By occasionally expressing general observations, you can often generate information beyond what you can get from questions alone. For example, you might comment, "This seems like a particularly difficult time for this department" or "It sounds like priorities are always changing here." People rarely let such statements pass without adding their own perspective, and their responses may be valuable.
Use Silence as an Information-gathering Technique
A month ago, I wouldn't have thought to include this suggestion. Then I visited a company where I met with each of several customers regarding a project that had just received the go-ahead. I asked the first customer: "What's your reaction to this project?" He responded enthusiastically. I waited to see if he wanted to add anything. After several moments of silence he added, "But I have some concerns." And he offered some important suggestions that could prevent the project from racing breathlessly to never-never land.
Intrigued by how much he had disclosed without being asked, I used the same approach with the other customers I met with. The result was the same. All of them enthusiastically supported the project. Each then described some potential pitfalls, along with suggestions about how to avoid them. Unprompted, these customers offered information that I wouldn't have known to ask for.
The lesson: Sometimes, remaining silent is the best thing an information-gathering skeptic can do. Information-gathering skeptics are a valuable part of any team. By drawing otherwise inaccessible information from your customers, these undercover detectives can help you deliver better, more relevant software to your extremely satisfied customers.