A good trait of all analysts is to retain a skeptical approach to everything. Things are often different than they appear. One of my teachers also suggested that people have their own private logic so they will be consistent even if they do not appear to be on the surface. We must delve into their private logic. Things must be all connected logically like points on a line. Not your logic but theirs. Another source of information is people’s background. How did they arrive at the place you find them? A person, who has always been in one role and now finds themselves in another or always been in the same role, will have quite different views of the role and the world; important information. Interviewing a manager who has been in the role three weeks or ten years will provide quite different information. A good analyst does not take things at face value. One must check understanding by asking the question another way. You will be surprised at the information you get.
I agree that it might appear confrontational. What I was referring to was more of an an attitude of mind rather than a statement. Often by asking a slightly different question the confusion can be clarified. For example, someone tells you that a particular peice of software is too expensive. What does he really mean? Is it more than he expected, more than he had budgeted, more than the value he will get from it or too much in comparison with another product. All these are possible but like he really means only one of the above. Do not assume you know what he means.
This is a great technique, but needs to be done in an appropiate manner as otherwise, skepticism can be viewed as eith contrary or confrontational.