he hopes leaders will adopt principles that empower teams to drive industry-defining change.

Useful Resources

• Phil Gilbert – Irresistible Change (book): Buy on Amazon
• Connect with Phil on LinkedIn: Phil Gilbert
• Barry’s blog on AI

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