I had the privilege of sitting down with Phil Howard on the You’ve Been Heard IT Leadership Podcast for Episode 412, and we went deep.

We talked about how I started out wanting to build nuclear bombs, how a training accident redirected me into computer science, and how a stint in Japan taught me the real superpower behind every technology initiative: herding cats. Getting humans to actually use what you build.

We got into the hard truths about AI. Why it’s not the panacea C-suites think it is, why vibe coding needs to stop at the prototype stage, and why the AI bubble collapse is coming faster than anyone expects. I shared the UPS story, a maintenance system that failed for years until we added change management, and broke down my framework for bringing order to chaos without mandates.

Other topics we covered:

• Why a CTO got a PhD in Industrial/Organizational Psychology
• AI security risks most teams are ignoring (package poisoning, shadow IT)
• The prototype trap, why teams leave everything in AI token loops
• Why AI won’t replace Salesforce (and what the real SaaS threat looks like)
• The shift from per-seat to per-agent licensing

If you’re leading teams, building with AI, or trying to make technology actually stick in your organization, give it a listen.

Listen to Episode 412 on You’ve Been Heard