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".
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".