More than normal questionnaires, it takes unconventional "tricks" to get this information out of them. You have to analyze them and also the motivation of their audience --quickly. It's a journey into psychology. They frequently suffer from Cognitive Dissonance.
It's the distressing mental state that people feel when they "find themselves doing things that don't fit with what they know, or having opinions that do not fit with other opinions they hold." ... This bias sheds light on otherwise puzzling, irrational, and even destructive behavior.
Cognitive Dissonance wiki ref >
It's so common to be approached by a potential client and have them say, "Can you build us a web site or brochure by next Wednesday?" I answer, "Sure. Do you have images and ad copy ready?" "Uh. No. We don't know what content to put in yet." "Sorry. Then I can't deliver by next Wednesday." -End of Story- Common sense did not prevail. :)
A creative brief needs to be written. In most cases, this is the first time the client has sat down to write a plan of any sort. They want some "thing" but they don't know what they need. Suddenly, you're not just a designer but a business consultant, shrink, cop, and cheerleader.
As you mentioned, asking "why?" is a big part of mucking through clients imaginations and dreams to achieve what's REALLY important. This sometimes involves teaching them the difference between good design and bad. And why it makes a difference and matters. Establishing boundaries or limits of budget, delivery, and measure of "how good is good enough" should be set right away. That let's us know what we're up against and how to use creativity to make it happen.
There also are times when you should NOT work with someone. Design Therapy helps you screen out the losers. Only 50% of the people who approach me become real clients. You have to know how to qualify your leads.
One of my favorite but frustrating questions that a business partner asks me regularly, after I explain what I think is a wonderful idea, is: "Why should I care?" That's when I consider strangling him. But actually, he has my best interest at heart and knows if I can't explain my business idea so he "gets it", it needs further thought for reduction and clarity. So asking clients, "Why should I care?" takes several attempts before you'll get to the meat of what problem they really solve for people.
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