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The part where he talks about forecasting the probability of an event being hard is interesting. Does that change our thinking on the decision making process for groups in terms of what the statements we create are for those decisions? Should we try to create statements that are more qualitative then?

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It is hard but you can train it. I think you should always leave space for qualitative reasoning (rationales) but also ask for the point forecast. The rationale will suss out any problems someone is having with the more quantitative piece, IMO

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Second the recommendation about reading "Quit". Imagine most people here have. Very interesting useful read.

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