Revitalizing Retrospectives: Embracing Creativity and Structure

Tired of “What went well?” and “What didn’t”? Brian Milner is here to help you cook up retrospectives that actually get your team thinking, collaborating, and improving. From creative themes to actionable frameworks, this is your behind-the-scenes guide to better retros.

Overview

Do your retrospectives feel more “check-the-box” than game-changing? Brian Milner shares his full recipe for planning and facilitating retrospectives that actually matter.

Whether your team is stuck in repetition, tuning out, or phoning it in, Brian’s step-by-step approach will show you how to bring structure, creativity, and energy back into the room.

Brian walks you through the five essential components of a retrospective, including how to match formats to your team’s personality, align activities with Agile's three pillars (transparency, inspection, and adaptation), and spark meaningful change with every session.

References and resources mentioned in the show:

Stranger Things Retrospective Download
Agile Retrospectives by Esther Derby & Diana Larsen
Retromat
Blog: Overcoming Four Common Problems with Retrospectives by Mike Cohn
Blog: Does a Scrum Team Need a Retrospective Every Sprint? By Mike Cohn
#139 The Retrospective Reset with Cort Sharp
Retrospectives Repair Guide
Better Retrospectives
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.

Auto-generated Transcript:

Brian Milner (00:00)
Welcome in Agile Mentors. We are back for another episode of the Agile Mentors podcast, like we always do. And I'm with you as always, Brian Milner. Today we have with us, me, just me. Now, before you get frustrated with that or think we're copping out in some way, this is intentional. I wanted to have an episode to myself because and working through all this stuff around retrospectives, I thought that it might be good to take an episode here. And I kind of thought of it sort of like a cooking episode, right?

Like if you watch a cooking show, you know, Gordon Ramsay show or something, they'll walk you through how they make something. And it's from start to finish. They show you the ingredients. They show you how everything's put together. And then you see this beautiful dish at the end. Well, I've often compared the way that you can format a retrospective to a little bit like a meal, because a meal has different courses in it. And a retrospective should have these themed areas or repeatable sections of it. And so I thought of it a little bit like making a meal.

So I thought I'd just walk you through a little bit step by step. what I'm thinking here and how I would go about doing it. this is, you know, we're cooking up something special here. It's a kind of a recipe here that's, you know, equal parts creative and effective. It's a way to try to keep your retrospectives interesting, but also keep them to be solid and where you can have an actual outcome that comes from this.

And you actually make definitive changes here with your team as a result. So there's a couple of retrospective courses that I have coming out where I go into detail about all these things, but I wanted to take an episode where I could walk you through and just have you kind of peer over my shoulder a little bit about how I might do this if I was going to create a retrospective for a team.

So first starters, I think we have to understand that there is a menu to follow, right? And I kind of use this menu metaphor because one of the great things about when you go out and you have a meal at a nice restaurant is there's a repeatable pattern to it. You kind of expect that they're gonna bring you a drink first and then maybe you have, if it's a really fancy restaurant, maybe you have appetizers first or hors d'oeuvres even before appetizers, then you maybe have appetizers or not. Then you have a main course and maybe you have a salad even before the main course and then you have a a meal, and then you have some kind of a dessert afterwards, maybe even some kind of a cocktail at the end of the meal or coffee at the end of the meal.

But there's sort of a pattern to it. And regardless of what restaurant you go to, you kind of repeat that same pattern. Now, I know that there's times you'll be, this is where the metaphor kind of breaks down a little bit, I get it. You may not have the same pieces every time. And what we're going to be talking about here as a retrospective pattern is that, yes, you should sort of follow the same pattern.

You can't really get to, let's say, dessert. You can't just skip and go to dessert, right? You've got to go through this journey of the other sections so that you can end up at dessert and really fully appreciate it, right, and get the most out of it.

