How about not labeling people to begin with?
You're trying to pre-empt how to treat a person based on an arbitrary label.
Firstly, those labels are not absolutes. There is no reason to expect that a person is one and only one of those labels. Secondly, pre-emptive judgment of such a label is nothing short of stereotyping a person based on some approximated ...
Observe whether they say "No"
An asker is very direct, and sometimes to the point of being too blunt, and has no problems with people telling them "No", but guessers are a lot more subtle, and have serious problems both receiving and giving "No"s.
That is the fundamental difference between an asker and a guesser. A guesser ...
If I ask, they find it hard to say no. If I ask it in a begging
manner, it is even harder for them to say no, even if they are
As you already identified, the problem is that it is hard for them to say no. So instead of begging (and therefore making it even harder) you could focus on trying to give the other person the feeling that it is ...