#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
#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…
#176: Why Most Product Organizations Struggle with Jason Knight [not-audio_url] [/not-audio_url]

Duration: 34:42
Many product teams are busy, but not necessarily effective. Brian Milner talks with product consultant Jason Knight about why so many organizations struggle with prioritization, customer insight, and measuring success—an…
#175: When AI Makes Agile Teams Worse with Hunter Hillegas [not-audio_url] [/not-audio_url]

Duration: 27:32
AI can make teams faster. But it can also quietly make them worse. In this episode, Brian Milner and Hunter Hillegas dig into the risks no one wants to talk about—from eroding developer judgment to weakening team communi…
#174: Why Estimating Still Matters with Mike Cohn [not-audio_url] [/not-audio_url]

Duration: 36:14
Estimating can bring out strong reactions, and for good reason. Mike Cohn and Brian Milner unpack why it gets misused, what “estimate responsibly” really means, and how to use planning to make better decisions without tu…
#173: Hiring for Agile Roles That Actually Work with Cort Sharp [not-audio_url] [/not-audio_url]

Duration: 39:28
Hiring for Scrum roles is harder than it looks. Making the wrong call can derail an Agile transformation before it even starts. In this episode, Brian and Cort unpack what to actually look for in Scrum Masters, Product O…
#172: The Five Pillars of Agile Transformation with Mike Cohn [not-audio_url] [/not-audio_url]

Duration: 32:30
Most agile transformations start with energy, and then stall out when things get complex. In this episode, Mike Cohn returns with a practical framework to help teams and leaders spot what’s missing, build lasting momentu…
#171: Why Agile Teams Succeed—or Don’t with Colin Fisher [not-audio_url] [/not-audio_url]

Duration: 34:02
Most teams aren’t broken because of individual incompetence. They’re struggling because the group itself isn’t set up to thrive. In this episode, author and researcher Colin Fisher joins Brian to reframe how we think abo…
#170: Leadership Lessons from the Marine Corps with Tanner Wortham [not-audio_url] [/not-audio_url]

Duration: 30:11
What can Agile leaders learn from the Marines? In this episode, Tanner Wortham joins Brian to share how principles of military leadership—like building authority into the trenches, experimenting under pressure, and prior…