For one of my classes, I was asked to put a file on the server. But when I saw the possible folder names, none made sense at a destination for my file. “Why is this one called ‘print’?,” I asked. “Why is this one named…why is…,” I continued.

This prompted one of my classmates to say, “Jamin was probably the kid who drove his teachers crazy always asking questions. But why? But why? But why?” This may be true.

“Why?” is one of the most powerful yet simple and telling questions you can ask. As a designer, this question will serve you well. It is a mixture of curiosity and health skepticism. As a former reporter, “why?” was crucial to digger deeper. So too is it with design, whether you’re interviewing or challenging your own judgments and decisions.

Often, however, people take the first answer and do not question further. Later in the day, I was doing directed storytelling with a group. I noticed that when other members of the group were interviewing, they would neglect to probe deeper into the answers given by the interviewee. For example:

Interviewer: “How did that make you feel?”

Interviewee: “It made me uncomfortable.”

The interviewee would then continue, because it seemed the question was answered. “Why?” would have been an excellent and simple follow up. And likely, “why?” could be asked several times to get the interviewee to really consider the meaning of her responses.

Too often we hear an answer and move one. This is definitely true of interviews, but may be true when we reflect on our own designs as well (e.g., why does this improve the experience?). As implied by my classmate’s observation, asking why may seem annoying, but it’s a great way to dig beneath the surface and uncover deeper meaning or, conversely, poor foundation.