#186: Why Teams Stop Caring About Retrospectives with Cort Sharp

#186: Why Teams Stop Caring About Retrospectives with Cort Sharp

Author: Mountain Goat Software May 27, 2026 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 and what Scrum Masters and leaders can do to make them useful again.   Overview When a team stops engaging in retrospectives, it is usually a symptom of something deeper. Sometimes the format has become stale. Sometimes the team no longer feels safe being honest. And sometimes the biggest issue is that retrospectives create plenty of discussion but very little meaningful change. In this conversation, Brian and Cort explore the most common reasons retrospectives begin to fail and how teams can rebuild trust in the process. They discuss the importance of psychological safety, why teams should focus on fewer actions instead of trying to fix everything at once, and how Scrum Masters can better tailor retrospectives to the personalities and working styles of their teams. They also share practical ideas for making retrospectives more engaging, more actionable, and more valuable over time.   References and resources mentioned in the show: Cort SharpAmy Edmonson, Psychological Safety#139: The Retrospective Reset with Cort Sharp#141: Cooking Up a Killer Retrospective with Brian MilnerThe Empirical Retrospective Approach by Mike CohnSubscribe 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 the Scrum Master of the producing team and the Agile Mentors Community Manager. In addition to his love for Agile, Cort is also a serious swimmer and has been coaching swimmers for five years.

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
#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…
#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…