How to Mentor IT Teams and Troubleshoot Like a 50-Year Database Veteran

Every IT team gets the same call: "the system is down." It's a description, not a problem — and the engineers who can tell the difference are the ones who keep systems running. In this episode, Jay and Michael welcome back fan favorite Rick Goudeau, employee number two at Clear Winds and a database specialist with over 50 years in technology dating back to the 1970s. Rick has spent his career on Oracle E-Business Suite upgrades, disaster database recoveries, and the kind of thorny problems that don't show up in vendor documentation. In "Tales From the Old Timer," he breaks down the specific behaviors that made him effective — thinking like a diagnostician, working methodically, staying relentlessly curious — and why mentoring the next generation is the part that lasts. This is a practical, no-BS conversation for IT directors, CIOs, DBAs, systems engineers, and anyone responsible for building a team that can troubleshoot without them in the room. 🚀 In this episode: Why "the software doesn't work" is a description, not a problem — and how to get to the real issue The Sherlock Holmes principle Rick has used for 50 years: eliminate the impossible, and notice the dog that didn't bark Why being methodical doesn't mean being slow — and how documenting 200-300 step Oracle upgrades pays off years later Why roughly 60-70% of IT problems are understanding issues, not technical ones The WordPress fix that worked — and why the right engineer refused to stop at "it works now" How an AI model change quietly slowed down a working application, and what that reveals about AI as a starting point vs. an ending point Recovering a production database that was accidentally deleted — and the mentoring moment that came out of it The reboot that didn't come back up, and why staying calm in front of the person shadowing you matters more than the fix Why mentoring has to be organic, not something you do because you're a director or manager The intern who bought Rick a mug 40 years ago — and why he's still using it Rick's parents, two walls of books, and the reason he was never allowed to say "I'm bored" Why the goal is building people who can pass you, not people who need you If you've ever been the only person who knew how to bring the system back up — this episode is for you. 🎯 Timestamps: 00:00 Welcome Back Rick 01:12 Career Recap Setup 03:16 Diagnostician Mindset 05:00 Methodical Documentation 07:53 Observing the Details 09:07 Root Cause Questions 10:45 Human Skills Matter 11:41 Curiosity and Learning 14:42 AI as Starting Point 15:35 Curiosity at Home 15:59 Curiosity Builds Thinking 16:45 New Orleans Roots 16:57 Food and Culture Picks 17:31 WWII Museum Backstory 18:51 Mentoring Through Mistakes 20:42 Keeping Calm in Crises 22:09 The Mug That Mentors 23:40 Leading by Lifting Others 25:57 Retirement and Legacy 26:34 Signing Off and Where to Follow 👀 Check out the show notes: https://www.clearwinds.net/it-team-me... 🔔 Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 📲 Follow The IT Directors Podcast: LinkedIn:   / clear-winds-technologies   Instagram:   / theitdirectorspodcast   Facebook:   / theitdirectorspodcast   X: https://x.com/itdirectorspod Spotify: https://open.spotify.com/show/1FNVuJ8... Apple Podcasts: https://podcasts.apple.com/us/podcast...