#139: The Retrospective Reset with Cort Sharp

#139: The Retrospective Reset with Cort Sharp

Author: Mountain Goat Software March 26, 2025 Duration: 39:33
Retrospectives shouldn’t suck the energy out of your team—or get skipped entirely. In this episode, Brian and Cort share how to fix the most common retro fails and announce two brand-new tools to help you run retros that actually work. Overview In this episode of the Agile Mentors Podcast, Brian Milner and Cort Sharp break down why retrospectives are more than just a “Scrum box to check.” They’re the powerhouse behind continuous team improvement. From battling retro fatigue and quiet-room energy to creating psychologically safe environments and tying retrospectives to real results, they cover it all. Plus, Brian reveals the launch of two new on-demand courses—Better Retrospectives and The Retrospectives Repair Guide—designed to help teams stop skipping and start optimizing their retros. Whether you're a Scrum Master, coach, or facilitator, this episode is your practical guide to making retrospectives worth everyone’s time again. References and resources mentioned in the show: Cort Sharp Blog: Retrospectives With a Quiet Team Blog: Does a Scrum Team Need a Retrospective Every Sprint Mike Cohn’s Better User Stories Course Scrum Repair Guide 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 SVP of coaching and 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. Auto-generated Transcript: Brian Milner (00:00) Welcome in Agile Mentors. Welcome back for another episode of Agile Mentors podcast. I'm with you as always, Brian Milner, but today we're gonna have a continuation of something we tried, a little experiment we tried a few weeks back here. I've got Mr. Court Sharp back with us. Welcome back in court. Cort Sharp (00:18) Hey, Brian, thanks for having me on again. I had lot of fun last time I was on here and it was a great discussion. So thanks for bringing me back. Brian Milner (00:21) Yeah. Yeah, it's, oh, absolutely. Yeah, know, got a lot of people said, hey, we kind of like that court guy. Kind of like hearing from court. So we wanted to have court back, you know, because you guys told us that you liked him. And we also wanted to have him back because we just thought this format kind of worked for various reasons. And last time we kind of hit on some things that were kind of more hot button issues of the day. things that have been flowing through social media or other things around Agile. But we wanted to have a little bit more of a focus for today's episode. And we're going to focus really on the topic of retrospectives. And maybe make a little announcement here along the way as we go along. But we're actually going to switch roles here a little bit. I'm going to kind of pass the ball over to Court. And I'm going let Court drive this, just like he did in the last episode. Ball's in your court. Ha ha, get it? Cort Sharp (01:18) Ha ha, court, there you go. Well thanks, Brian. Once again, I love coming on here, I love chatting with you. And like you said, yeah, we're gonna be talking about retrospectives today, mostly because I have been struggling with answering questions about retrospectives. I think this is one of the more common meetings within Scrum that just gets skipped over, just people don't find value in it. Brian

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
#186: Why Teams Stop Caring About Retrospectives with Cort Sharp [not-audio_url] [/not-audio_url]

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…
#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…