So that's where this metaphor is a little bit of a, starts to break down a little tiny bit. But. I want to talk about here first why retrospectives matter and why they often go stale. I think they often go stale for a lot of reasons, but one of the chief reasons I've encountered when I work with teams is that the Scrum Master on the team really only has a small amount of formats and styles that they have to work with. They have a small little set in their toolbox. And they may even rotate through a few of them. But at the end of the day, it's kind of a small toolbox. There's only a few tools in there. And if I'm a team, if I'm a member of that team, you can imagine how I might get bored.

And I might think this is not really worthwhile if I'm showing up every single time and I'm hearing the same exact questions. What did I do? What do we do well? What do we not do so well? Do I have any roadblocks? If I'm just asked that same thing every time, then I might not feel like this is a very worthwhile thing. Or I might get to the point where I feel like, gosh, I've answered the same question, you know, three sprints in a row. I just, got nothing more for you Scrum Master. I just, I can't dig any deeper.

I've given you everything and it just feels like this is the, you know, groundhog day. We're doing the same thing over and over again, but nothing's really changing. So. I think it's important that we be able to switch things up, but it's not change just for change sake. That's why I think that having a structure of some kind can give you that pattern to fall back on that can make it effective, but then also can provide variety, can make it something that changes over time as you do this with your team. Doesn't mean that you can't ever repeat a format that you've used. I don't think that's a bad thing.

I just wouldn't want to repeat the same, just handful, small little number of them over and over again. That's going to get repetitive and it's going to make people a little frustrated. The other thing is I think you have to match these to the personality of your team. Your team might be more outgoing or they might be more introverted. You might have people who prefer activities or little more, you know, kind of quiet activities or some that are more verbal, you know, require more discussion. That's really an individual thing for your team.

So I think you have to think as you go through this, what's going to work for these people, right? For this set of individuals that I am working with. You know, I always say there's kind of a first commandment for Scrum Masters, know thy team. And I think that's really something that's important for us to grasp onto is we have to know our team. can't coach to the average.

Right? We have to coach to the individual, to what we have on our team, because your team is unique. That set of individuals has never come together anywhere else in the world. Right? Those personalities. And what you want is to find out how to make that set of people work well together. Right? How do they work best together? Not how does every other team in the world work best or how does the average team work best? How does your team work best? Right? So with all of this is sort of setting this and saying that there should be a pattern.

I do want to give the hat tip here and say that the Esther Derby Dinah Larson book on retrospectives is one I strongly recommend. In fact, pretty much my whole career as a trainer, I have said, when people say if there's one book, if I'm to be a Scrum Master, if there's one book that you would say would be really impactful to me from pretty much day one, I have pointed to that book. It's called Agile Retrospectives, Esther Derby, Dinah Larson. And in that book, they lay out a pattern of kind of five phases that go through it.

I'm going to distill it down because to me, it's sort of the three middle ones that are the most important. I will talk about the two on the ends here as well and kind of put that on top of these three. But sometimes I find people find it easier if they just remember what I'm gonna teach you here about the three that are in the middle. So in Scrum Master classes, we will talk often about how there's these three pillars of the Agile process or three pillars of empiricism. Empiricism says that we learn through experience. Well, I always say in class, it's not enough to just do the wrong thing over and over again. I gain a lot of experience by doing the wrong thing over and over, but I don't learn from it.

And the three pillars are what's needed to make sure you learn from them. And I'm sure you've heard these before, but if you haven't, transparency, inspection, adaptation. Those are the three. Transparency meaning we're not going to be clouded about how we do the work. We're going to be very transparent, open about it. We're going to try to reveal how we work best as much as possible. Inspection, that we're going to actually take time and pause and try to figure out not just what happened, that would be transparency, right?

What's the reality of what just happened? But inspecting says, why did this happen? Right? What's the root cause of it? I don't want to just deal with the symptoms, right? If we just try to cure the symptoms over and over again, we still have the same disease, we still have the same illness, and we're not really getting to the root cause.

