Retrospectives NewsLetter 📰

🎨 Design Thinking Your Retro

Things in this Newsletter 🗞️

🌟 Editor's Note

Welcome to another Retro Newsletter. If this is your first time here, I highly recommend reading this newsletter first. It will give you the basics.

Sometimes, retrospectives can feel like we’re circling the same problems with the same conversations. What if we borrowed from another discipline to shake things up?

This week, I want to explore how Design Thinking principles can transform your retrospective into a 90-minute innovation sprint. Think of it as giving your team a playful, structured way to not just reflect on problems but actually design cool solutions together.

🌟  Continuous Improvement ideas

  • Meeting Sunset Policy – Every recurring meeting gets a “renew, retire or change” check every month.

🎨 Design Thinking Your Retro

I believe there is much to be learned when we take something from one context and apply it in another. I was just thinking that Design Thinking is all about empathy, creativity, and experimentation, and it has so many wonderful tools that can be used to problem-solve and ideate. Retros are about both of those, too, so here’s my idea for how to adapt its phases into a retro format:

1. Understand 

The first step in design thinking is to get clear on the problem to be solved. Either decide upfront on something you want to tackle or spend a bit of time thinking about your top problems. I might recommend deciding upfront because that way, you can spend the whole time focusing on a shared problem. Also, not all of your problems will benefit from this approach, but something like “Our branching and merging strategy no longer serves us” could be a good fit, or “this one piece of code is a tricky and entangled beast that we let get too big, how can we fix it” or “this part of our process seems long and over complicated how can we fix it?”

The design thinking toolkit offers lots of valuable ideas for this phase. I like the problem statement as a way to make sure that you can fully understand the problem you are trying to solve and whether it’s worth solving at all.

01_ProblemStatement_BASIC_EN.pdf270.72 KB • PDF File

2. Observe 

In this phase, we want to put ourselves into the mind of the person with the problem. And we want to observe, because by observing, we can eliminate the assumptions we might be making. We want to gather experiences and evidence.

I like the empathy map for this, but if you don’t have people to test with or talk to about their experiences, then you are in the realm of assumptions again. This could also be an opportunity for the team to share stories about how this problem affects them.

“Yesterday, when I went to check out this piece of code….. “ Telling stories can help to identify patterns, but can also help the team to get a shared understanding of where the problem really is and start to get the creative juices flowing.

Black and White Simple Empathy Map Brainstorm.pdf27.11 KB • PDF File

3. Define a Point of View 

Design thinking encourages us to ensure that we are solving the right problem for the right group; this way, we have a much better chance of success. So this phase is about being clear on the perspective you are taking. When we apply design thinking to product development, we may discover that there are different users with our problem or different perspectives, which could lead to different ideas and solutions. For technical and process problems, this might not be the case. It’s still helpful to take a moment here to make sure everyone is going in the same direction. These first three phases are primarily about staying within the problem space.

I like the define success tool here, as a mechanism to help think about how the team will know when they have succeeded.

4. Ideate 

Now that everyone is clear on the problem to be solved, you can lean into generating loads of ideas. The goal here is to look for many different possibilities. This creates space for opportunity and creativity, and you want to encourage diversity in thinking. Encourage wild ideas and defer judgment.

Brainstorming is great here. The more options, the better, as this allows you to use them to prototype. Pick one ot two ideas by dot voting or giving people fake money to spend to get an idea of where the energy lies.

5. Prototype 

This phase is great in design thinking because the goal is to create a cheap and fast version that can be tested with your users and that you can check in with them. It might not be as applicable in a retro space, but once you have a decision about one or two ideas, you can use the prototype phase to delve into details, or work on ensemble coding together, discuss, and draw out the solution to test your thinking and improve it.

You might also use this to design experiments you want to run and consider the different solutions you want to test.

6. Test & Reflect 

In the final phase, pick the experiments or the solutions you want to test. Check back in with your success factors and ensure that you are addressing all the ideas listed there. Assign pairs to the solutions and make sure that you close the feedback loop. When will we get back together to share the results and make a final decision about which solution or experiment is the one we are choosing.

Take a moment to reflect on the retro and consider if this way of thinking about the problem was helpful. Perhaps take a moment to share some appreciations and consider another problem that could benefit from this format.

Close the retro.

👉 You don’t have to run all seven phases every time. You could stop at Define + Ideate if you’re short on time, or stretch into Prototype + Test if the team is energised.

Quick Facilitator’s Tip

Timebox ruthlessly. Design Thinking can expand endlessly if you let it. To keep energy high, set clear timers for each phase and move the team forward. The time pressure actually boosts creativity.

🔥 Things you might like

  • 🎨 Resource: The Design Toolbox is packed with ideas and tools for each of the phases

  • 🎲 Facilitation Ideas: Liberating Structures – 33 wonderful facilitation techniques to learn from

Beehive is a fantastic newsletter platform that is easy to use, making it fun and straightforward to engage an audience with your message. Why not think about starting your newsletter: https://www.beehiiv.com?via=Joanne-Perold

My Remote Facilitation Course is for anyone who wants to learn how to create engaging online experiences for teams and people who need to work together, learn together or decide together. Here are the dates for the September course.

🧐 Facilitate or Plan with Jo

Did you know I can help plan your next retro or facilitate it for you? I have packages available for facilitation, planning, or being a sounding board. [email protected] is the email address to use for contact.

Did You Know? The first webcam watched a coffee pot. ☕

In 1991, researchers at Cambridge set up the first live webcam to monitor whether the office coffee pot was full, saving wasted trips.

Till next time,

Jo