#169: Building Practical AI for Agile Teams with Hunter Hillegas

#169: Building Practical AI for Agile Teams with Hunter Hillegas

Author: Mountain Goat Software December 3, 2025 Duration: 34:14
It’s not just about cool tools. Hunter Hillegas (CTO at Mountain Goat Software) joins Brian to unpack what it’s really like to build with AI—from hallucinations and context management to dev workflows, testing strategies, and where the humans still matter most. Overview This episode dives deep into the real work behind bringing AI into agile. Brian and Hunter trace the arc from early experiments to full-scale agents, sharing what it took to build responsibly on large language models (and what still keeps them up at night). They get into the weeds of context handling, trust and verification, dev productivity, and what makes a good AI coach actually helpful. Along the way, they explore how tools are changing—faster than most teams can keep up—and what that means for the future of learning, coding, and collaborating in agile environments. References and resources mentioned in the show: Hunter Hilligas AI Tool Kit Agile Skils Video Library Mike's Better User Stories Webinar #82: The Intersection of AI and Agile with Emilia Breton #151: What AI Is Really Delivering (and What It’s Not) with Evan Leybourn & Christopher Morales #161: Test-Driven Development in the Age of AI with Clare Sudbery #166: AI Isn’t Coming for Your Job, But It Is Joining Your Team with Dr. Michael Housman Subscribe to the Agile Mentors Podcast Want to get involved? This show is designed for you, and we’d love your input. Enjoyed what you heard today? Please leave a rating and a review. It really helps, and we read every single one. Got an Agile subject you’d like us to discuss or a question that needs an answer? Share your thoughts with us at podcast@mountaingoatsoftware.com This episode’s presenters are: Brian Milner is a Certified Scrum Trainer®, Certified Scrum Professional®, Certified ScrumMaster®, and Certified Scrum Product Owner®, and host of the Agile Mentors Podcast training at Mountain Goat Software. He's passionate about making a difference in people's day-to-day work, influenced by his own experience of transitioning to Scrum and seeing improvements in work/life balance, honesty, respect, and the quality of work. Hunter Hillegas is the Chief Technology Officer at Mountain Goat Software. With over 20 years of experience in software development, product ownership, and team leadership, he leads the creation of tools like the AI Toolkit and Team Home to support effective, engaging learning experiences. Hunter lives in Santa Barbara, California, with his wife and their dog Enzo.

Hosted by Mountain Goat Software, the Agile Mentors Podcast is a conversation for anyone involved in or curious about agile practices. It’s a space where the philosophy meets the practical, moving beyond theory to tackle the real-world challenges teams face every day. You’ll hear discussions that dig into the nuances of Scrum, Kanban, and other frameworks, exploring how they adapt to different environments and scale. The dialogue often focuses on the human side of change-how to foster better collaboration, navigate organizational hurdles, and cultivate a genuinely agile mindset rather than just going through the motions. This podcast serves as a resource for continuous learning, whether you're troubleshooting a specific sprint issue or looking for fresh perspectives to reinvigorate your approach. Each episode aims to provide actionable insights and thoughtful reflection, making the complex landscape of modern software development feel more accessible and manageable. Tune in for honest talk from experienced practitioners who understand that agility is a journey, not a destination.
Author: Language: en-us Episodes: 100

Agile Mentors Podcast from Mountain Goat Software
Podcast Episodes
#186: Why Teams Stop Caring About Retrospectives with Cort Sharp [not-audio_url] [/not-audio_url]

Duration: 32:46
Retrospectives are supposed to help teams improve, but for many teams they slowly become rushed, repetitive, or skipped altogether. In this episode, Brian Milner and Cort Sharp unpack why retrospectives lose their value…
#185: The Real ROI of Agile with Scott Dunn [not-audio_url] [/not-audio_url]

Duration: 41:55
A lot of organizations say they’ve “gone Agile,” but still struggle with missed deadlines, unclear priorities, and teams that feel busy without delivering better outcomes. In this episode, Scott Dunn joins Brian Milner t…
#184: Scrum in High-Stakes Environments with John Holmes [not-audio_url] [/not-audio_url]

Duration: 41:55
Many leaders assume Agile breaks down in highly regulated environments. John Holmes has spent years proving the opposite inside aerospace, defense, and space programs where the cost of failure is extremely high. Overview…
#183: How AI Is Reshaping Product Ownership with Lance Dacy [not-audio_url] [/not-audio_url]

Duration: 33:23
AI can help product owners move faster, but faster is not always better. In this episode, Lance Dacy and Brian Milner explore where AI genuinely improves product work and where teams still need strong judgment, clear pri…
#182: Never Stop Experimenting with Stavros Stavru [not-audio_url] [/not-audio_url]

Duration: 26:59
In a world changing faster than most teams can keep up with, standing still may be the biggest risk of all. Brian Milner sits down with Stavros Stavru to explore why experimentation is no longer optional and how teams ca…
#181: How to Start Agile Without Overengineering It with Cort Sharp [not-audio_url] [/not-audio_url]

Duration: 33:34
Too many teams try to “do Agile” by adding layers of process before they understand the problem they’re trying to solve. In this episode, Brian Milner and Cort Sharp discuss how to start Agile simply, avoid unnecessary c…
#179: Leadership Decisions That Quietly Derail Agile with Mike Cohn [not-audio_url] [/not-audio_url]

Duration: 29:35
Many agile struggles don’t start with the team. They start with leadership decisions that seem reasonable but create friction, confusion, or misalignment over time. In this episode, Mike Cohn outlines the patterns that m…
#178: How AI Is Actually Changing Software Teams with Hunter Hillegas [not-audio_url] [/not-audio_url]

Duration: 29:24
AI isn’t just speeding up coding. It’s starting to change how teams work, what they build, and even who needs to be involved. In this episode, Brian and Hunter separate real impact from hype and explore what’s already sh…
#177: The 5 Habits of High Learning Teams with Lance Dacy [not-audio_url] [/not-audio_url]

Duration: 36:45
Most teams say they want to improve. Few actually build the habits that make it happen. In this episode, Brian and Lance break down what separates teams that learn from teams that stall—and what leaders do that quietly g…