How Voice AI Helps Companies Preserve Expertise, Train Faster, and Support Neurodiverse Teams | Derek Crager

What if the biggest training problem inside most companies is not a lack of talent, but the fact that knowledge is trapped in people’s heads and disappears the moment they leave?In this episode of Executive Connect, Melissa Aarskaug sits down with Derek Crager to talk about neurodivergence, voice AI, workforce training, and why the future of learning at work may sound more like a conversation than another slide deck. Derek shares how being diagnosed later in life with autism, ADHD, and dyslexia helped him better understand the way he had always learned, adapted, and built systems. He explains how that perspective shaped his work at Amazon, where he built the company’s highest-rated employee training program, and how it led him to create Pocket Mentor, a voice-based AI tool that helps employees solve real problems in real time.This conversation also explores skilled trades, institutional knowledge loss, employee confidence, human-first AI, and how leaders can turn hard-won expertise into a scalable business after retirement. It is especially useful for executives, operators, training leaders, and anyone trying to preserve critical knowledge before it walks out the door.What You Will LearnHow Derek Crager’s neurodivergence shaped the way he designs trainingWhy a late diagnosis changed how he understood his strengthsWhat made his employee training program at Amazon so effectiveWhy traditional workplace training often fails in real-world environmentsHow Pocket Mentor works as a voice-based AI support systemWhere companies lose money when knowledge is not documentedWhy skilled trades and industrial teams need AI support, not replacementHow to capture tribal knowledge before experts retireWhat human-first AI looks like in workforce developmentHow executives can package their expertise into a scalable business after retirementChapters(0:00) Why Derek’s neurodivergence became a strength in training design(1:23) Derek’s background and the path that led him into workforce learning(3:39) Building Amazon’s highest-rated training program(6:02) The origin story behind Pocket Mentor(12:49) How AI can help close the skills gap and preserve knowledge(17:52) Human-first AI and why the goal is empowerment, not replacement(23:15) How executives can turn experience into a business after retirement(26:31) Derek’s biggest leadership takeaway from Amazon(28:51) Where to learn more about Derek’s books, tools, and workDerek Crager is the founder of Practical AI and the creator of Pocket Mentor, a voice-based AI tool designed to help employees access knowledge and solve problems in real time. With a background spanning blue-collar skilled trades, engineering, talent development, and large-scale workforce training, Derek brings a deeply practical perspective to learning and AI adoption. He is also a neurodivergent leader who uses his lived experience with autism, ADHD, and dyslexia to design systems that support a broader range of minds and working styles.CONNECT with Derek CragerWebsite: https://www.practicalai.app/LinkedIn: https://www.linkedin.com/in/amazonleadership/Grab a copy: https://www.humanfirstai.net/CONNECT with Executive ConnectWebsite: https://www.executiveconnectexperience.comLinkedIn: Melissa AarskaugYouTube: Executive ConnectInstagram: @executiveconnectpodcastTikTok: @executiveconnectpodcastFacebook: Executive Connect