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.

Two methods for asking better questions

A favorite quote of mine from Socrates goes: “Understanding a question is half an answer.”

Famous American inventor William Edwards Deming echoed Socrates by stating: “If you do not know how to ask the right question, you discover nothing.”

The importance of both these quotes cannot be overstated, however both what Socrates and Deming’s say can easily be misunderstood.

Undoubtedly asking and exploring many questions is beneficial, as doing so is a core attribute of creative problem solving. As Einstein famously said: “I have no special talent, I am only passionately curious.” To be curious is to ask many questions, but what these quotes are undoubtedly hinting at is the value of asking and understanding the right questions. It’s not enough to simply be curious and ask many questions.

What matters is being able to understand the questions you’re asking and learning from them regardless of their answer or outcome.

What does it mean to ask the right question? What makes one question better than another? How do you start to understand the questions you ask?

First, you must pursue investigative questions, not factual ones. In his book Beyond the Obvious, Phil McKinney explains the difference between these two common types of questions can quickly end, or empower, your pursuit of new ideas or understanding.

McKinney writes: “By definition, a divergent question means that there is more than one correct answer (unlike factual questions). It cannot be answered with one phone call, or a quick check at some stats or figures, and forces us to investigate all of the possibilities.” To invoke creativity you should seek to ask questions with no common, quick-to-address answers; questions which will allow our thinking to diverge rather than converge. The benefit of focusing on investigative questions is their ability to help connect ideas which you may not first perceive as having been connected, rather than mere information gathering.

The next thing you must do to ask better questions is think about the attributes of the questions themselves. Getting meta is valuable for understanding the possible answers you might uncover.

Asking why the sky is blue is different than asking why we perceive the sky to be blue. But why? In one question the emphasis is on the science of our atmosphere, while the other focuses on the human body. But how often do we consider these types of attributes within the questions we ask?

When you’re asking a question, don’t merely ask it, ask what you’re asking and break down each component of the question in order to either invoke other questions or to better understand the question you’re already looking at.

One way to break questions down is to ask additional questions about the questions you ask.

I typically do this by addressing the five Ws: who, what, where, when, and why. Who is this question for and who does it matter to? What is this question trying to answer, what might it be overlooking? Where does this question commonly occur? Is there anything I might learn from looking at where the question is asked? When does this question come up? Was there a certain prompt which influenced it over another possible question? Why does this question matter to begin with? Why not the opposite of this question?

The more you look into the very questions you find yourself asking, the more you’ll begin to understand them. And the more you understand the questions you find yourself asking—including the way you ask them and the structure that makes them up—the more you are to ask better questions in order to undercover new ideas, new ways of thinking, and ultimately creativity.

Getting past when you can’t take your ideas further

Yesterday I wrote about how to explore ideas quickly by asking “What comes next?”

It’s a great way to recognize the importance any question has in the role of creative thinking. Questions lead us down new paths, good questions help us plot where we are on the route between powerfully creative ideas and subpar ones.

Landing at a place where there are seemingly no more questions for the work you’re doing can be dangerous.

“If you don’t have any more questions for what you’re doing, that doesn’t mean you’ve arrived at an end point. It means you aren’t looking in the right places.”

Answers that lead to a place where there aren’t any new questions to ask are dead-ends. As creatives, that means we’re either not stretching our thinking or we’re on a path that has few creative possibilities.

How do you overcome a place of stickiness with your ideas, when there just aren’t enough questions to explore?

One way is to backtrack, to look at the question you asked just before you got stuck, then rephrase that question or look at what other question(s) you could ask in its place.

If you find yourself knowing everything there is to know about the work or landscape around your ideas, it might be that you’re just really that smart. It’s more likely, however, that you’ve led yourself astray and have naively accepted the fact that there’s nowhere else to go from where you are now.

For creativity, there is no stopping point. Questions are the guiding points that help us explore where to go from here.


And what comes next?

Do you fully understand the question?

One question to get you through creative slumps

Photo by Benny Lin.

And what comes next?

I think that’s a reliable question for uncovering the value of ideas: “What comes next?”

If you’re unable to answer that question realistically (six times in a row for any single idea), you should rethink the idea.

You have an idea for a new business… and what comes next? Testing the market, naming the business, seeking funding?

You realize there’s a cafe down the street perfect for hanging your paintings… and what comes next? Who would be the right person to talk to about getting the work hung? Why your work? Why that spot?

You have an idea for a novel that you think is completely unique… and what comes next? How can you validate the uniqueness? Who would hear (or, in this case, read) what you have to say?

It’s not uncommon to have an idea, think it’s the best thing in the world, and then watch it slowly melt into the recesses of your mind, never to be thought again.

Instead of lettings ideas go to waste, it’s worth spending an extra five minutes, right now to ask yourself what comes next.

You’ve got the idea, what are you going to do with it now?



When an idea strikes, act

You have to take action if you want to succeed

Photo by Duncan Hull.

What if you started with ‘what if?’


What if you wrote daily about your struggle to become a professional artist? Then published those entries as a small ebook on Amazon for $5?

Or what if you recorded a short video explaining your struggles as a budding writer? You could syndicate it to writer communities and invite them to your blog or website to follow your journey.

What if you offered to do a lecture at a nearby University on the topic of working a full-time day job while compiling avant-garde poetry into a small book at night? Then invite students to read the book for themselves and tell their friends about it.

What if, instead of complaining that you don’t have the right tools or connections to do what it is that you want to do, you took those feelings and those constraints and made something completely different? Something fast, tangible, that you could benefit from making right now?

The worst case of following-through with such “what if” scenarios is that you end up with something you can sell for money to fuel your dream, or something to giveaway and start making more of a name for yourself. The result could lead to gaining a following that might, if you’re smart, pay you to follow your dream later on.

The best case is you learn something in the process of making or doing that other thing; you find some hidden inspiration or motivation and get back onto the path of doing what you wanted to do in the first place.

But you can’t simply ask “What if?” all the time. You have to follow through, or at least try to.

You’ll find, I think, that most of the time it doesn’t matter what types of “What if” questions you’re asking. All that matters is that you are asking them as you go, and that you’re following through with answers. This natural curiosity and experimentation often leads to creative insights. You benefit.

Start with ”what if.“