
Leadership, AI, and Cybersecurity I Craig Taylor
From 40% Better - Engineering Leadership by Bill
June 5, 2026 · 48 min
About this episode
Bill Lennan interviews Craig Taylor about leadership and cybersecurity, exploring effective training methods and the role of AI tools.
In this episode of 40 Percent Better, Bill Lennan sits down with Craig Taylor, CEO and Co-Founder of CyberHoot, to talk about leadership, cybersecurity, communication, and the power of positive reinforcement in workplace training. Craig shares his journey from early leadership experiences and public speaking failures to building a cybersecurity company focused on making security awareness engaging, human, and effective. The conversation dives into leadership lessons, root cause problem solving, social anxiety, Toastmasters, AI tools like ChatGPT and Claude, and why most cybersecurity training fails employees. You’ll also hear how CyberHoot is changing the way organizations approach cybersecurity awareness through gamification, behavioral psychology, and educational design. Topics covered: • Leadership lessons from failure • Public speaking and overcoming social anxiety • Root cause analysis in tech leadership • Cybersecurity awareness training • Positive reinforcement vs punishment culture • AI tools for writing and productivity • ChatGPT vs Claude • Building company culture in tech • Psychology and behavior change • Entrepreneurship and startup growth About the Guest: Craig…
People in this episode
Host: Bill Lennan
Guest: Craig Taylor
Topics covered
- leadership
- cybersecurity
- communication
- positive reinforcement
- AI tools
- entrepreneurship
- behavioral psychology
Keywords
- leadership lessons
- cybersecurity training
- social anxiety
- AI tools
- gamification
- behavior change
- entrepreneurship
Mentioned in this episode
Organizations: CyberHoot
Products: ChatGPT, Claude
More episodes of 40% Better - Engineering Leadership
- Building Trust Through Leadership I Dave Bair · June 12, 2026 · 33 min
- Leadership Through the Power Leadership Through the Power of Story I Gavin McMahonof Story I Gavin McMahon · May 29, 2026 · 46 min
- Friction Free Leadership That Works I Jimmy Burroughes · May 22, 2026 · 41 min
- Why Human Leadership Still Wins in the Age of AI I Joshua Gould · May 15, 2026 · 52 min
- Leadership, Power, and Real Growth at Work I Charley Wedeen-Zittle · May 8, 2026 · 1h 6m
- Leadership Without a Title in Tech I Juan Boyce · May 1, 2026 · 39 min
Explore listener stats, chart rankings, contacts and more on the 40% Better - Engineering Leadership podcast page.