You want to find out about the person, so ask questions that tell you about their thinking, needs, wants, and goals. For example:
1) Schooling – what did they like or dislike about it, favorite teachers, favorite subjects, etc What might you like to study in the future?
2) Talk about shopping – how often do they go, what do they get, what are they saving for, are the a compulsive shopper, etc
3) What shul do they go to? How do they like the davening? How’s the kiddush? What kind of people go there (careful with this as it may lead to L”H)?
4) Hobbies and leisure – recent vacations? where would you like to go? What kind of hobbies? Play sports or exercise? Web usage? Do you use the CR?