Setting Conditions: Leaders as Gardeners

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 through entire processes

[46:00] Dawan's diagnostic questions about organizational readiness and past innovation attempts

[48:30] Strategy for identifying key voices—influencers, critics, curmudgeons, and creators—in organizations

[49:00] Power of storytelling as diagnostic tool and method for strategic thinking

[50:40] Interest in story casting and narrative intelligence using physical artifacts like Lego Serious Play

[51:00] Connection to UN Principles for Responsible Management Education and sustainable development goals

[52:40] Jason's call for partnership in bringing design skills to local and systemic governance challenges

Questions to Help You Go Deeper

Learning

• What surprised you most about Jason's distinction between capital-D and lowercase-d design thinking, and how does this change your understanding of design thinking's role in organizations?

• Which aspects of Jason's "expedient" framework for design seem most valuable for your context — the practical, opportunistic, or contextual elements?

• How does Jason's experience with ambiguous assignments challenge your current approach to giving direction or defining success criteria?

Leading

• Where in your organization would Jason's "safe, supported, and stretched in meaningful ways" framework create the most value for team performance?

• How might you help your team understand the difference between learning design methods and developing a design sensibility?

• What would success look like if you implemented Jason's approach to activating the full diversity already present in your team?

Applying

• What's one small experiment you could run next week with leaving an assignment or challenge more open-ended?

• Which current organizational challenge could you address by focusing on conditioning people's "ready stance" rather than teaching them specific methods?

• How could you adapt Jason's storytelling diagnostic approach to better understand your team's readiness for change?

Practicing

• How will you build the habit of distinguishing between roles/responsibilities (abstractions) and the full capabilities of people in those roles?

• What support or resources do you need to practice Jason's approach of setting conditions rather than controlling outcomes?

• Who could you partner with to practice the kind of empathy work Jason describes as threading through entire processes?

Resources

Books We Discussed

Experiencing Design - Jason's top recommendation for understanding how activities yield experiences that yield ways of being in the world. Liedtka, Jeanne, Karen Hold, and Jessica Eldridge. Experiencing Design: The Innovator's Journey. Columbia Business School Publishing, 2021.

Creating Wicked Students - About giving students practice with authority and ambiguity in classroom settings. Hanstedt, Paul. Creating Wicked Students: Designing Courses for a Complex World. Stylus Publishing, 2018.

Tools We DiscussedLego Serious Play - Certification and facilitation methods for strategic thinking workshops

The Archipelago of Design - Security professionals using design approaches.

COM-B Behavior Change Model - Capability, Opportunity, Motivation framework for behavior change. Michie, Susan, et al. "The Behaviour Change Wheel: A New Method for Characterising and Designing Behaviour Change Interventions." Implementation Science, vol. 6, no. 1, 2011, pp. 1-12.

Keep LearningResearch Nigel Cross and Bryan Lawson's work on how designers think.

Cross, Nigel. Design Thinking: Understanding How Designers Think and Work. Academic Press, 2011.

Lawson, Bryan. How Designers Think: The Design Process Demystified. 4th ed., Architectural Press, 2005.

Explore participatory design and co-creation methodologies.

Schuler, Douglas, and Aki Namioka, editors. Participatory Design: Principles and Practices. Lawrence Erlbaum Associates, 1993.

Simonsen, Jesper, and Toni Robertson, editors. Routledge International Handbook of Participatory Design. Routledge, 2013.

Investigate narrative intelligence

Mateas, Michael, and Phoebe Sengers, editors. Narrative Intelligence. John Benjamins Publishing Company, 2003. (Advances in Consciousness Research, vol. 46)

UN Principles for Responsible Management Education and sustainable development goals. United Nations Global Compact. Principles for Responsible Management Education. UN Global Compact Office, 2007.

Deepen Your Learning

Design Council UK + Systemic Design + Design in Government with Cat Drew — DT101 E78 Complements Jason's insights about bringing design to structured environments

Cognitive Bias + Ethics + Dreaming the Future of Design with David Dylan Thomas — DT101 E112 Works with this episode to understand different approaches to design education

Instructional Design + Adult Learning Experiences with Holly Owens — DT101 E134 Builds on Jason's themes about creating conditions for creative problem-solving