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.
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