Retro Roulette

January 5, 2019 • on learning and process

Frequent reflection on how we can do better work in better ways is one of my favorite things about my team’s culture. For a long time, this took the form of monthly “retro” meetings where we all get in a room for an hour and talk about what’s been fun or frustrating, and how we can do more of the former and less of the latter. However, as my team grew to around 10 people, we noticed a creeping resistance to speaking up which led to conversation feeling more artificial. This only got worse as we grew past 20, when we finally put the meeting out of its misery. I really missed these opportunities for reflection, and want to share a new approach we’ve been trying to encourage this kind of reflection on larger teams, with which we’ve seen promising results. I call it Retro Roulette.

The motivation for this was simple: if one big conversation wasn’t working, let’s try a bunch of smaller ones, but inject a bit of randomness so that folks still get to hear from colleagues they don’t work with every day.

The Method

It works like this:

  • Once a month, we put the names of everyone interested into a hat and draw pairs. (Not a real hat, I’ve modeled this in Ruby with names.shuffle.in_groups_of(2))
  • Each pair gets coffee, lunch, or just chats that day about the usual retro topics, or whatever’s on their mind.
  • If topics or ideas come up that someone wants to share or discuss with the whole team, we have a Slack channel for that.

It’s worked out pretty well so far: participation is optional, but most folks who joined at first continue to do so. (I’m still looking to reach those who haven’t given it a try.) There’s usually a post or two in our chat channel afterwards about something someone found interesting. And for me personally, it’s been a great opportunity to engage with teammates I don’t work with regularly.

Some Slight Modifications

Since its inception, we’ve made a few changes to Retro Roulette:

After starting with pairs, we’ve changed to conversation groups of three people, which the team almost universally preferred. There is research to suggest the ideal size of a conversation is around 4-5 people, so we’ll likely try at least one more increase.

And after starting without much direction to the topics of conversation, we’ve since tried suggesting topics, often pulling from resonant topics that came up by chance among earlier groups. Some of my favorites have been:

  • What’s something you want to try—in work or outside—in 2019?
  • Where do you want to be next year? In 3 years? How can your colleagues help you get there?
  • What’s the one thing we as a team could do differently, that would make everything else easier? (Inspired by the book The One Thing)
  • What’s a product or product team you admire? What do you admire about them? What would that look like here?

If you try (or have tried) something like this on your team, I’d love to hear about it.