Today we live in a world where abnormal is the new normal, a work environment, social, even global environment where anything and everything can change in the blink of an eye. To survive, indeed to prosper in such a world, individuals and organizations must be able to perpetually adapt. That means they must be creative, and willing to explore the possibilities outside of their immediate world. Inevitably, the capacity to do any of this comes down to our ability to ask good questions.
While inquiry in general can be a positive force, you might wonder exactly what types of questions yield the greatest return. Undoubtedly, the specific questions must fit the person and circumstances. Yet there are patterns of certain types of questions that the most creatively successful people on the planet consistently ask, regardless of their sector or situations. One example is what I call “unprofessional questions.” The term came from a conversation with philosopher, author, and MacArthur “Genius Award” winner Rebecca Newberger Goldstein. Goldstein described to me how her greatest breakthroughs resulted from being willing to ask unprofessional questions, the kind that her field of philosophy said shouldn’t be asked. It wasn’t brash rebellion. It was simply that when the answers offered by her field didn’t fit real life, Rebecca had to get unprofessional—at least in her willingness to explore other ideas.
Having interviewed hundreds of the world’s most creative thinkers, including 65 other MacArthurs like Goldstein, I can report that asking unprofessional questions is a habit they share. So too is asking “questions of fit” (named for that willingness to consciously pursue that ‘Spidey sense’ feeling we all get but most of us ignore), “portraiture questions” (those questions that pull us back to see the immediate in the larger context we can so easily forget), and “change-the-W questions” (when we substitute the obvious who, what, when, where, or why in a question with one of its siblings, in order to get an unexpected and unencumbered view of the playing field). But there’s one type of question that plays a vital role in wrangling all the other types into relevance and more importantly, results. They’re called “depth check” questions.
Reflecting a comment many of her peers echoed, MacArthur Fellow and legendary choreographer Liz Lerman has said that when she’s working through a problem, creating something, or even just exploring, she likes to “think at both ends of the spectrum,” in other words at both the deep and the shallow ends of thhought. As I wrote in The Language of Man. Learning to Speak Creativity, “over time, the richest experience, indeed the most impactful ideas, come from spending time at both ends, not just one.” We tend to think of ourselves as players at one extreme or the other—as in, “She’s a deep thinker,” or “He’s a fast-moving surface thinker.” But we all benefit from swimming the full length of the pool. That said, if you aren’t aware of the depth your questions and thoughts are swimming in at any one moment, the value in your thoughts is hard to mine, and the risk of getting stuck at one extreme or the other deepens.
“Depth check questions help you gauge where you are and why you’re seeing what you see. They also signal when you may need to change depths to get the larger frame back in focus.” And they remind us that the greatest potential for breakthrough thinking and more, for impact, lies in being willing to move in and out of both ends, with a lot of time spent in the sometimes messy middle. To deal with uncertainty, to creatively ‘break through,’ to adapt and thrive ongoing, “You have to be willing to swim around, and be open to questions as you do.”
A version of this article originally appeared in the author’s Innovator’s Edge column for Inc. Magazine.