Charlene Li - Winning with AI

Diana Wu David - Multi-Stack Transformation

Diana Wu David, Director of Futures at ServiceNow and a top-ranked global futurist, discusses the radical "multi-stack transformation" facing organizations in 2026. Diana explores the stark divide in AI optimism between the East and West, and how this cultural sentiment shapes global adoption. She also outlines a roadmap for leaders to move past "pilot purgatory" by adopting a "strong, fluid stance" — balancing stable, deterministic workflows with the generative potential of AI. The conversation focuses on how the C-suite must now coalesce to orchestrate an agentic workforce, onboarding digital employees and pivoting human talent into high-value revenue streams that were previously unimaginable.

Telisa Yancy - Future of Insurance and the Impact of AI

Telisa Yancy discusses the future of insurance in the rapidly evolving digital and AI-driven world. She highlights the significance of insurance as a crucial purchase for individuals and families and the opportunities for transformation in the industry. Telisa emphasizes the role of data and real-time processing in providing more customer-driven insurance solutions. She envisions traditional lines of insurance becoming smarter and more capable of insuring assets on the fly with minimal information. We also discuss the potential for proactive risk prevention and the need for a balance between privacy and data usage.

Sarah Fay - The Future of Personal Data

Sarah Fay discusses the topic of personal data ownership and the importance of individuals having control over their own information. We explore the challenges of data privacy and the potential risks of data breaches. The conversation also touched upon the role of regulations like GDPR in protecting individuals' data rights. We considered the benefits and drawbacks of companies buying and selling data, highlighting the potential for exploitation and the need for transparency and consent. The ethical implications of monetizing personal data were raised, including concerns about fairness and the potential for discrimination. The conversation also touched upon the role of artificial intelligence in data analysis, discussing the potential for algorithmic biases.

Charlene Li - Winning with AI

Charlene Li, New York Times bestselling author and business transformation expert, joins the podcast to provide a strategic masterclass on navigating the AI transition. As the co-author of the new book Winning with AI: The 90-Day Blueprint for Success, Charlene argues that the current 87% failure rate in enterprise AI projects stems from treating the technology as a "hammer looking for a nail" rather than a transformational business initiative. The conversation dives deep into the practical frameworks required to move beyond aimless "pilot purgatory". Charlene breaks down the necessity of "Goldilocks Governance" and explains why the next year will see a massive explosion of "embodied AI" through an agentic workforce. From the "forensic re-examination" of broken business processes to the shift toward "AI fluency" as a core leadership trait, this episode serves as a vital guide for leaders looking to generate measurable business value from AI within a data-saturated world.

Melissa Grady - The Motor Industry's Future Opportunities

Melissa Grady, former CMO of Cadillac, discusses the motor industry's past, present, and future, focusing on the legendary automaker's 118-year DNA of innovation—from the first electric starter to modern hands-free driving—and how it is now accelerating toward a "full-on" EV reality. Grady also lays out a vision for the future of the luxury vehicle industry, where personalization, sustainability, and digital intimacy define the modern driving experience.