Episodes / #92

What You Don't Know About Your Email

September 9, 2026 · 48:15
Guests: Craig Taylor

Craig Taylor, co-founder of CyberHoot, explains why fake phishing tests that end in a meeting with HR can backfire, and how positive reinforcement helps employees spot real attacks.

Topics Covered

CybersecurityEmail SecuritySecurity AwarenessSmall BusinessThe Web Talk Show

Show Notes

Armando J. Perez-Carreno talks with Craig Taylor, co-founder of CyberHoot. Most companies test their staff by sending fake phishing emails and tracking who clicks. Craig has spent 30 years in cybersecurity, and he thinks that approach often backfires.

Craig came into security through a psychology degree, before the world wide web existed. He explains what happens when an employee fails a phishing test and ends up in a meeting with HR: they learn to resent the IT department, and they get no better at spotting the next attack. He also walks through how positive reinforcement changes that outcome. If you’re responsible for keeping a team safe from email scams, this one gives you a better way to train them.

Topics Covered

  • Why punitive phishing tests can backfire
  • How a psychology background shaped Craig’s approach to security
  • What happens when a failed phishing test turns into an HR meeting
  • How positive reinforcement helps employees spot real attacks