Working dogs definitely guess at what their handler wants. "Running riot" is the term of art for when they do their own thing instead.

(advice on choosing a hunting prospect which I've run across: put something startling [alarm clock, etc.] next to the litter, and see how they react. Your best prospects should be among those puppies which first investigate, then ignore, the novelty. Those who never investigate probably won't be curious enough to easily train; those who never ignore probably won't be able to focus enough to easily train)

EDIT: maybe that wasn't what you were asking. Dogs obviously engage or disengage with other people based on whether or not they believe their person approves. But I don't think dogs ever (like someone asking a leading question of a third party not because they wanted to hear the answer but because they want their so to hear it yet are unwilling to say it directly) instigate a dyadic transaction explicitly for the effect it has on third parties. Horses for sure don't. (there is "dogpiling", but I think for dogs and am pretty sure for horses that that's a side effect of dyadic jockeying, not the social game monkeys make of it) What say the dog people?