Given that retrospectives are all about reflecting on the past with a goal of continuous improvement, it felt fitting to take a moment to reflect on retrospectives themselves: How have they changed over the years, what mistakes are most common today, and how can we improve retrospectives looking forward?

To answer these questions, we turned to retrospective expert David Horowitz, founder of Retrium and co-author of the second edition of Agile Retrospectives: A Practical Guide for Catalyzing Team Learning and Improvement. In this interview, Horowitz shares his thoughts on the evolution of retrospectives, including tips for combatting the most common challenges today and his predictions for the future.

Q: Can you tell me a bit about your background and how you narrowed your focus on retrospectives?

David Horowitz: I've been in the software development space for almost 20 years now. I started my career as a software engineer and quickly realized that what interested me just as much as the technical challenges, if not more so, were the people challenges. 

So about eight or nine years into my software engineering journey, I transitioned from writing code to agile coaching. And I soon ran into the problem of how—when you're working as I was in a globally distributed organization of thousands of people—do you learn together to produce better-quality software that meets the needs of your stakeholders and end users?

That question led me to introduce the practice of retrospectives at the organization I was at—only to fail miserably. I didn't know what I was doing with running retrospectives, especially given the cultural differences we had with a global workforce and the size of the groups I was working with. So I started on my journey of learning how to facilitate distributed retrospectives more effectively, and I soon realized that, from a tooling perspective, this was largely an unsolved problem.

That ultimately led me to start Retrium—to figure out how to make retrospectives easier and, in a way, democratize the retrospective facilitation process for everyone. 

Q: You first noticed that many organizations struggled with retrospectives years ago. Do those same challenges still exist today?

DH: I think we've made tremendous progress, but I also think there's still a long way to go. 

One sign of progress is that the number of teams that run retrospectives now—as opposed to 10 to 20 years ago—is enormously higher. We're all taking the time to learn now instead of assuming we know what we're doing from the start, so that's a huge win. 

Beyond that, basic facilitation practices have also improved. When I started my career, I didn’t see many people using things like sticky notes to facilitate conversation or dot voting to prioritize discussion topics. Now, it seems that more people are aware of those things (although whether they're using them successfully or not is a different question). 

But the rise of these techniques has also caused some teams to miss the point of retrospectives. For instance, maybe a team used a “start, stop, continue” or “mad, sad, glad” technique—and they go through the motions, add sticky notes to a board, and call that a retrospective. 

While these are effective techniques to start your journey toward running a successful retrospective, using them on their own is simply not going to yield the results you're looking for. It’s an incomplete approach, and there’s much more to leading effective retrospectives.

Q: Given that there’s still a lot of room for improvement, what are some of the greatest mistakes organizations make in retrospectives today?

DH: I could spend hours discussing this, but I’ll limit myself to three of the most common mistakes I see. 

Mistake #1: Attempting to tackle too many topics

Many teams have this practice of listing out the number of challenges they're facing and trying to tackle each of them in the retrospective. If you do that, you limit the amount of time you can talk about each topic, which means you have a very simplistic and surface-level conversation. 

Instead, I recommend limiting the scope of the discussion down to just one thing that your group is really struggling with so that you can spend the rest of the time diving deep into that challenge. By taking the time to really understand that problem, you’ll be able to come up with an action item or an experiment at the end of the retrospective that actually addresses the root of the problem.

Mistake #2: Not following through on action items 

What happens after the retrospective is done is equally important, if not more so, than the retrospective itself. At the end of most retrospectives, teams come up with some sort of action or experiment to bring into the next iteration. And they have good intentions, but life gets in the way. They either forget or intentionally deprioritize the work item that came out of the retrospective. And by pushing that off, they devalue the retrospective, which means they’re going to place less emphasis on the action the next time, and so on and so forth, until people believe retrospectives have no value. 

And they’d be right—if you actually aren't doing something about the problems that you've identified, the retrospective really isn’t that valuable. But the solution is not to stop running retrospectives. The solution is to actually follow through on the retrospective after you've completed it.

Mistake #3: Managers insisting on joining the retrospective

One other mistake I’d call out is when managers insist that they join the retrospectives. Good retrospectives tackle thorny issues and, in order to have a constructive conversation, rely on psychological safety. Psychological safety is a necessary condition before the retrospective starts—it’s not something you can magically create in the retrospective. But it is something that you can easily destroy in the retrospective even if it existed before. 

I’ve seen a team start the retrospective, and then the manager jumps in, and all sorts of interesting dynamics start to happen. On average, people start to get a little nervous about saying the wrong thing and the retrospective loses a lot of its value. But the problem is not the manager actually joining the retro; it’s that the manager insists on joining the retro. If the opposite is true—the team is inviting the manager in—that’s an entirely different case.

Q: The rise of remote work has undoubtedly altered the retrospective experience for teams. How can hybrid or remote teams run effective retrospectives?

DH: I’ve been working remotely for 20 years now, well before there were tools like Slack and virtual whiteboards. The tools available today are far more advanced than they were then. We used to just have a conference call without video, and it's hard to do a retrospective effectively that way.

We now have virtual whiteboards and visual collaboration solutions, like Lucid, to help distributed teams collaborate during retrospectives. These are very useful for experienced facilitators or those who want to design their own retrospective experience.

And then another type of tool has emerged that’s purpose-built specifically for retrospectives, like Retrium. These tools guide teams through the five phases of a retrospective, helping facilitate the experience and educating teams along the way.

Both of these categories of tools are incredibly valuable for remote teams, or any team, really. Which tool you use depends on factors like your facilitation experience, the time you have available, and your desire to customize the experience. 

Q: We’ve covered the past and current state of retrospectives. What do you think the future state of retrospectives looks like?

DH: To answer that question, let’s turn to the Cynefin framework. This framework classifies problems as clear, complicated, complex, and chaotic. I won’t get into all the details, but the basic idea is that some problems have simple, known solutions. Maybe there’s a manual or a standard operating procedure to follow. Other problems are more complex, where you have no way of knowing the solution in advance; you have to learn as you go. 

I bring this framework up because as time goes on, our world is changing faster and faster. Whether it's economic upheaval, the rise of AI, political uncertainty, climate change—the list could go on and on—the events around us are making the way we work and do business more complex. And complex work requires taking the time for learning events like retrospectives to see if you’re on the right course. 

The more uncertain and volatile the world gets, the more important retrospectives will be. Teams and organizations who put in the effort to improve their retrospectives will be better positioned to navigate the growing complexity.