Leadership & Strategy + Fighter Pilots + Design Education with Jason "TOGA" Trew — DT101 E145

When I first connected with Jason Trew (callsign: TOGA), I knew this conversation would challenge some assumptions about where design thinking belongs. Jason is an Air Force fighter pilot and strategy leader turned professor. What emerged from our conversation wasn't just another story about design thinking adoption, but a deeper exploration of what he sees happening when we distinguish between capital-D Design Thinking and lowercase-d design thinking, and why that distinction matters for everyone trying to create meaningful change. Jason's journey from F-15 pilot to design educator reveals something crucial about how design thinking transforms not just what we do, but who we become as problem solvers. His work with thousands of Air Force officers, his deployment experiences in classified operations centers, and his current role (*at the time of recording) teaching at the Savannah College of Art and Design (SCAD) offer unique insights into how design thinking functions when the stakes are genuinely high. Listen to Learn About: What's the critical difference between capital-D Design Thinking and lowercase-d design thinking, and why does this distinction matter for practitioners?How can design thinking principles function effectively in highly structured, high-stakes environments where traditional approaches dominate?What role does psychological safety ("feeling safe, supported, and stretched in meaningful ways") play in enabling creative problem-solving?How do we balance the need for systematic approaches with the emergent, integrative nature of actual design work?When should leaders prioritize conditioning people into a "ready stance" versus teaching specific design methods? Our Guest Col Jason "TOGA" Trew (US Air Force, retired) represents a fascinating intersection of military leadership, academic rigor, and design practice. After graduating from the U.S. Air Force Academy and flying F-15s, Jason spent his final military decade revolutionizing how the Air Force approaches strategy education and leadership development. He earned a PhD in the history of technology, served as Dean and Vice Commandant of the Air Force Leadership School, and led design teams for Space Force education initiatives. Now a Professor of Design* Management at the Savannah College of Art and Design, Jason brings a unique perspective on what happens when design thinking meets organizational realities where failure isn't an option. (*At the time of recording.) Episode Highlights [02:10] Jason's journey from F-15 fighter pilot to design educator through strategy school and a PhD in technology history [03:30] Discovery of a book dedicated to Icarus as hero rather than cautionary tale, sparking interest in playfulness complementing practicality [04:20] How design thinking became curriculum at Air Force Leadership School serving 4,000 students annually [05:10] Jason's certification in Lego Serious Play for facilitating innovation sprints and strategic thinking workshops [07:20] The crucial distinction between capital-D Design Thinking and lowercase-d design thinking [09:00] Capital-D focuses on activities and checklists; lowercase-d develops embodied sensibility for knowing what to do next [11:40] Design thinking as conditioning people into a ready stance for handling surprise rather than teaching linear processes [13:00] Why Jason believes design thinking changes the people involved, with problem-solving as bonus rather than primary goal [14:40] How design thinking shifts perception to see multiple options beyond binary choices [15:30] Jason's approach to ambiguous assignments that allows students to surprise him with creative solutions [17:30] Learning design principles that avoid constraining student intelligence for the sake of rigid academic standards [18:50] Design thinking's spillover effects on leadership and education beyond formal design practice [22:40] Design thinking as fundamentally human activity connected to living well and building better communities [25:10] Coffee shop door story illustrating how design changes your eyes to see problems everywhere [26:40] Design as integrative discipline that's undisciplined in the best academic sense [28:40] Framework of design as expedient - practical, opportunistic, and contextual rather than optimal [30:00] Why expedient design requires ethical sensibility to guide this human superpower responsibly [32:30] Jason's faith that if we designed current systems, we can design something better [36:40] Deployment story of creating psychological safety in classified military operations center [38:30] Using Lego as thermoplastic polymer strategic thinking tool to overcome initial skepticism [39:00] Daily check-ins asking team members if they feel safe, supported, and stretched in meaningful ways [41:10] Danger of treating organizational roles as reality rather than abstractions of actual people [43:30] Failed redesign of Air Force Leadership School and lessons about empathy work threading ...