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When Strategy Meets Security: Glenn Wilson on Technical Debt, Developer Voice, and Defensive Thinking
Manage episode 503904651 series 3657827
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/
Chapters
1. Introduction to Cybersecurity and Leadership (00:00:00)
2. The Current State of Cybersecurity Strategy (00:02:45)
3. Balancing Short-Term and Long-Term Security Goals (00:05:09)
4. Understanding Technical Debt in Development (00:07:10)
5. The Disconnect Between Business Leaders and Developers (00:09:25)
6. The Importance of Inputs and Outputs in Development (00:11:13)
7. Engaging Developers in Tool Selection (00:12:40)
8. Measuring the Value of Cybersecurity (00:15:40)
9. The Cost of Cybersecurity and Its Perception (00:17:59)
10. Compliance vs. Quality in Cybersecurity (00:19:53)
11. Empowering Developers for Better Security (00:21:53)
12. Commander's Intent in Cybersecurity (00:23:11)
13. Defensive Security and Incident Management (00:24:53)
14. Chaos Engineering in Cybersecurity (00:26:55)
15. Outcome-Based Learning in Security Training (00:28:11)
16. Building Resilience in Cybersecurity (00:29:28)
17. The Importance of Training and Communication (00:34:46)
18. Understanding the OODA Loop in Cybersecurity (00:41:52)
19. Exploring Vulnerability Management Systems (00:44:28)
20. Fostering Joy and Creativity in the Workplace (00:50:56)
21. Outro (00:54:28)
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