The practice of asking creative questions

I’ve written on the importance of questions before, even going so far as to outline a combinatorial equation for asking better questions. But questions remain a complex and otherwise difficult problem to work around for creative thinkers.

Questions—particularly when they’re investigatory in nature rather than fact-finding—keep our thinking open. They create spaces for ideas to fill in our minds. When produced in an exploratory way with the intention of doing more than merely eliciting straight-forward information, questions are often what propel creative thinking forward.

Yet you probably struggle to come up with questions which feel impactful enough in a moment to warrant their investment. If you’re like most people, you end up asking more or less the same questions you always ask. “Why is this the way it is?” “What is this trying to do?” “How does this work?” Or, if you’re unfortunate, you find yourself without enough time to ask proper questions. Or you find yourself in an environment where questions outside of the status quo aren’t welcome.

Questions, like all ideas, evolve only from what you already know. If you fail to explore new questions, or to push your question-asking muscles, you’re bound to repeatedly ask the same questions. Often this restriction may be less helpful for creative output than you’d like.

The solution is the same as with any endeavor: we must expose ourselves to not only new and different ways of thinking, but also of forming questions.

The combinatorial equation is a good place to start, but it can be helpful if you go out into the world and observe how people ask questions elsewhere. At the coffee shop, why do they ask “How can I help you?” rather than “Do you know what you’d like?” How do children ask questions differently than adults? How do you formulate questions as opposed to your peers or friends? Why?

The best way to get better at anything is to observe and practice, it’s no different with questions.