In one of the Dan Carlin Hardcore History series, he describes a discussion with a mentor who explained to him that the hardest thing about understanding history is forgetting how we know things will turn out. That impairs our ability to understand why people behaved as they did at the time, particularly because we over-estimate how likely the actual outcome was, and how obvious it should have been to people doing the choosing.
This talk by Nick Means does a good job of demonstrating how hindsight bias works in detail:
As it recommends, I am now reading Sidney Dekker’s The Field Guide to Understanding ‘Human Error’. The focus is primarily on things like air crashes and industrial accidents — which I find it interesting to read about anyway — but it also has lessons for anybody trying to learn from the past. The central lesson of Dekker’s book, that we can only understand the past if we make the effort to understand why the people then made the choices they did, seems applicable to policy and political analysis in general. In terms of organizing, the shift in emphasis from blaming individuals and treating the problem as solved to understanding what caused them (and likely will cause others) to make an error could be useful for reducing interpersonal conflict and improving performance.