Customers don't always know what they want. That's a given. But even if they do know, they may not always be able to communicate it clearly. That's also a given. Given these givens, you have a much better chance of comprehending your customers' needs and concerns if you're a skilled information-gathering skeptic.
Information-gathering skeptics are people who know how to draw pertinent information from customers, even if those customers don't know the information is pertinent or wouldn't otherwise think to mention it. These savvy skeptics also excel at eliciting information from customers who lack the inclination to answer a lot of questions. Information-gathering skeptics question not just their customers, but also themselves. They continually ask themselves whether they adequately understand the problem or situation or if they'd be wiser to ask more questions. But even when they are certain they understand, they ask themselves, "If I didn't understand, what would I ask?"
One way to improve as an information-gathering skeptic is to learn from those who are good at it. When I ask colleagues about people in the public eye who strike them as especially good at drawing information out of people, they often name Larry King, Barbara Walters, and Terry Gross on National Public Radio.
My own model of an information-gathering skeptic is Columbo, the TV detective who drives a beat-up old car, smokes a stinky cigar, and wears a rumpled raincoat even in desert-dry, 90-degree weather—and who is a master at asking questions. Invariably, he asks yet another one as he's partway out the door.
Columbo's approach is cleverness aforethought. He asks questions not just when he doesn't know the answer, but also when he does. Each additional question draws more information out of the suspect that helps him help them incriminate themselves. (Granted, this example isn't exactly analogous to gathering information from customers, but some of my software buddies insist it fits their organization perfectly!)
But it's not just the questions that are important; so too is the questioning. Columbo often seems befuddled, maybe even dumb—certainly not the optimal approach to working with customers. But there's something to be said about downplaying your expertise. When Columbo takes a low-key approach, minimizing his own knowledge rather than showcasing it, his questioning leads his suspects to feel full of themselves. As a result, they spew forth, and Columbo once again wins the day. Here are some other ways to excel as an information-gathering skeptic.
Take Nothing at Face Value
Always start by assuming that customers don't say what they mean or mean what they say. Information-gathering skeptics adopt a check-it-out-to-be-sure mentality by asking follow-up questions and seeking clarification, especially regarding terminology. Business and technical terminology lend themselves to multiple interpretations—and nothing beats everyday English for ambiguity. Therefore, it's best to start by assuming that customers mean something different by what they say than you think they mean. And the reverse is equally true: assume that what you say means something different to them than you actually mean. These assumptions may prove false, but checking them out is part of good detective work.
Focus Questions On the Problem, Rather Than the Person
The specific words used in posing questions can appear to challenge the customer's ability or intelligence, and customers who feel defensive are more likely to shut down than to flood you with useful facts and figures. So watch for questions that might sound less finger-pointing if oriented around the problem, rather than the customer. For example, instead of asking, "What problems have you experienced using this current method?" consider asking, "What kinds of problems have occurred with this current method?"
Focus Questions On the Person
This appears to contradict the previous point, but it doesn't, because information gathering entails a mix of problem-oriented and person-oriented questions. Used judiciously, questions that focus on the person—you-oriented questions, in other words—demonstrate concern for the customer. Questions such as "Do these interruptions make it difficult for you to get the job done?" or "What's the most distressing part of this problem for you?" often lead customers to reveal heaps of pertinent information. Most people are unaccustomed to others taking the time to listen to them. When you ask empathetic questions, and then listen non-judgmentally, you are likely to be amply rewarded with good information. I've found that simply asking, "What's a typical day like for you?" sometimes generates more useful data than a dozen questions directed at the problem or project.