Strategy Meets Reality Podcast When Strategy Meets Security: Glenn Wilson on Technical Debt, Developer Voice, and Defensive Thinking
Cybersecurity isn’t just about protecting data—it’s about enabling execution under pressure.
In this episode of Strategy Meets Reality, Mike Jones is joined by Glenn Wilson—cybersecurity expert, OODA loop practitioner, and founder of Dynaminet—to explore how the challenges of security mirror those of strategy. From technical debt to tool overload, commander's intent to learning loops, they unpack how poor decision-making, misaligned incentives, and lack of feedback erode both resilience and execution.
This is not a technical talk. It’s a strategy conversation about where things break—and what to do about it.
🔍 In this episode:
- Why strategy and cybersecurity face the same execution challenges
- The hidden cost of technical debt and over-engineering
- Why developer voice matters for resilience and tooling
- Using OODA and chaos engineering to build adaptive responses
- What commander's intent looks like in security
- How to embed security without killing innovation or joy
🎧 Keywords: Strategy Execution, Cybersecurity, OODA Loop, Technical Debt, Developer Experience, Chaos Engineering, Mission Command, Distributed Decision-Making, Leadership, Resilience
📘 Learn more: https://dynaminet.com
📬 Connect with Glenn: Glenn Wilson on LinkedIn
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🔗 Full episodes, show notes, and resources: https://www.lbiconsulting.com/strategymeetsreality-podcast
📺 Watch on YouTube → https://www.youtube.com/@StrategyMeetsReality
🎧 Listen on Spotify, Apple Podcasts, and Buzzsprout
💬 Connect with host Mike Jones → https://www.linkedin.com/in/mike-h-jones/