So inspection says, we're going to take time out to actually get to the root cause. And then adaptation, the last one, is probably the most important step here, because if you figure out what's wrong, but you don't ever do anything about it, well, we're doomed to have the same exact discussion again. So adaptation says, now that you know what the problem is, what are you going to try different? We may not even know exactly what the right thing to do is, but we got to try something. What we know for certain is what we did didn't work.

That's the one thing we absolutely can't do again, is exactly what we did. We've got to try something new so that we move on, right? So that we find out more information and get closer to whatever our final solution is. So transparency, inspection, adaptation, those three actually serve as a good guideline or three phases you can think about for your retrospectives.

There needs to be a transparency phase where you try to figure out what happened this last sprint. there needs to be an inspection phase where now that we know what happened, we got to ask the question, why did it happen? And we need to get to the root cause of why it happened. Now that we know what that is, then we have to move on to adaptation to say, what are we going to do about it? How are we going to take this knowledge we just gained and actually make a change? So we need activities around all three.

And what I'm saying here to you is that can serve as your menu. I can do lots of different activities that would match these three areas. Now, I do, again, want to go back to the Esther Derby, Dinah Larson book, because their five phases adds one on the beginning, one on the end, which I actually do think are very helpful. The first one is kind of opening the retrospective. It's a way of trying to just start to get voices in the room. And this is something I will often do as well. Just a quick, quick exercise to just get people to start talking.

And that's one of the ways you can start to get a quieter group to get involved is throw them something really easy to respond to right out of the gate. And then the last one is to close the retrospective. Closing the retrospective is a great way to then try to sum it all up and say, well, here's the takeaways, here's the things we're going to do about it, and we're going to move forward from here.

Opening the retrospective to that introduction can also then review what you talked about at the end of the last. retrospective. You can say, here are the things that we decided, and let's talk about what's been done about them before you start to inspect the current retrospective. So given that, right, I know I'm going fast here, but you can rewind and listen back to this if you need to.

But if you think about that, that you have these kind of phased approaches, and think of it like a menu, right? There's different courses to my menu. Well, I'm not going to serve the same meal every time. That would be boring. So I got to find out different things I can serve for each course of my retrospective. Now, here's where it gets interesting, right?

Because there are lots of tools out there. And there's a website that I often recommend called RetroMAT. RetroMAT is a great site where you can go to, and it has those five phases. You can kind of scroll through different exercises for each of the five phases. they sort of have, you you can kind of mix and match and create your own menu based off of that.

And doing that is absolutely free. Now they have paid things there as well. They're not a sponsor. I don't get any kickbacks or anything from them. But they have some paid activities as well as far as having things like Mural and Miro templates that you can use if you want to do that as well. So there's lots of things you can do there to thank them for what they put together. But there are times when Maybe you're trying to fit this to your team specifically, or you've grown tired of the exercises that you're used to, and you want to find some new dynamic to add into your retrospective.

So what I'm going to do is kind of walk you through what I would do if I wanted to take some kind of a theme and create a new retrospective that's themed around a certain topic. Now I will say that this theme is gonna go just in one of our sections. So it's not going to go throughout it. I'm not gonna be that creative here with you on it, because I don't think you need to be. I don't think you need to have this, it's not like a theme to party, right? You can just take the theme and use it in one of the sections. So what would I do for something like this?

Well, I'd start with, as I said, some way to kind of open the retrospective. And I like to have little quick activities as I said, that just get voices in the room. an example of things I've done in the past. Ask the team a quick question like, if this last sprint were a song title, what song title would you use to describe this last sprint? And people can use whatever kind of music they like, right? It doesn't matter.

They can just call it any songs that they're familiar with. Or do movie titles. I've had a lot of fun in the past doing that with teams where I'll say, hey, shout out a movie title that might represent this last sprint. You just want to find something quick that people can shout out like one or two word answers, right? Or a small sentence in the case of a song title or movie title or something like that.

But something that they can tie it into, right? And it doesn't have to be anything that makes perfect sense, right? It can be kind of crazy. It can be... You know, if this last sprint were a flavor of Starburst or, you know, an color, what color would it be and why? And just have people, you know, shout out whatever they think the answer would be.

