I grew up in China and the guess culture was predominant there. It was quite a culture shock after I came to the US. In a training session back when I was in IBM, the VP of marketing told us a story about the ask culture: he was an American-born Japanese. When Lou Gerstner asked him what he wanted, he instinctively tried to be humble. Lou cut him off and said: I can't help you if you don't tell me what you want. Come back in X months when you know the answer. The next time they met, the VP told Lou that he wanted to be an executive, and he got promoted soon. Another thing I learned in the training session was that leaders have different styles but all the executives demonstrated only one of the four key styles: direct and decisive.
As time went by, I found it was much easier to adapt to the ask culture. I also found consistency matters more than the styles. When I consistently ask with good intention, people would not take offense.