E530 – Derek Crager, Practical AI: How to Keep Your Best Employee Forever
“If we leverage AI to give us the information we need, when we need it, we can solve and resolve our situations more quickly.”
When Derek Crager left Amazon, it wasn’t to chase the next flashy AI trend. It was to solve a deeper, more human problem: how to make learning more accessible, inclusive, and adaptable for real people in real jobs. Derek explores the creation of Pocket Mentor, a voice-powered AI tool that acts less like a chatbot and more like a thoughtful guide. Built with neurodiversity in mind and designed to reduce friction in learning, Pocket Mentor helps people develop leadership skills, navigate workplace challenges, and get unstuck—when they need it most. Derek shares how his experiences at Amazon shaped his understanding of simplicity and scale, and why he believes we’re at a fork in the road with AI. Will we use it to empower or replace? Connect or control? This conversation is an invitation to think deeper about the future of work, learning, and human-machine collaboration.