I think you have to have questions to back up your questions. Let's say you ask what town they want to live in and they say anywhere in the valley. And, let's say that the west side of the valley is near the mountains, and the east side has lots of upscale restaurants and entertainment.
I'd ask things like:
What does your family do for fun? If they reply with nature-lover things, I'd say: would you enjoy being near the parks in the mountains?
I'd ask where the people work. If the commute to the office from the west side of the valley is 1 hour, I'd ask, If you lived in the west valley, how would you feel about the hour commute?
I think it's a matter of working backward. Think of all the critieria you use to recommend something, then make a list of questions that will get the client to describe those critieria.
Do you spend more time in the kitchen or playing with the kids in the backyard? That might tell you if they want a big yard more than a fantastic kitchen. If it's the big yard, you wouldn't show them anything in the planned "city street" suburb.
I think a lot of times people give pat answers because they're afraid of looking silly, or they really haven't thought the issues through. If you can identify the criteria you use to recommend a product, you can usually find questions to ask that will help you clarify the client's needs.
Kathleen