Tyler Cowen points to a fascinating cultural etiquette clash:
This terminology comes from a brilliant web posting by Andrea Donderi that’s achieved minor cult status online. We are raised, the theory runs, in one of two cultures. In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid “putting a request into words unless you’re pretty sure the answer will be yes… A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t 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.”
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.
I suppose neither is “wrong,” but I’ve found that being an Asker is almost always the superior choice. Boldness is rewarded in many facets of life. Passivity leaves you frustrated and mad that the pushy guy got the job, the promotion, the girl, you name it. Being unwilling to say no gets you walked all over.
Really, being a guesser is just a way to shield your ego from rejection.
Just about everyone could benefit by moving towards the ‘Asker’ side of the spectrum. Some questions: what is the optimal point on that spectrum? Is it the same for everyone? If not, what kinds of people should be more on the guesser side?