Episode 183 - Designing What’s Next, Rewiring Work, and Apple’s Innovation Crossroads

Episode 187 - Your Questions, My Answers

This week on Shape of Tomorrow, I'm taking a different approach and answering questions submitted by listeners and readers. We explore how organizations can build trust in their data, separate AI reality from marketing hype, prioritize the right initiatives, and connect technology investments to meaningful business outcomes. If you're navigating the challenges of strategy, innovation, data, or AI, this episode offers practical perspectives and frameworks to help you make better decisions with greater confidence.

Episode 186 - The Great Repatriation

This week on Shape of Tomorrow, I explore what I’m calling The Great Repatriation, the quiet but potentially massive shift of AI away from the cloud and back toward organizations themselves. Most people see this as another hardware announcement. I think it points to something far more important. In this shorter episode, I unpack why AI sovereignty, local intelligence, and owning your own “AI factory” may become one of the most important strategic decisions organizations make over the next few years.

Episode 185 - Building an AI Roadmap When Budgets Are Tight

In Episode 185 of Shape of Tomorrow, I explore the growing disconnect between the AI conversations happening at conferences and the realities organizations are facing inside boardrooms and budget meetings. I break down how I think leaders should approach AI roadmaps when budgets are constrained, pressure is high, and credibility matters more than hype. I walk through a practical framework focused on small, measurable experiments that can prove value within 90 days, rather than massive multi-year transformation initiatives. Along the way, I discuss KPI-driven thinking, sponsorship, data readiness, pilot design, and how organizations can build long-term AI capability through disciplined experimentation and strategic focus.

Episode 184 - Why Successful Organizations Still Miss the Future

In this episode of Shape of Tomorrow, I explore why so many successful organizations still struggle to adapt when disruption begins at the edges. Drawing from ideas in my upcoming book Strategic Surface Area, I walk through three practical actions leaders can take to avoid falling into the innovator’s dilemma and build organizations that are better at detecting signals, protecting experimentation, and responding to change before it is too late. I also dive into a fascinating new development from Anthropic around AI memory and “dreaming,” and why I believe the future of artificial intelligence may depend less on raw intelligence and more on how systems manage continuity, context, and memory over time. I unpack what happens when AI agents evolve across thousands of interactions and why memory architecture could become one of the most important battlegrounds in AI.

Episode 183 - Designing What’s Next, Rewiring Work, and Apple’s Innovation Crossroads

In this episode, I explore three timely and thought-provoking topics shaping how we think about the future of work, education, and innovation. I begin with entrepreneurship in schools, unpacking why there is strong agreement on its importance, yet so many programs struggle to take hold. The real challenge is not belief. It is design. Next, I examine Amazon’s recent hiring and layoffs, and what it reveals about how organizations are redefining talent in an AI-driven world. This is not contraction. It is a shift toward a different kind of workforce. Finally, I take a closer look at Apple through the lens of the innovator’s dilemma, exploring what happens when a company known for disruption must confront the risk of disrupting itself. Three distinct conversations, each offering insight into how change is unfolding across institutions and industries.