If you’ve ever realized retro time is around the corner again and sighed at the thought of another tired round of Start, Stop, Continue then you’re not alone. But here’s my confession: I love retros.
Like, really love them.
They’re the one space where the whole team hits pause, zooms out, and reflects on the work and how we’re working together. Since we spend so much time in execution mode where we are following plans, chasing down deliverables, and closing tickets, I think retros should be a chance to exhale. Maybe even laugh. Definitely connect. And ideally, do a little divergent thinking.
A great retro isn’t just another dusty ritual. It’s a moment of shared insight, creativity, and care. And when they’re working well, they can help a team grow in big ways.
Read the Room, Adjust the Format
One of the most powerful things I’ve found is that metaphor and playfulness open people up. Take the classic sailboat retro. I love this one. It works across different planning horizons: a sprint, a product increment, or even a launch. And the metaphors help people share nuance: wind in our sails, anchors holding us back, rocks ahead, treasure we’re sailing toward.
When I used the sailboat format with one of my teams, we were prepping for a big deployment. The metaphor helped reframe our blockers and risks in a way that was serious but still creative. But not every team vibes with the whimsy. If the stakes are high or the client culture leans more formal, I’ll adjust. For my team working with a fast-moving and focused start-up, I swapped the sailboat for a “pre-mortem” format. Same purpose, just more direct. It fit better for that context.
Here’s what I’ve learned: the tone of your retro should match how your team is feeling and what they need.
Remote-First? Make Something Together
If your team is remote or hybrid, the start of the retro matters even more. Quiet screens and video lag can flatten the energy. That’s why I put extra care into building connections right away with an icebreaker.
Shared canvases like Miro or FigJam are my go-to for mini-collaborative collage icebreakers. They let people create together and have a little fun. Some favorites:
- Decorate a birthday cake 🎂
- Let’s make some pizzas 🍕
- Dress the snowman for his ski trip ⛄️
- Get ready for our team camping trip 🏕️
These activities are quick, expressive, and energizing. They don’t take much time, but they bring the group into the moment and into a shared space together, regardless of their time zone or location.
The key is to keep it light, easy, and optional. People should feel welcome to join in, but not pressured.
What You Notice Shapes What You Facilitate
I try to plan around the conversations I observe that the team needs to have. This means listening for patterns in our conversations and collaboration, paying attention to silence, and watching for repeat blockers. These clues help shape the next retro.
If the team is tired or stretched thin, I might focus on celebrating wins or reconnecting with our purpose.
If we’re stuck in a cycle of the same issues, I’ll bring in a new format to help us look at things differently and find root causes.
If the team has performed beyond their own expectations, there’s an opportunity to examine whether we got lucky or there’s something we’re doing that we should take note of and bring to bear in the future.
When it’s done well, a retro isn’t just a check-in. It’s a small but strategic moment to realign and reaffirm.
The Ones That Didn’t Stick (and Why)
Not every format works for every situation or team. I’ve tried Rose, Bud, Thorn more than once, and it often falls flat. People struggle with the “bud” or the thing that’s starting to grow or show promise. Especially under time pressure. I still want to talk about things we should nurture, but I haven’t found the right way to do that in a short session.
Start, Stop, Continue is an old standby. It’s reliable, and teams know what to do with it. This format asks folks to name behaviors or practices they want to start doing, stop doing, or continue. It focuses on what’s observable, which is great for encouraging action. But it can also feel limited: it centers known problems and linear thinking, which leaves less room for creativity or curiosity.
Glad, Sad, Mad is another classic. It’s great for getting in touch with team emotions and surfacing the human impact of the sprint. But it can also veer into venting, especially when team morale is low. In those moments, the format can amplify frustration without offering a productive path forward.
If you’re looking to break out of the three-column retro rut, I recommend starting simple. Just two columns: Wins (what went well) and Opportunities (what didn’t go so great). It’s a lightweight frame that invites reflection and keeps things moving. When I’m trying to balance clarity with creativity, this one holds up.
Evolving the Practice
Retros don’t need to be fancy. But they do need to be intentional. As teams grow, change, or hit new challenges, the format should change too.
Here are a few questions I ask myself when planning:
- What kind of thinking does this team need to level up? Are we ready to consider solutions or do we need to name a problem?
- Are we stuck in a rut? Could a new frame shift our perspective?
- What tone will help the group feel safe, seen, and curious?
A good retro is more than a recap. It’s an investment in your team. It builds connection, insight, and momentum. And yes, it can be fun.
So next sprint, try something new. Add a metaphor, remix your format, or kick things off with a light-hearted icebreaker.