Operations

Same Three Problems, Every Six Weeks

Thirty-one action items over six retros. Four done. The retro was a ritual that mistook complaint for improvement.

Same Three Problems, Every Six Weeks
Illustration · Deimar Gutiérrez

31 action items across 6 retros. 4 completed. 12 of them repeated, the same problem written down again and again by a team that kept agreeing to fix it and never did. I found the list on a Notion page after sitting in on an engineering retrospective at a series-B startup last quarter, where two of the three "things that went badly" were verbatim repeats of the previous retro, which had been verbatim repeats of the one before.

The engineering manager told me afterward that the retros felt productive in the moment, but he wasn't sure what they were producing. The Notion page answered that. Thirty-one items, four done, the rest written, agreed to, and forgotten within two weeks of each meeting.

The retro had become ritualized complaint. The format was fine. The team was honest about what had gone wrong, the conversation was respectful, the action items were specific. What was missing was the discipline of doing the work. The team had quietly learned that complaining in the retro was the resolution, not the start of one. The conversation produced emotional relief, which the brain reads as progress, which is why everyone kept showing up. It wasn't producing the work it was scheduled to produce.

The correction is mechanical and almost insultingly simple. Every action item gets a name and a date the moment it is written. The name is one person, not a team, not engineering, not we should. The date is a specific day. The next retro opens by reading the previous retro's action items out loud, and each named owner says, in front of the same group that watched them volunteer, whether the work got done. Yes, here's what changed. No, here's why not. Both answers are fine. Silence is not. This is the same accountability that separates a useful meeting from a standing calendar tax, a pattern I've dug into for meetings in general.

Within three retros this produces two effects. The action items that get written start smaller and more specific, because the team has learned the next retro will ask. Vague items like improve onboarding stop appearing, and specific ones like add a CONTRIBUTING.md by next Friday replace them. And the items that get written get done, because the cost of admitting in front of the group that the work didn't happen is higher than the cost of doing it.

The harder part is leadership. A retro that has decayed into ritual usually has a manager participating in the ritual instead of disrupting it. The manager hasn't made follow-through visible, hasn't asked the awkward question at the start of each retro, hasn't made it uncomfortable to repeat the same complaint with nothing to show. The format is rarely the problem. The accountability is always the problem.

If your retro has produced the same action items for three months, the retro isn't working. Start the next one with the previous list, by name, in front of the group. The first time will be uncomfortable. The third time will produce work.