Derek Crager, Practical AI: How to Keep Your Best Employee Forever

Dec 3, 2025

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In this episode of Collisions YYC, Tyler is joined by Derek Crager, Founder of Practical AI, the mind behind Practical AI and creator of Pocket Mentor, an AI-powered voice companion that delivers scalable, personalized coaching for real-world leadership challenges. Drawing from his deep experience in the tech space, including his time at Amazon, Derek shares how simplicity, empathy, and human-centred design inform his approach to AI development. The conversation explores how Pocket Mentor bridges the gap between formal training and everyday problem-solving, offering just-in-time guidance in moments that matter from onboarding and performance feedback to high-stakes leadership decisions. Derek also discusses the ethical responsibilities of building AI tools, especially those that influence how people lead, manage, and grow in their roles. If you're curious about how AI can enhance human capability in the workplace, this episode is a must-listen.

In this episode:

How Pocket Mentor turns everyday work into scalable, accessible training
Why the AI panic (job losses, sentience fears) needs a serious reality check
What Amazon taught Derek about simplicity and user experience
Why neurodiversity and AI might be the perfect match
How storytelling and voice interfaces are shaping the next era of learning

Top 3 Wisdom Bombs

"We use AI not to think for the person, but to think with the person, just like a true mentor would.” - Derek Crager

“The best interface a human has is another human. And that can be a true human or it could be AI with the voice of a human acting as a proxy.” - Derek Crager

“AI is a tool and we can use it, you know, for humanity or against humanity...we are at a dividing point right now. We are at a fork in the road.” - Derek Crager

This episode is brought to you by clearmotive marketing. When it comes to marketing that truly matters to your business, clearmotive is your go-to partner. With a proven track record of more than 15 years, they understand what makes your business tick. Learn more at https://www.clearmotive.ca and discover how clearmotive can help your marketing thrive.

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Host links:

Tyler’s website: https://www.tylerchisholm.com

Tyler’s LinkedIn: https://www.linkedin.com/in/tylerchisholm

Guest links:

Derek Crager’s LinkedIn: https://www.linkedin.com/in/amazonleadership

Practical AI’s Website: https://www.practicalai.app

Practical AI’s LinkedIn: https://www.linkedin.com/company/practical-ai-for-business

Collisions YYC is a Tyler Chisholm original production // Brought to you by clearmotive marketing