sakranut comments on What are the optimal biases to overcome? - Less Wrong
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Which is entirely the wrong way to go about the problem. If this project is critical, and it's failure will sink the company, you really, really want to be in a position to handle the 25% cost overrun. If you have ten other identically-sized, identically-important project, then the 102.5% estimate is probably going to give you enough of a contingency to handle any one of them going over budget (but what is your plan if two go over budget?)
Thinking in terms of statistics, without any actual details attached, is one of the BIG failure modes I see from rationalists - and one that laypeople seem to avoid just fine, because to them the important thing is that Project X will make or break the company.
I'd suggest that this is a solvable problem - I've worked in multiple offices where meetings routinely ended early. Having everyone stand helps a lot. So does making them a quick and daily occurrence (it becomes routine to show up on time). So does having a meeting leader who keeps things on-topic, understands when an issue needs to be "taken offline" or researched and brought up the next day, etc..
So, to refine Decius' formula from above, you'd want to add in a variable which represents expected marginal utility of costs.
I don't think the problem here is thinking in terms of statistics; I think that the problem is attempting to use a simple model for a complicated decision.
[edited for grammar]
Both geeks and laypeople seem to use overly simply models, but (in my experience) they simplify in DIFFERENT ways: Geeks/"rationalists" seem to over-emphasize numbers, and laypeople seem to under-emphasize them. Geeks focus on hard data, while laypeople focus on intuition and common sense.
"Intuition and common sense" sound more like styles of thought process, not models. The models in question might be called "folklore" and "ordinary language" — when thinking "intuitively" with "common sense", we expect the world to fit neatly into the categories of ordinary language, and for events to work out in the way that we would find plausible as a story.