They might have to be a little creative with their answers when they do that. But that's okay. You're just giving them an opportunity to have a few voices start to enter the conversation. Don't force anyone, right? Don't force anyone to shout out, but give them an opportunity to. So I'm going to open the retrospective with some kind of fun, quick exercise like that.

Probably won't take more than five minutes, okay? Then I want to move into that transparency section. And the way I frame transparency is what actually happened this last sprint?

What was the reality of what happened this last sprint? So here's where I'm going to inject a themed kind of approach. And I just, I go through a couple of examples in our courses where I talk about doing this, but I picked a different one here for this podcast episode that I've put together right before this recording to try to walk you through a little bit of how I did this.

So I tried to pick something that was a little more relevant to today. I know that this is popular and people are looking forward to the next season, which is about to come out. sometime soon, I know they've been shooting it, but I picked the theme, Stranger Things. And I just thought, what if my team, you know, had, I knew there were some people on my team really into Stranger Things, or what if I just knew they were aware of it, they knew what it was, and I wanted to have a theme built around this.

So here's how easy it is to do this. I went to chat GPT, and I asked it to give me some, you know, putting together a retrospective that I want to theme it around stranger things. And give me some major themes from Stranger Things that might align to Some different ways of collecting information around what actually happened this last sprint. And. They gave me a long list of different things.

And I read through these and kind of tweaked them, talked back and forth with it a little bit, kind of refined. And I distilled it down to five sort of themes or categories I thought would be fun and would kind of challenge the group to think along different lines of thought. So here's what I came up with with Chat GPT's help. My first category. I called running up that hill.

And what I put for the prompt for this one is what felt like an uphill battle this sprint? Now just think about that, right? In traditional sprints, there's lots of things that are just, I'm essentially asking what was the obstacles?

What were the hurdles in this sprint? But I'm getting them to think about it in little different way by saying, what was an uphill battle in this sprint? And even that subtle rewording, of that prompt can trigger people's brains to work in a different way and get them to think along different lines. If I just ask over and over again, you know, what was a blocker of this sprint or what blockers do we encounter this sprint? If I use those same words over and over, I get sort of immunized against them and I can't really think about anything new.

But just phrasing it that little slightly different way, what felt like an uphill battle this sprint I think can really trigger some new ways of thinking. So that was my first category. The second one that I came up with, big theme here in Stranger Things, was the upside down. And I related it this way to say, what is completely upside down right now?

What is the opposite of what it should be right now? Now here, I'm trying to get them to think about things that are not really going well, right? Things that are going the opposite direction that they should, and it's upside down from what should be the normal. Right? And again, we're just thinking along this theme of stranger things and I'm tricking their brains a little bit into thinking along a different line, right? To examine it from a different point of view. My third category that I thought would be fun was I titled Vecna's Curse.

And what I prompted here for this one was what haunted the team this sprint or kept coming back up to bite us. And The idea here is to get them to think about things that were maybe decisions we wish we had made differently. These could have been decisions in the past. It didn't have to be a decision from this sprint. But what are those things that we felt kind of like was like Vecna's curse?

It was just something that kept rearing its ugly head. And it was just a struggle for us to get around. My fourth one, just to have a little fun. I call the fourth one Surfer Boy Pizza. And what I put as a prompt on this one was, where did we bring the chill? Where did we bring the creative spin to a tough solution during the sprint? So here I'm wanting to celebrate good things, right?

And I'm asking that in a funny way. So it brings some humor to it, puts them in a better mood, and also gets them to think along a maybe a little bit of a different line in this area to think, all right, well, what do we get really creative about? What do we have to be really creative about in this sprint? What kind of tough solutions did we really conquer? Did we really nail in this sprint?

And I'm just theming around that loose theme of that surfer boy pizza from the last season. And then the last one, I couldn't have categories here without mentioning Hellfire Club. So the last one was Hellfire Club. And the prompt I put for it was, where could we bring more of kind of that Hellfire Club vibe, planning, teamwork, shared adventure, right? Just the fun.

