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lucidfox comments on Ask and Guess - Less Wrong Discussion
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A guesser is not limited to waiting for others to guess what they want, but they will not ask until they have guessed that the request would be well received.
The relative advantages of each depend on the culture in which they're operating. If you're in a strongly guess-oriented culture, being an asker would be very disadvantageous, whereas in an ask-oriented culture, it would be disadvantageous to be a guesser.
It would be disadvantageous to "be a guesser" in the sense of feeling obligated to guess instead of ask, but applying some guessing can be advantageous in an ask culture. By avoiding asking people questions when the answers would make them uncomfortable (no I don't want to pick you up at the airport, no you can't come to the party) you are more pleasant to be around.