#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: 50

Agile Mentors Podcast from Mountain Goat Software
Podcast Episodes
#165: Can Your Product Process Keep Up With AI with Cort Sharp [not-audio_url] [/not-audio_url]

Duration: 37:09
If AI is speeding up how fast we can ship, what’s slowing teams down now? Brian and returning guest Cort Sharp dig into the emerging friction between AI-assisted development and the still-slow art of product decision-mak…
#164: Why Innovation Efforts Fall Flat with Tendayi Viki [not-audio_url] [/not-audio_url]

Duration: 34:23
Tendayi Viki joins Brian to unpack the difference between doing innovation and delivering value, with practical takeaways for product folks, innovation teams, and anyone who wants to stop spinning their wheels. Overview…
#163: Should We Go Back to the Office? It Depends. with Lance Dacy [not-audio_url] [/not-audio_url]

Duration: 42:07
Five years post-COVID, are we any closer to knowing what kind of work environment actually works best? Brian and Lance dig into the real drivers behind return-to-office mandates, remote productivity myths, and why "conte…
#161: Test-Driven Development in the Age of AI with Clare Sudbery [not-audio_url] [/not-audio_url]

Duration: 41:05
AI might write your code, but can you trust it to do it well? Clare Sudbery says: not without a safety net. In this episode, she explains how test-driven development is evolving in the age of AI, and why developers need…
#160: The Real Work of a Scrum Master with Brian Campbell [not-audio_url] [/not-audio_url]

Duration: 34:03
What separates a solid Scrum Master from a great one? In this episode, Brian Milner sits down with veteran Scrum Master Brian Campbell to talk about the balance between being empathetic, staying grounded, and knowing whe…
#159:  Is Scrum Really Too Many Meetings? with Lance Dacy [not-audio_url] [/not-audio_url]

Duration: 43:09
“Too many meetings” is one of the most common complaints in Scrum teams, but is it really the meetings, or what’s (not) happening in them? In this episode, Brian and Lance Dacy dig into the events of Scrum to uncover wha…
#158: Should You Skip the Sprint Retrospective? with Mike Cohn [not-audio_url] [/not-audio_url]

Duration: 29:18
Is your team dreading retrospectives, or skipping them altogether? Mike Cohn joins Brian Milner to unpack what’s really going wrong (and how to fix it) so retros don’t just take up time… they actually make your team bett…
#157: What Teams Are Struggling With Right Now with Cort Sharp [not-audio_url] [/not-audio_url]

Duration: 39:27
Scrum isn’t new, but the questions teams are asking about it are evolving. In this episode, Brian and Cort Sharp compare notes on what they're hearing in class, in the community, and behind the scenes. Overview In this e…