JO’s Newsletter 📰

Hello, and welcome to the retro newsletter. I’m late with my newsletter this month. Things have been a bit crazy, but I’m back. As a treat, I recently facilitated a retrospective for a management team, and even after more than 15 years of facilitating retros, I still make mistakes. So here I’m sharing the mistakes I made and the learning or the realisations about what I should have done instead.

What's in this newsletter

• Mistakes part 2 🙈

• Context: Setting the Stage for Reflection

• Mistakes and Learnings: What Didn’t Work as Planne …

• Improvements: Retro part 2

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• 💡 Things you might like

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  • 💡 1,2,4 All

Mistakes part 2 🙈

Context: Setting the Stage for Reflection

I recently facilitated a retrospective for the management team of a large financial services division. This was the first retro for this group, although they were familiar with the concept from other contexts. The goal was to reflect on the past two years of their new way of working—what was going well and what needed improvement.

The team consisted of 12 people, mostly in the same city, with one remote member (or so I thought). I structured the session around four key areas: Processes, People, Technology, and Product, asking participants to reflect from the perspective of "Proud" and "Worried." They had time to prepare their thoughts in advance.

We had four hours together, and I set the stage with two opening questions and working agreements. After gathering data using sticky notes and visualization, we moved into pattern-spotting to generate insights. Just as we started diving deeper into one of the key topics… we ran out of time.

Mistakes and Learnings: What Didn’t Work as Planned

🔹 Unexpected Remote Participation
I planned for one remote participant but arrived to find two. This isn’t the end of the world, but making sure people can contribute easily and see what’s happening is very important. Having a second person also ended up taking more time, especially for the gathering data part, because I replicated all of their ideas on sticky notes for the in-person people. If I had known I had two remote people, I might have worked with a remote tool for visualisation like Miro.

🔹 New and Unknown Team Dynamics
I didn’t realize one team member was very new and another was a contractor. This can impact team dynamics, how people communicate, and what they share. Luckily, the contractor is well-known to the team and me. The other new person seemed confident and easily able to contribute, so that was good.

🔹 Overwhelming Volume of Input
Since I gave them time to prepare, they arrived with a LOT of data—more than I anticipated. I didn’t set limits on how much they could share, which led to an overload of sticky notes and topics. When this is visualised, it can be very overwhelming, and there is definitely not going to be enough time to talk about all of it. We managed to gloss over everything so everyone had an idea of what was there before we chose something to dive into, but it would have been better if I had limited the amount of stickies.

🔹 Big Group, Small Voices
With 12 people in a single discussion, dominant voices took over, and quieter ones were left unheard. To balance participation, I should have split them into small groups earlier.

🔹 The scope Was Too Broad
Looking back on two years in one session was ambitious. What I should have done was contract for a series of 3 retrospectives, each focusing on a different aspect of what they wanted to improve. That would have been enough to get them started with good actions and created a rhythm of improvements that they could build on.

Improvements: Retro part 2

Recognizing the gaps, I went back to complete the facilitation and made these improvements:

✅ Shorter Check-In – I streamlined the opening to move into discussions faster.

✅ Recap & Small Group Work – We started with a brief recap, and then small groups discussed and synthesized key takeaways before sharing back.

✅ More Voices, More Balance – Using smaller groups throughout, everyone had the space to contribute. Each group brought their top three ideas to the larger discussion.

✅ Focused Options – Instead of an overwhelming number of topics, we narrowed them down, making it easier for the team to prioritize and take action.

By the end, they walked away with clear actions—and I walked away with valuable lessons for my next retro.

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💡 Things you might like

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🧪 Session Lab

Session lab has this fantastic library of all things facilitation.

💡 1,2,4 All

Here is a link to the wonderful 1,2,4, all structure from Liberating Structures. This is something that I could have used as a facilitation technique to go from lots of ideas to fewer ideas. Check it out and see how you could maybe use it.