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Retrospectives and "strategic pessimism"

The 25th March is World Retrospective Day. I’ve just had my annual performance review at work. I thought I’d combine bits from both on the subject of “strategic pessimism.”

I got some great feedback from my colleagues as part of my review. But one thing surprised me: people thought of me as positive. I didn’t think of myself that way. I see myself as a pessimist. Not a doom-and-gloom, everything is terrible, kind of pessimist. A strategic pessimist: it’s a good idea to be aware of what might go wrong, so we can plan for it, and keep it in mind. Go off the happy path. Not obsess over it and worry about it all the time. But keep it in mind a little. I’m focused on the “now what”: how can we find workarounds or ways of avoiding the problem. And I think that’s where the “positive” description comes from.

I think this approach of mine comes through in some of the retro activities I choose to run for my team. I like to do activities that ask them to adopt a strategic pessimist approach. To consider the worst that could happen, then flip it and look at ways of achieving the best that could happen. Here’s an example.

Pessimise / The Worst We Could Do.

Explore how to ruin the next iteration for sure.

If this week had been ruined, what things would have happened?

  • What’s the opposite of those things?
  • What keeps you from doing those things?
  • Why?