Episode 93: Practical Zero Trust, Apprenticeships, and Learning to Learn in the Age of AI

Guest: Larry Woods

Every breach has a story. Every leader has a strategy.

In this episode of The Professional CISO Show, host David Malicoat sits down with Larry Woods, a seasoned cybersecurity executive, during the St. Louis stop of the U.S. Tour for a wide-ranging and deeply practical conversation about what it really takes to lead cybersecurity at scale.

This is not a theoretical discussion. It’s a grounded, experience-driven dialogue focused on execution, leadership maturity, and the realities CISOs face every day.

Larry shares his personal journey from early technology exposure through infrastructure leadership and into the CISO role, highlighting how security has quietly become embedded in nearly every aspect of modern IT. From there, the conversation expands into three critical areas shaping the future of the profession.

🔐 Practical Zero Trust — Not the Buzzword Version

Zero Trust is often dismissed as unattainable or overly complex. Larry challenges that narrative by reframing Zero Trust as a series of pragmatic, achievable decisions rather than a perfect end state.

He explains how removing users and devices from the traditional network, leveraging secure access paths, and embracing cloud-first and SaaS-first strategies can dramatically reduce breach impact. Rather than chasing perfection, the focus is on measurable risk reduction and resilience — a perspective every modern CISO needs.

👩‍💻 Building Cyber Talent Through Apprenticeships

Larry also dives into one of the most actionable talent strategies discussed on the show: cybersecurity apprenticeships.

Instead of short-term internships that rarely deliver meaningful impact, Larry outlines how long-term, part-time apprenticeships allow organizations to develop junior talent over multiple years. The result is stronger technical capability, deeper cultural alignment, and a pipeline of professionals who truly understand the business — not just the tools.

For CISOs struggling with hiring, retention, and entry-level readiness, this segment alone is worth the listen.

🧠 Learning to Learn in the Age of AI

One of the most thought-provoking segments of the episode centers on a question few leaders are asking out loud:

What happens to critical thinking when AI always has the answer?

Larry and David explore the difference between using AI as a shortcut versus using it as an accelerator for learning. As AI reshapes how work gets done, the ability to learn how to learn becomes a defining leadership skill — especially in cybersecurity, where context, judgment, and reasoning still matter.

This conversation connects AI, education, leadership development, and the future CISO skill set in a way that is both reflective and practical.

🏛️ From Technologist to Executive Leader

Larry also shares candid insights on:

• The moment a CISO truly becomes an executive: the first board presentation
• Why leadership teams matter more than company brands
• Leading through influence in decentralized organizations
• The value of business education for cybersecurity leaders
• Why today’s CISO must be fluent in risk, communication, marketing, legal concepts, and board dynamics

The episode closes with a personal and revealing “10 Questions” segment that offers a glimpse into Larry’s mindset beyond the title.

🎧 Why You Should Listen

If you are:

• A CISO navigating Zero Trust, cloud, and board expectations
• A security leader building teams and future talent
• An aspiring CISO trying to understand what the role really demands
• A cybersecurity professional thinking about AI’s long-term impact

This episode will resonate.

🔗 Listen, Watch, and Connect

• 🎥 Watch the episode: http://www.youtube.com/@TheProfessionalCISO
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• 🍎 Apple Podcasts: https://podcasts.apple.com/us/podcast/the-professional-ciso/id1731138021
• 🌐 Website: https://www.thpc.co
• 🔗 LinkedIn: https://www.linkedin.com/company/the-professional-ciso-show

📣 Call to Action

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