Agile Mentors Podcast from Mountain Goat Software

#175: When AI Makes Agile Teams Worse with Hunter Hillegas

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 communication—and what healthy teams should do about it.
 
Overview
AI tools are powerful. They can generate code, draft tests, and accelerate delivery in ways that felt impossible just a few years ago. But speed is not the same as effectiveness.
In this episode, Brian sits down with Mountain Goat Software CTO Hunter Hillegas to explore where AI may actually be hurting Agile teams. They discuss the risk of losing junior developer growth paths, the illusion of productivity through inflated metrics, the danger of outsourcing judgment, and how AI can quietly create communication silos inside Scrum teams.
This is not an anti-AI conversation. It is a practical one. You will hear what guardrails healthy teams should consider, why accountability still belongs to humans, and how to use AI as a tool without letting it reshape your culture in ways you did not intend.
If your team is leaning into AI, this episode will help you do it with your eyes open.
 
References and resources mentioned in the show:
Hunter Hillegas
Blog: AI Doesn’t Eliminate Agile Teams — It Increases the Need for Great Ones by Mike Cohn#169: Building Practical AI for Agile Teams with Hunter Hillegas
#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 MoralesMountain Goat Software
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  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.

#174: Why Estimating Still Matters with Mike Cohn

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 turning numbers into weapons.
Overview
In this episode, Brian sits down with Mike Cohn to talk about estimating and planning in a way that teams can actually live with. They explore why estimates became such a hot button topic, what the “no estimates” movement is reacting to, and how Mike’s thinking has evolved over time. You will hear practical guidance on story points versus time, why teams should estimate only when it helps someone make a decision, and how to keep estimates from damaging trust. They also cover where flow metrics help, where they fall short, and how teams build credibility with leadership through responsible planning.
References and resources mentioned in the show:
Mike Cohn
Estimating & Planning in Agile - A 2026 Field Guide
Accurate Agile Planning Course
Blog: Estimating and Planning in Agile: Why They Still Matter in 2026 by Mike Cohn
Blog: Getting Better Estimates Is Easier Than You Think by Mike Cohn
Blog: What Are Agile Story Points? By Mike Cohn
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.
Mike Cohn, CEO of Mountain Goat Software, is a passionate advocate for agile methodologies. Co-founder of Agile Alliance and Scrum Alliance, he thrives on helping companies succeed with Agile and witnessing its transformative impact on individuals' careers. Mike resides in Northern Idaho with his family, two Havanese dogs, and an impressive hot sauce collection.

#173: Hiring for Agile Roles That Actually Work with Cort Sharp

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 Owners, and Developers—beyond the job title and shiny certifications.
Overview
What makes someone a great Scrum Master? How do you spot the difference between a capable Product Owner and a glorified backlog manager? And what qualities matter most in a developer on a cross-functional Agile team?
In this episode, Brian Milner and Cort Sharp dig into one of the most foundational (and overlooked) parts of successful Agile adoption: hiring. You’ll learn what to include—and what to avoid—in your job descriptions, how to interview for the “real” skills that matter, and why collaboration often matters more than technical brilliance. Whether you're filling new roles or leveling up existing ones, this conversation will help you build stronger, more resilient teams from day one.
References and resources mentioned in the show:
Cort Sharp
Blog: 7 Questions to Determine if Being a Scrum Master Is Right for You by Mike Cohn
#155: Preparing for Interviews the Agile Way with Tali Shlafer
#157: What Teams Are Struggling With Right Now with Cort Sharp
Agile Skills Video Library
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.
Cort Sharp is an Agile Coach, Trainer, and Scrum Master. In addition to his love for Agile, Cort is also a serious swimmer and has been coaching swimmers for five years.

