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Re:Choose Boring Technology (2015) by theptip on Sunday February 21, 2021 @01:11PM (#26215641)
> "what do we expect some of the new problems to be?"

A name for this I’ve heard (and use) is the “pre-mortem”; you can get folks in the right headspace for what you are suggesting by asking them to imagine they are writing a post-mortem after the proposed initiative failed.

A good way of surfacing failure modes / potential quagmires.

Re:Choose Boring Technology (2015) by Buttons840 on Sunday February 21, 2021 @01:23PM (#26215741)
> imagine they are writing a post-mortem after the proposed initiative failed

I was thinking more along the lines of "imagine they are writing a post-mortem after the proposed initiative succeeds". Even if everything goes perfectly, what do we honestly expect to have at the end? A system without problems? Nonsense.