Agile Mentors Podcast from Mountain Goat Software

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

Dec 3, 2025

Hunter Hillegas, CTO at Mountain Goat Software with 20+ years building developer tools, outlines building the Agile AI Toolkit. He discusses coaching assistants, story splitting and backlog generation. They cover handling hallucinations, context management, testing and integrating agents with real data. The conversation highlights how AI changes dev workflows while keeping humans in the loop.

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ADVICE

Use AI To Augment Agile Roles

Use an AI coach to augment agile roles rather than replace them.
Hunter built the Agile AI Toolkit with conversational coaching, story-splitting mode, and backlog generation to save time and teach best practices.

INSIGHT

Quality Control Is The Primary AI Challenge

Controlling output quality is the core challenge when building work-focused AI tools.
Hunter worried about hallucinations and bad or off-topic responses, and added mitigations plus user feedback during beta tuning.

ANECDOTE

Beta Tuning Fixed A Peloponnesian War Tangent

Early goat bot experiments sometimes produced bizarre outputs like a lengthy Peloponnesian War tirade.
Hunter recounted beta tuning to prevent off-topic or inappropriate responses for a professional coaching tool.

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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
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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.