Episode: Bridging Military and Civilian Cybersecurity: Leadership, Skills, and Lifelong Learning with Christopher Ross
Pub date: 2025-09-15
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In this episode, host Aaron Crow sits down with cybersecurity leader and National Guard threat hunt team lead Christopher Ross, diving into the real-world experiences that shape careers in the intersecting worlds of IT and OT security. Chris shares his 18-year journey from joining the military with a passion for computers to leading critical infrastructure cybersecurity efforts - both in uniform and in the private sector. Together, Aaron and Chris break down myths about gatekeeping, discuss the unique challenges of military versus civilian roles, and highlight lessons learned along the way.
From imposter syndrome to servant leadership, the conversation unpacks how effective communication, continuous training, and the willingness to learn from failure fuel professional growth. Chris also reflects on how military training instills risk mitigation and teamwork, and how those skills can translate - and sometimes clash - with civilian cybersecurity cultures. They talk certifications, hands-on learning, the importance of meaningful tabletop exercises, and the evolving landscape as AI powers both attackers and defenders.
Whether you’re a veteran, a fresh analyst, or just passionate about cybersecurity, this honest and energetic exchange will leave you motivated to keep learning, keep growing, and keep protecting it all. So grab your energy drink and tune in for a conversation that proves everyone in cyber, no matter their path, has wisdom worth sharing.
Key Moments:
05:30 Military Adventures Surpass Civilian Opportunities
07:28 Military vs. Civilian Leadership Dynamics
10:42 Clarifying Civilian vs Military Missions
12:22 Leadership: Addressing Miscommunication & Misalignment
15:45 Toxic Leadership and Military Transition
20:01 Reliance on Tools vs. Core Skills
22:29 "Forgotten Skills Fade Over Time"
25:13 Boosting Confidence in New Roles
29:42 Interactive Training and Environmental Protection
32:37 Purple Teaming Strategy Insights
36:15 Persistence in Skill Development
39:04 Soft Skills Matter for Career Growth
42:44 "Technical & Business Acumen Fusion"
44:41 Military: Career Value and Benefits
48:09 "Cyber Education for K-12"
Resources Mentioned :
- comprehensive resource that tracks and monitors ransomware groups and their activities.
- tracks ransomware payments by collecting and analyzing cryptocurrency addresses associated with ransomware attacks.
- real-time ransomware tracking platform that collects, indexes, and centralizes information on ra
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