As one commenter explains it:
In some families, you grow up with the expectation that it's OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.
In Guess Culture, you avoid putting a request into words unless you're pretty sure the answer will be yes. Guess Culture depends on a tight net of shared expectations. A key skill is putting out delicate feelers. If you do this with enough subtlety, you won't even have to make the request directly; you'll get an offer. Even then, the offer may be genuine or pro forma; it takes yet more skill and delicacy to discern whether you should accept.This article in The Guardian continues:
Neither's "wrong", but when an Asker meets a Guesser, unpleasantness results. An Asker won't think it's rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no. Your boss, asking for a project to be finished early, may be an overdemanding boor – or just an Asker, who's assuming you might decline. If you're a Guesser, you'll hear it as an expectation. This is a spectrum, not a dichotomy, and it explains cross-cultural awkwardnesses, too: Brits and Americans get discombobulated doing business in Japan, because it's a Guess culture, yet experience Russians as rude, because they're diehard Askers.I am, without question, a Guesser. I hate asking favors of anyone, and worry about being presumptuous. The one thing about getting older, though, is that I'm learning to be more comfortable asking for things, and I'm also learning how to say no. Figuring out which one I am and realizing that some people fall into the other category goes a long way in helping me to relate with others better. It is a distinction that I am glad to have made.
Which one are you? Are you an Asker or a Guesser?
(I an indebted to Trent of The Simple Dollar for bringing my attention to the idea of Askers and Guessers.)