Where could we put more of that vibe into our team and to how we operate? Now, this is getting them to think about something that might otherwise be a little bit of a uncomfortable thing to think about, right? Because Now we're getting into interpersonal dynamics. We're getting into how the team actually works and fits together. And that's why I chose this theme, because I wanted it to be just kind of a, even maybe a sneaky back doorway of getting their brains to start to examine, yeah, what would have made this more fun?

Or what would have made this, how could we have, I've asked often in retrospectives, what would it take for us to be the team that everyone else wishes they were on? Well, That's what I'm asking here, essentially. So I've got my five themes. And I even then went forward and created and kind of get some images for each one of those, like icons for each one of those things.

Just created a board and mural for this and put each of those things up. Had a big block space next to each one where people could put Post-it notes. So what I would do here in the retrospective is I'd introduce this. I'd give them the prompts for each of the section and say, all right, let's take a few minutes. Everyone can add Post-its to any of these sections, but try to think through several of them and put several of them up here on the screen or physical board if we're in the same space. But take a few moments here to think through each category and see if there's anything that you can think of that you would add to each area.

So we take, I don't know, five, 10 minutes to do that. normally time that, I just see when it starts to slow down. And there's generally a point there where you can kind of intuitively feel it and feel like, you know, the group's ready to move on. So whenever that time comes, I'll call a halt to it and I'll say, all right, now that we've done this, I want us to try to narrow down what's on the board. So let's give you each three votes.

And I do this usually with dot voting or something along that line. where they have three dots they can place on three different sticky notes across all five categories. And what I tell them is find the three that are the most important of all the things here, what are the three that are most important and put your vote on those top three. And by doing this, having the team vote on it, then we surface the most important three out of the entire group, right? It's not to say we ignore the others, but we're going to try, we can't focus on everything in our time that we have.

So, whether our top three, and then I start with the first one, right? So right now, all we've done is kind of the introduction of the sprint. We've done a transparency section. Now we move into the inspection. Now there's lots of different things you can do here, but what I put together for this retrospective was taking them through sort of a five whys activity.

So I would take that first one, I'd have them examine it and look at it and say, all right, let's ask the question why five times for this one. Why did this happen? whatever they answer, then we say, all right, well, why did that happen then? And we ask why, it doesn't have to technically be five times, but you need to ask it enough to where you get down to something that you can say, yeah, that's definitely the root cause, right? That's what's underneath all this. All that followed it, all that came afterwards was all stuff that came as a result of us making that decision.

So once we have our root cause, we can repeat that again for the other two. if we have time, but if we're starting to run out of time, I kind of watch my time box there. And once I realize we need to move into solutioning, then we'll move on into the adaptation portion. In adaptation, we just take each single one, and we kind of repeat this process of getting possible answers across the team.

So for the number one issue that you guys identified, here's our root cause. Let's take some post-its here. or let's take some suggestions of what we might possibly do to counteract this in the next sprint. So we get those things that come up. Then we'll talk through each one, and we'll try to build consensus as a team as to the most important step to take. So for each item, I want what's the one most important thing to do. So we'll identify that, again, as time allows, I want to at least do the most important thing.

If we have time for more than that, great, we'll get to the second and third. But I think it's so important to just, whatever the biggest, most important thing is, make sure you have an action item for that thing. And here's where I just caution you. It doesn't have to be, hey, we've knocked it out. We've cleared it. We've solved it in the next sprint. It just has to be that we've taken a step towards solving it, right? What's the old phrase, a journey of a thousand miles starts with a single step. Well, the same thing goes for our teams.

And this is oftentimes why teams get stuck, is they just feel paralyzed. Hey, there's nothing we can do about this. It's such a huge issue. Well, that's not true. What's the next step you can take? So take the next step.

Make sure that the team understands what it is. And make sure we understand who is going to be responsible for that. And do that for as many as you can get through. Then get to the closing the retrospective part of it. Kind of wrap up. Remind them, here's the journey we've taken, here's what we've uncovered, and here's what we're gonna do differently for next time.

