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Retrospectives NewsLetter đź“°
The team challenge issue.
Things in this Newsletter 🗞️
🌟 Editor's Note
Welcome to another Retro Newsletter; I’m piloting a new format and would love to know what you think.
🌟 Continuous Improvement ideas
We don’t have to wait for retros to make improvements to what we do or to start thinking more deeply about our processes. Asking the team a question every week that they can reflect on can create a habit of team learning and introspection. You can even create a channel in your chat tool and throw it in there on a weekly basis.
Here’s an idea.
“What’s one assumption we made this week that didn’t hold true?”
“What’s one thing that we did this week that could be easier for us?”
🧱 The Team Challenge: Building Connection Through Play
Sometimes, what a team needs is to learn something specific or to have their thinking about something challenged. In cases like that, when I recognise that a regular 5-stage retro isn’t going to cut it, I look for something different, or I create an exercise or learning experience for the team.
Lego, puzzles, cards, and fun have all made appearances in my retrospectives—not just for fun but to spark deeper learning, build connections, and help teams grow stronger together.
Sometimes, what a team needs most is a shared experience.
One that nudges them out of their routine, challenges their thinking and beliefs about something or gives them new perspectives to consider. That’s where the Team Challenge comes in.
🧩 Why a Challenge?
I started using team challenges as retro themes when I noticed certain teams were stuck—not in process, but in energy or thinking. Some needed to know what they could achieve together. Others needed to learn how to work as a unit under pressure. And some were just forming and needed a fast way to get to know each other’s working styles.
Instead of telling them what I thought they needed, I gave them a challenge that would show them or give them an experience that we could debrief together and learn from.
🏗️ A Few Favorites:
I’m not going to share all the examples here, but I will give you a few that stand out and some ideas for creating them for yourself.
1. The Lego Win
One team was struggling to collaborate. They were great at dividing things up into tasks for specific people and assigning those tasks. The team lead did all the assigning, and the team was demotivated and plodding along. I wanted two things for them
A task that forced them to work together
An achievement that allowed them to feel what it was like to win together, doing something that they could only do together.
I brought in a simple Lego build challenge—something they had to complete together but needed to happen in a specific and challenging timeframe. I got them to run it twice; the first time, they didn’t make it because the time frame was tight, but also, they hadn’t figured out how to do it together, so they weren’t all part of solving the problem. The team lead was again doing most of the work without delegating or allowing others to jump in. Then I gave them a few minutes to change their way of work, and they did it again. I might have made some suggestions for how to include people and go faster. This time, they nailed it. That feeling of solving a problem side by side, of physically building something together, created a decisive shift in their dynamic and created an opening for a deep and meaningful debrief about how they worked differently in the two scenarios and what they could take into their everyday work. It was rich and powerful.
2. Three Sets, One Timer
Another team got a timeboxed challenge: build three different Lego sets as a team within a limited time. There were no instructions on how to divide the work—they had to figure that out. Again, I ran two versions of the exercise, one where they tried to work asynchronously with different people working on different sets. At the end of the time frame, they ended up with three half-built sets. Then we ran it again, and this time, they worked together to finish one at a time before moving on to the next one. They didn’t finish all three but did have 2 out of three instead of none. They discovered that when multiple people work on a single problem, not only is it faster—but the solutions are more robust. Roles naturally formed. Communication sharpened. We debriefed in detail, and this gave them a feeling of what different could look like and how they might start to do things differently in their work.
3. The Riddle Reveal
For a brand new team, I gave them a complex riddle to solve. No guidance, just a shared puzzle. I actually used the Einstein riddle because it’s a great yet tricky logic puzzle. It’s challenging to solve, and there are many ways to go about it, so it surfaces many nuances in team dynamics. The goal wasn’t the right answer—it was to observe how they tackled it. Who took the lead? Who hung back? How did they deal with uncertainty or frustration? It was a window into team dynamics under pressure—and an excellent springboard for conversation about roles, communication, and expectations. This was a great way to start to observe and talk about the team dynamics that might play out later when the team was under pressure. We could use this as a way to update the working agreements or to create principles for communication.
Each of these challenges was intentionally designed. Not to test the team but to surface something important, teach them something new, or give them the opportunity to feel something together. These experiences create a kind of team memory—something they can refer back to and continue to learn from.
Gerry Weinberg wrote three excellent books about creating learning experiences, and you can find them on Lean Pub, here is the first one
🧪 Try This in Your Next Retro
Want to run a Team Challenge yourself?
Start small:
Decide what the learning goal is
Think about an activity that could surface that problem or create the opportunity to learn something about that goal
Bring a puzzle or simple building task.
Frame it with curiosity, not competition.
Step back and observe; use your observations to generate debrief questions related to the learning goal
Then, debrief:
What did we notice about how we worked together? What surprised us? What would we do differently next time?
It’s not just play—it’s learning, connection, and growth in disguise.
Want help designing your own team challenge? Hit reply or drop me a message—I’ve got a stash of ideas I’d love to share.
🧠Quick Facilitator’s Tip
Silence is a tool: next time the room is quiet, count to 5 before jumping in—you might be surprised who speaks up.
Names: If you are facilitating a group and don’t know people’s names yet, get everyone to check in by writing their name on a sticky drawing a picture and leaving it in front of them. That way, you can use peoples’s names and learn them as you go.
🔥 Things you might like
Beehive is a fantastic newsletter platform that is so easy to use and makes it fun and easy to engage an audience if you have something to say, why not think about starting your newsletter: https://www.beehiiv.com?via=Joanne-Perold
Lego often does sets where you can make three different things from one set. I love these because I can use them in so many different ways
Did You Know? The first computer bug was literally a bug—in 1947, Grace Hopper found a moth trapped in a Harvard Mark II computer, coining the term "debugging" in the process.
Till next time,