#172: The Five Pillars of Agile Transformation with Mike Cohn

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 momentum, and navigate change with more clarity and intention.
Overview
Agile isn’t just a set of practices—it’s a mindset shift, a role shift, and a culture shift. And without the right support, even the best-intentioned transformation efforts can lose steam. In this episode, Mike Cohn joins Brian to walk through his Five Pillars of Agile Transformation—a practical structure for guiding change that actually sticks.
Whether you're leading a single team or rolling out agile across the organization, this conversation will help you focus your efforts, spot common gaps, and use agile principles to strengthen your transformation from the inside out.
References and resources mentioned in the show:
Mike Cohn
What Happens When One of the Pillars is Missing Graphic
The Five Pillars of a Successful Agile Transformation by Mike Cohn
#102: Communicating Agile Transformations with McCaul Baggett
#110: Overcoming Organizational Dysfunctions with Lucy O’Keefe
#152: The Five Pillars of Real Agile Improvement with Mike Cohn
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.
Mike Cohn, CEO of Mountain Goat Software, is a passionate advocate for agile methodologies. Co-founder of Agile Alliance and Scrum Alliance, he thrives on helping companies succeed with Agile and witnessing its transformative impact on individuals' careers. Mike resides in Northern Idaho with his family, two Havanese dogs, and an impressive hot sauce collection.

#171: Why Agile Teams Succeed—or Don’t with Colin Fisher

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 about team performance, conflict, and psychological safety through the lens of real science, real practice, and a little jazz.
Overview
Group dynamics aren’t fluff. They’re the operating system behind every Agile team’s success (or struggle). Colin Fisher, author of The Collective Edge, joins Brian to share what decades of research and hands-on observation reveal about high-performing teams. From ideal team size (spoiler: it’s 4.5), to avoiding the trap of blaming individuals for systemic issues, Colin offers a practical, thought-provoking look at how to build more resilient, collaborative, and human-centered teams.
Expect fresh insights on team launch moments, role clarity, feedback culture, remote collaboration and how to keep your team “groupy” in the best possible way.
References and resources mentioned in the show:
Colin Fisher
Collective Edge by Colin Fisher
Colin's Free Newsletter
LinkedIn
YouTube
#80: From Struggling to Success: Reviving Agile Teams with Mike Cohn
#143: What Still Makes Teams Work (and Win) with Jim York
Self-Organizing Teams Are Not Put Together Randomly by Mike Cohn
Agile Skills Video Library
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.
Colin Fisher is a former professional jazz musician turned organizational behavior expert who now helps teams unlock their creative and collaborative edge. A professor at University College London and author of The Collective Edge, Colin draws on decades of research—and a bit of jazz improv—to help leaders understand what really makes groups tick.

#170: Leadership Lessons from the Marine Corps with Tanner Wortham

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 prioritizing shared mission over ego—map surprisingly well to modern Agile teams.
Overview
In this conversation, Brian sits down with Marine Corps veteran and Execution Architect Tanner Wortham to explore the parallels between leading Marines and leading Agile teams. Drawing from both military and coaching experience, Tanner unpacks how the Corps’ “rule of three,” mission-first mentality, and obsession with experimentation mirror the best of Agile thinking.
They discuss how effective leadership empowers decision-making at the edges, why conflict shouldn't be avoided but navigated with curiosity, and how facing toward hard problems—rather than away from them—builds high-performing, resilient teams. Whether you're coaching a Scrum team or leading large-scale transformations, Tanner’s insights offer a fresh lens on what it really means to lead with agility.
References and resources mentioned in the show:
Tanner Wortham
What the Corps Calls Leading Marines Others Call Agility
#113: Influence Without Authority with Christopher DiBella
#135: Leading Without Authority with Pete Behrens
#132: Can Nice Guys Finish First? with Scott Dunn
Get the Agile Skills Video Library Use code PODCASTSKILLS for $10 off
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.
Tanner Wortham is a former Marine turned leadership coach who helps teams and execs cut through the noise, lead with clarity, and actually get things done. With experience at LinkedIn, Salesforce, and beyond, he brings a no-fluff, human-first approach to growth, agility, and real leadership.

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

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.

