IT Horror Stories with Jack Smith

Shadow IT Reports


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We dive into the familiar chaos of Shadow IT created by the sales department — well-intentioned, fast-moving, and completely invisible until something breaks. A "quick tool" turns into a critical system overnight, contracts appear after go-live, and IT is asked to secure, integrate, and support something it never approved or even knew existed. It's a story about speed versus control, good intentions with bad outcomes, and why Shadow IT doesn't start with malice — it starts with urgency.

00:00 Podcast Kickoff 01:11 What is Shadow IT 02:44 Sales Server Disaster 12:57 Data Migration Drama 23:45 Luck and Lessons 25:15 Common Shadow IT 26:58 Management Irony 28:02 Final Thoughts

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IT Horror Stories with Jack SmithBy Jack Smith