And now those items, they should go straight into your next sprint backlog, not product backlog, sprint backlog, right? They don't need to be prioritized because the product owner has been with you, they should have been with you in this meeting, it's the entire Scrum team. So the product owner has weighed in as well. This has been a team collective decision. So now those items should go into your sprint backlog, and you should do something about them in this next sprint. That's the whole concept of the Kaizen comes first, right?

The good change should happen before we do anything else so we can get the benefit of it over a longer period of time. So that's kind of the idea here. And I wanted to give you that kind of really quick flyby to help you kind of see how to go about doing something like this, right? And I just picked one theme. I just picked Stranger Things because I thought it would be fun to work on. I thought it would be a fun kind of theme. And it might be fun for a team I was working with. But maybe that's not something that aligns to your team.

Maybe your team has a bunch of people who are really into cricket. Well, do a cricket-themed one. Maybe you have a team that's around the Academy Awards time. And everyone's talking about, and now people don't do this as much anymore, but. Maybe they're all talking about who's going to Oscars this year or something. Well, do an Oscar-themed one. Or it can be around anything. Do it around award shows in general. It doesn't have to be just Oscars, but do it around any kind of award show. And you can pick up different themes.

Again, if you're stuck, ask your favorite large language model and see what it comes up with. It's not all going to be gems that comes from that, but you can pick and choose and refine it, which is exactly what I did with my five themes for this. So I hope you see how easy it is to do that. It doesn't have to be complicated. You don't have to be extremely creative to do this.

You can make use of the tools that you have available to you. And as a Scrum Master, you can keep this fresh. You can tailor this to the team that you have. What is your team really into?

What's the theme that they would really resonate with? Choose that. Go with that. Create a theme around that and see what they think about it. Afterwards, ask them, hey, did this work all right? Did you like this? I hope that's been useful to you. If you like this and you want to hear more like this, come to our website to mountngoatsoftware.com and check out our courses that we're launching actually this week, Better Retrospectives and the Retrospective Repair Guide. Those are the two that we really want to have you kind of think about.

Come to our site, find out more about them. Better Retrospectives is all about just the expert level retrospectives course really gets into the heart of a lot of these issues at a very, very deep level. The retrospectives repair guide is taking the 10 most asked questions that we have about retrospectives at Mountain Goat Software and giving you really deep dives on how to solution those, how to problem solve those top 10 issues. And the great news for you is if you're listening to this in real time, right, when we've launched this, We're launching this as a two-for-one special. We'll not have that special again. So it's $99 that you get both of those courses. You don't have to pick and choose from them. You can give $99.

They're prerecorded. You can watch them at your own pace. This is for people who want this knowledge, who want these answers. And I know when I was a Scrum Master starting out, there was a lot of, I followed a kind of the pattern that Mike established with his sprint repair guide. I bought that when I was coming up as a scrum master because I needed answers to some of the questions that he had in that scrum repair guide. Well, take a look at the 10 that we have for our retrospective repair guide. Maybe you'll find one of those things that's really tripping you up and maybe just getting the answer to one of those is going to be worth the money for you. I encourage you to go to our site, check it out.

Don't miss this. It's a limited time cart that's opened. It's only going to be open for a week. So if you're listening to this when we launch it, don't delay, don't wait until next week. If you hear this next week, then you're running out of time. So make sure that you take advantage of the time that you have here so that you can get these two courses, two for the price of one here at our launch.

Again, we won't do that again. So I hope you found this to be useful. It's just a little taste of the kind of thing that's in those courses for you. And if retrospectives are something that you're struggling with, or if retrospectives are something that you just feel like, man, it really could be more. It really could deliver more for my team. Check out these two courses. I really think they're gonna help a lot of teams out there. That's why we put them together. So that'll wrap it up. I hope you've enjoyed this and we'll talk to you next time. on another episode of the Agile Mentors Podcast.