Leadership, AI, and Cybersecurity I Craig Taylor

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

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