Or: what are you actually trying to do?
One thing I’ve noticed is that when I’m trying to solve a problem, the answer often becomes apparent when I stop to consider what it is I’m actually trying to do. This is hardly a new concept, I know. But so many times I’ve caught myself and others get stuck because they’re trying to solve a problem that doesn’t need solving. It’s not so much about “thinking outside the box” as much as it is thinking about what the box is.
One of the better ways I’ve found to do this is to not let customers speak in technical terms. More correctly: get them to describe features in business terms. So instead of saying “I want this page to show me x, y, and z when I click the foo button”, get them to say “I need to be able to tell my boss how much this simulation cost.” It may turn out you can solve that problem in a much easier or more reliable way.
This isn’t limited to technology, either. Half of answering a question is figuring out what’s really being asked. It’s not always the same as the words used. Just yesterday, I started to ask my boss about the setup period for a conference we’ll be at next week. Then I stopped and said “let me ask you my real question: do I have time to grab lunch with a coworker or should I go straight to the venue?”
Even though I long ago learned that what’s said isn’t always what’s asked, I still find myself on the wrong end when I ask questions. I’ll catch myself asking two or three questions and then getting to the heart of the matter. And of course, if the person I’m talking to doesn’t realize what I’m actually asking, they might give an answer that doesn’t work in the context of my real question.