The best way to get to good insights is to ask great questions. That’s after the “How do you make money ?” questions, of course. When asking C-level executives you often get answers that feel polished and rehearsed – “handled” information that might be written by corporate PR people. When asking managers, many of the answers feel guarded, as if the bosses will read them. I try to protect the names of salespeople and managers when they are really opening up, if the insights are helpful and business-building. (One trick is to always interview the company’s best sales person. S/he is typically a fearless rock star.)

Where I tend to get the real good stuff is not when I’m asking less about business success and failure but about emotions and feelings. The questions are hard to defend against. Hard to see coming. And they tend to be answered from the heart. When the guard comes down, the probes following the line of questioning are fluid. And by the time you back someone into the corner and they refuse to answer or waffle, your answer is obvious. Often accompanied by a wry smile. As the kids might say “awk-waaard.”

Pride is a good word to play with in your questions and probes. Admire another good one. Think feelings rather than behaviors. When the overall vibe is one of discussion and interest rather than probe and judgment you’ll find yourself in hallowed planning ground. Peace.