Design Thinking 101

• 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 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

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• Operational Excellence in Design + Leadership + Design Ops with Jon Fukuda — DT101 E144

  Jon said that when he first discovered the design operations community at the 2019 Design Ops Summit in Brooklyn, it felt like coming home. Here was this entire tribe of people who cared about the same things he’d been passionate about for years—creating systems that help designers do their best work. In this episode, I'm talking with Jon Fukuda, co-founder of Limina.co, about how design operations has evolved from an unnamed set of practices into a vital discipline that drives organizational excellence. As organizations continue to face economic pressures, the conversation around design operations has become more critical than ever. How do we demonstrate the strategic value of design teams? How can operational excellence serve not just designers but business outcomes? Jon shares insights from his 20+ year journey—from early days defining UX practice models to his current role as a design ops leader and community builder. This conversation reveals how the best design operations leaders think beyond tooling and process to focus on team health, cross-functional partnerships, and systems that elevate both human-centered practices and business innovation. Whether you're considering a move into design ops or looking to strengthen your design leadership approach, Jon's practical wisdom offers a roadmap for driving operational excellence in complex organizations. Questions you'll be able to answer after listening: How might we structure the first 30-60-90 days in a new design operations role for maximum impact? What key misconceptions about design operations could undermine your effectiveness as a leader? When should design ops be positioned under product teams versus operating as a horizontal function? Why do organizations often view design teams as expendable during economic downturns, and how can we change that perception? How can design operations leaders demonstrate their impact on both team health and business outcomes? About Jon Fukuda Jon Fukuda is co-founder of Limina.co with over 20 years of experience as a user experience specialist. With expertise in UX strategy, design thinking, and UI design, Jon has led teams through human-centered requirements gathering, strategy development, interaction design, testing, and evaluation. His career journey started in the late 1990s when "user experience" was just being defined, giving him a unique perspective on how design practices have evolved. Most recently, Jon has dedicated his efforts to research and design operations facilitation for scalable, sustainable human-centered systems. His passion for operational excellence makes him a respected voice in the design ops community. Episode Highlights [01:30] Jon's journey began when "user experience" was just being defined [02:10] Early exposure to coordinating UX work alongside business analysts and technologists [03:40] "I always approached with a continuous improvement mindset - learn from mistakes, get better" [04:50] The shift from individual excellence to system-level operational thinking [06:40] Jon's team started defining specialized roles: information architects, interaction designers, visual designers [08:40] On discovering the term design ops, "This is the work I've been doing for years - I just didn't have a word for it" — Jon [10:00] The North Pacific Gyre metaphor: design ops managers pick up tasks no one else claims [11:10] The community focuses on team health and infrastructure that supports practitioners [12:20] Design ops handles everything from licensing software to managing team dynamics [14:40] Different maturity levels: from surface-level design to strategic human-centered integration [16:10] How design ops prevents team burnout and toxic workplace dynamics [18:30] First steps for new design ops leaders: conduct a listening tour with your design team [19:40] "Design operations is a servant leader role - you make sure people feel taken care of" — Jon [21:30] Expand your listening tour to horizontal and vertical stakeholders to identify friction points [22:40] The necessity of executive sponsorship when conducting large-scale assessments [24:30] Building a shared vision of success that aligns stakeholders around design operations [26:40] Design ops spans program management, infrastructure, HR partnerships, and career development [27:00] Common misconception: reducing design ops to just design systems or program management [29:40] Challenges of positioning design operations within product-led organizational hierarchies [31:00] Why siloing design teams under product lines limits cross-organizational learning [32:00] The Design Ops Assembly Slack community as a primary resource for practitioners [34:40] Recommended resources: Nielsen Norman article and the Design Conductors book [36:10] Design Ops Assembly Learning Labs offer stratified professional development programs [38:40] Economic challenges lead organizations to view designers as expendable despite their value [41:40] "The future requires better integration - both process and tooling" — Jon [42:10] Need for better connections between design tools and broader business systems   Questions to Help You Go Deeper Learning What surprised you most about the spectrum of activities that fall under design operations, and why? How does the concept of operational excellence in design challenge or enhance your current understanding of design leadership? Which aspects of the listening tour methodology seem most valuable for your context? Leading How might you help your team understand the connection between operational excellence and strategic business outcomes? Where in your organization would improved design operations create the most immediate value? What would success look like if you implemented a structured listening tour with your horizontal and vertical stakeholders? Applying What's one small experiment you could run next week to improve an operational aspect of your design practice? Which current friction points in your team's workflow could be addressed using design operations principles? How could you adapt the first 30-60-90 days framework to fit your specific organizational context?   Practicing How will you build stakeholder relationship management into your regular practice? What support or resources do you need to implement better integration between your design tools and broader organizational systems? Who could you partner with to practice articulating the business value of your design operations initiatives? Resources Nielsen Norman Group Design Ops 101 - An excellent primer that defines design operations as "the orchestration and optimization of people, processes, and craft in order to amplify design's value and impact at scale." The Design Conductors - A new comprehensive book by Rachel Posman and John Calhoun from Salesforce, providing guidance on building DesignOps programs. Patrizia Bertini's Website - Jon recommends her perspective on design ops and business value, with various articles on DesignOps strategy and measuring impact. Events Rosenfeld Media's Design Ops Summit - The premier annual conference for design operations professionals. Henry Stewart's Creative Operations + Design Operations Events - These events take place in New York, London, Los Angeles and other cities, often featuring co-located Design Operations Symposiums. Deepen Your Learning Operations + Human Centered Design + Art with Alvin Schexnider — DT101 E116 - Explores the intersection between operations, human-centered design practices, and artistic approaches to problem-solving, providing additional context for operational excellence in design organizations. Creating a UX Career with Sarah Doody — DT101 E77 - Offers insights into career development for UX professionals that complements the discussion on design operations leadership and team development. Ask Like a Designer — DT101 E61 - Introduces the six designer voices (Builder, Scout, Tinker, Facilitator, Traveler, and Pro) that can help design operations leaders develop a more comprehensive approach to supporting their teams and driving excellence.

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