#168: Gratitude, Growth, and the Power to Evolve with Brian Milner

It’s not a full episode this week—but it might be the one your heart needs. Brian Milner shares what he’s truly grateful for this year (spoiler: it’s not a new tool or framework), reflects on the human side of agility, and invites you to join him in a quick pause before the final sprint of 2025.
Overview
In this special solo episode, Brian Milner pauses to reflect on what he's most grateful for this year—and invites you to do the same. From a renewed focus on the human side of agility to the evolving nature of our roles as leaders and practitioners, this heartfelt message is a reminder that change isn’t just necessary—it’s powerful. Brian also shares his appreciation for the Mountain Goat Software team and a behind-the-scenes shoutout to Agile Mentors’ own Laura Kendrick for making the show possible. Short, sweet, and soul-centered, it’s a moment to breathe, acknowledge growth, and say thanks before we sprint toward the end of the year.
References and resources mentioned in the show:
Five Lessons I’m Thankful I Learned in my Agile Career by Mike Cohn
#123: Unlocking Team Intelligence with Linda Rising
#125: Embracing Gratitude in Challenging Times with Brian Milner
#134: How Leaders Can Reduce Burnout and Boost Performance with Marcus Lagré
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.

#167: Running Better Remote Meetings with Evan Unger

Consultant and collaboration expert Evan Unger joins Brian to share practical tactics for leading more engaging, effective meetings that actually get results (and don’t drain everyone’s will to live).
Overview
In this episode of the Agile Mentors Podcast, Brian Milner welcomes longtime consultant and facilitation expert Evan Unger to dig into one of the most persistent workplace headaches: remote meetings.
With decades of experience helping leaders shift from “presenting at” to true collaboration, Evan shares how a simple POPRA framework can change the game, why simultaneous chat might be your new secret weapon, and what leaders get wrong when they step into the (virtual) room. From deprogramming the HIPPO effect to humanizing remote collaboration, this conversation is packed with real talk, useful tools, and just enough snark to make you want to fire up your next Zoom meeting with purpose.
References and resources mentioned in the show:
Evan Unger
Collaborative Leadership: A Virtual Immersion™ Program
#138: The Bad Meeting Hangover with Julie Chickering
#142: Communication Patterns Keeping Your Team Stuck with Marsha Acker
Agile Skills Video Library Use code PODCASTSKILLS for $10 off
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.
Evan Unger is a collaboration expert and consultant who’s spent over three decades helping leaders turn messy meetings into meaningful progress—even in a post-pandemic, Zoom-fatigued world. As managing partner at Schwartz + Associates, he now trains leaders in the art of virtual facilitation and high-stakes collaboration, so teams can stop surviving meetings and start making decisions that actually stick.

#166: AI Isn’t Coming for Your Job, But It Is Joining Your Team with Dr. Michael Housman

AI is already changing how we work—and how we work together. In this episode, Dr. Michael Housman joins Brian Milner to explore how AI is reshaping team collaboration, decision-making, and the very structure of Agile teams.
Overview
We keep talking about AI like it’s something that’s coming. But as Dr. Michael Housman points out, it’s already here—embedded in our tools, shaping how we collaborate, and quietly shifting the makeup of our teams.
In this episode, Brian sits down with Dr. Housman, CTO, keynote speaker, and author of the upcoming Future Proof: Transform Your Business with AI or Get Left Behind, to talk about what AI is already doing in Agile environments. From how it’s helping Scrum Masters level up decision-making to how it might literally join your org chart, they dig into what’s helpful, what’s hype, and what leaders need to pay attention to right now.
References and resources mentioned in the show:
Dr. Michael Housman
#82: The Intersection of AI and Agile with Emilia Breton
#99: AI & Agile Learning with Hunter Hillegas
#151: What AI Is Really Delivering (and What It’s Not) with Evan Leybourn & Christopher Morales
#165: Can Your Product Process Keep Up With AI with Cort Sharp
Agile Skills Library use code PODCASTSKILLS for $10 off
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.
Dr. Michael Housman is the author of Future Proof: Transform Your Business with AI (or Get Left Behind) and the founder and CEO of AI-ccelerator where he helps organizations leverage advances in artificial intelligence. He is a seasoned technologist with over 15 years of experience architecting AI platforms in sectors ranging from hiring and fraud detection to customer communication and real estate lending. His research has been published in a variety of peer-reviewed journals and profiled by such media outlets as The New York Times, Wall Street Journal, The Economist, and The Atlantic. Dr. Housman received his A.M. and Ph.D. in Applied Economics and Managerial Science from The Wharton School of the University of Pennsylvania and his A.B. from Harvard University.