In this episode, Francis Gorman sits down with Jennifer Ewbank, former CIA Deputy Director for Digital Innovation, to explore what it means to lead with purpose in a world shaped by geopolitical risk, digital disruption, and information warfare.
Jennifer shares stories from her extraordinary career in intelligence — from espionage during the Cold War to launching the CIA’s first AI office — and offers deeply human reflections on risk-taking, resilience, and transition. From the digital battlefield to the Camino de Santiago, this conversation ranges from high-stakes decision-making to how we build trust in an age of deepfakes and AI manipulation.
Takeaways
- Purpose Under Pressure: A clear sense of mission is what sustains leadership in complex, high-risk roles.
- You’ll Never Have All the Information: Good decisions often require boldness, not certainty — a lesson from field operations that applies to enterprise leadership.
- The Real Threats Are Already Inside: Critical infrastructure is increasingly compromised by cyber actors who may lie dormant for years before striking.
- Transition Is a Process: Jennifer’s solo Camino de Santiago pilgrimage was both a mental and physical journey into a post-CIA identity.
- Trust Is the New Battlefield: Generative AI, deepfakes, and algorithmic manipulation are eroding public trust at scale — and rebuilding it starts with education and digital literacy.
- Operational Mindset for Innovation: Solving complex problems quickly with limited resources isn’t just for the CIA — it’s the new model for digital transformation.
Soundbytes
- “Sometimes the greatest risk is not taking the risk.”
- “You never have all the information — expecting it is a recipe for paralysis.”
- “Absent a deep connection to purpose, you lose the urgency to solve real problems.”
- “The battlefield isn’t just physical anymore — it’s informational, algorithmic, and real-time.”
- “Trust is under attack. And the worst part is, most people don’t realize it.”
- “You think the algorithm is adapting to you. But really, you’re adapting to it.”
