According to Andrea Donderi, as described here by The Guardianís Oliver Burkeman, it depends on the culture in which you were raised:
We are raised, the theory runs, in one of two cultures.
In Ask culture, people grow up believing they can ask for anything ñ a favour, a pay riseñ 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 yesÖ 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. . . .
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.
Applying this to legal education, my sense is that law schools try to develop Askers into trial lawyers, while the die-hard Guessers among law students probably gravitate toward non-litigation areas. Off hand, I cannot recall in my experience a particularly effective litigator who was anything other than an Asker. On the other hand, I know a number of good deal lawyers who are Guessers. What do you think?