The formal terms for this difference are high context culture and low context culture.

https://en.wikipedia.org/wiki/High-context_and_low-context_c...

"Guess" culture would correspond to high context culture. You need to have a lot of shared context -- or be able to read a lot of clues to the context -- to infer what was really meant as a means to be adequately polite.

"Ask" culture would correspond to low context culture. It is often characterized as "rude" by outsiders but is also pro-diversity, such as New York City and American military culture.

Some people can navigate either type of culture, assuming they know what type of culture they are dealing with. Others assume the world works one way or the other and default to whichever one they grew up with, most likely.