My most important retrospectives were horrible

I’ve got a confession to make: I think fun in retrospectives is overrated. And I never bring cookies, when I facilitate.

Don’t get me wrong, I prefer having a good time to moping about and yes, I prefer participants to be in a good mood. Light hearted people are more creative and willing to try new things.

But all my most important retrospectives – the ones I still remember years later – were horrible! Or at the very least deeply uncomfortable. That holds true regardless of whether I facilitated or was a regular participant.

The important retrospectives, the ones that really counted and made a profound difference were about troubling topics: When something or someone wasn’t working out despite everyone’s best efforts. These retros had a big impact like teams dissolving; people leaving teams or even the company. That’s category of events I’m talking about.

Something like that is decidedly not fun. But it’s necessary to have these conversations. I’m grateful to people who have the guts to bring up the crucial topics even if it hurts in that moment. After the dust has settled everyone is better off, because a harmful situation has turned into a new beginning. And work in general, not just retrospectives, has a chance to be fun again.

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