S6 E4 - Glenn Wilson – Rethinking Cybersecurity Through Systems Thinking

In this episode, Glenn Wilson, a cybersecurity expert, joins me to explore how systems thinking can reshape how we approach cybersecurity, vulnerability management, and modern digital systems.

Glenn shares his journey from writing about DevSecOps to pursuing a master’s degree in Systems Thinking in Practice at the Open University. His motivation came from recognizing a troubling contradiction that, despite massive investments in cybersecurity, data breaches, ransomware incidents, and security failures continue to rise. This led him to question whether the industry’s largely reductionist approach misses the broader system dynamics at play.

A central part of the discussion focuses on Stafford Beer’s Viable System Model (VSM), a cybernetic framework for understanding how organizations maintain balance and adapt to their environments. Glenn explains how VSM’s five subsystems can be used to diagnose why cybersecurity systems often fail. Rather than viewing security as a set of tools or controls, Glenn argues it should be understood as a living system embedded within larger organizational and risk systems.

The conversation then expands into cybernetics, emergence, and AI, touching on Norbert Wiener, Ross Ashby’s law of requisite variety, and John Boyd’s OODA framework. Together, we discuss how feedback loops, adaptation, and emergent behavior shape both human organizations and AI-driven systems. Glenn raises an important concern: if organizations don’t adopt systems thinking, increasing automation and AI could amplify weaknesses rather than solve them.

We close by reflecting on the relationship between humans, AI, and complex systems. Glenn emphasizes that AI should be treated as a tool within a larger system, not anthropomorphized as human intelligence. The key challenge ahead is understanding how humans and intelligent tools coexist within systems that are adaptive, emergent, and increasingly complex.

The big takeaway: cybersecurity cannot be improved by optimizing isolated parts. Real progress requires understanding the entire system and our place within it.