SarahC comments on Ask and Guess - Less Wrong
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I have a bias in that I really, really don't understand the "guess" mentality. Or rather, I see how it could develop but I don't understand how people once they are aware of the breakdown don't immediately say "hey! Ask is more efficient and less likely to lead to misunderstandings." While a culture that is a mix of Askers and Guessers will have a lot of misunderstandings (and likely more than a pure Ask or pure Guess culture), it seems that Guessers frequently have more serious misunderstandings due to poor guessing even when interacting with other Guessers. In contrast, Askers rarely have a problem interacting with other Askers in the same way. So it seems that utility is maximized with Askers. There's likely some biases coming into play in constructing this argument in that I'm heavily an Asker, and I've tried in areas I was more of a Guesser to move towards being more of an Asker because it just seems to work better. I'd be enlightened if someone could point out where my logic about ideal cultures breaks down.
Why should you ever be a guesser? Because guessers exist, and sometimes it's not in your interest to offend them.
I think what makes people tend towards guessing is a combination of personal temperament, childhood upbringing, and current environment. If you're sensitive to criticism and rejection, and you're good at picking up emotional cues (or at least if you tend to read emotional states into people; you may be wrong about those states), then you'll really want to avoid upsetting people with your requests. If you were brought up to believe asking is rude, you won't ask much.