[sfg]

I've never heard of asking vs guessing culture before and don't know much about them, but, based on the article, I'd say guessing looks more transactional. It uses a shared history and remembers past favours ("I gave him soup, so I can seek to get his van", as the example in the article had it), which is really an implicit transaction without guarantee the other side will meet their end.

I am not even sure transactions are possible in asking culture, as it looks stateless. Askers just broadcast needs without reference to any past event, such as a favour.

This might be an equivocation, but, funnily enough, you said guessing is about understanding and for people to have an understanding is a way of saying they have a transaction (often implicit). For instance, "I gave him a pass on that, so now we have an understanding that I can do this".

[samus]

People in "ask" culture can provide context to their request, in effect making it transactional again. That works best if parties are not in a close relationship with each other, else the communication is already more contextual and "guess"-like than with loose acquaintances.