The Art of Questioning

A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change.

Warren Berger, A More Beautiful Question


In a world that is fixated on finding and knowing the right answers, the person that asks questions at school or in the workplace often come across as either ignorant or impertinent. Why? At what point did we start shutting down questions? What if we collectively took a dive into those murky waters? What might we find?

Last year, I had the pleasure of taking a deep dive into Warren Berger’s “A More Beautiful Question”; being challenged with the task of developing an onboarding course that got participants out of the answer mentality and into the discomfort of sticking with the question; and having philosophical conversations with clients at CSPS on the topic. Today, I am still mulling over the art of asking questions.

As consultants, asking questions is part of our job: at the outset of a project, we need to ask the right questions, seek varied opinions and perspectives, and understand our clients’ real needs. This practice is often formalized through the development of consultation plans, evaluation matrices, interview guides, and other tools and approaches. We do this over and over and are comfortable with the process. But what about asking the deeper questions of ourselves? What about embracing – nay, harnessing – the power of ambiguity and the vulnerability of asking questions?

Berger makes the case that an answer-based mode of work limits our capacity for innovation and is increasingly irrelevant in a society where knowledge is obsolete. To explain, while answers are readily available through a quick online search, what remains unknown to our dear Siris and Google Homes is that intangible, childlike capacity to ask questions fueled by curiosity, creativity, divergent thinking skills, imagination, and judgment. Having all of the right answers may now be a thing of the past; the new game is to be able to fully explore, probe, question, and figure out what best to do with the answers and how to ask better questions. We also need to develop the humility to question whether what we are doing is still relevant and even go so far as to challenge whether the original reasons for our practices were valid at the outset.

From the perspective that focusing on answers inhibits our ability to ask questions, expertise can become a trap. To quote Frank Lloyd Wright, “the expert is a [person] who has stopped thinking because [s]he knows.” From a young age, we teach children to recount the exact information they are told, without questioning it. Later, we value and praise those among us who develop such a deep knowledge of a subject that their expertise becomes unquestionable. The expert protects her status with postnominals, lectures, and quasi-impenetrable associations and academic bodies. She has achieved the pinnacle and no longer needs to question her knowledge set.

In reaction to these holders of truth and to the bombardment of endless information, our brains have evolved to stop questioning, dump most of what we see, quickly categorize useful tidbits, and file away the rest of the information in the long-term memory. This passive cycle of acceptance, sorting, and filing leaves no room for the imagination and for us to ask, but why are we doing this? And why in this way? And what does it all mean?

The big innovators of our society – Silicon Valley and the like – know that dealing only in answers holds us back. We sometimes see this in the more engaging and creative conferences and training sessions as well. Those who surface at the top of the market with innovative products and services have developed methods of rewiring the brain by allocating time for creativity and imagination; practicing connective creativity and thinking in reverse; “hacking” and prototyping; and embracing the Zen concept of Shoshin (the beginner’s mind). They carve out creative, unusual workspaces, reinvent Socratic conversations, and encourage employees to not only question, but also to daydream and doodle in ways that relax the mind enough to wander outside of the paradigms and rigid social norms that so heavily dominate our lives.

I have not yet been able to fully immerse myself in these exercises, but the idea of rewiring the brain interests and excites me, particularly being someone who often questions and challenges the status quo, social practices, and institutional structures and powers.

Rewiring the brain to think in questions is difficult. I begin to think of how to approach the exercise and then realize that I fall time and again into the trap of seeking a quick answer. Perhaps there is no one way of rewiring the brain and prioritizing questions. Perhaps the answer-based mode of thinking is so deeply engrained in my mind that I simply need to start relaxing into the terrifying incertitude of not even knowing how to begin. Perhaps the next time I attend a meeting, I’ll stop fearing looking silly or unknowledgeable and just embrace neoteny, asking the most genuine question I can possibly imagine. Maybe it will lead to other, more interesting questions.

I also wonder about how we might encourage questioning in our own workspaces, short of having the luxury of working in the world of hammocks and hackathons and doodling circles. Certainly, the small business world facilitates this form of questioning and prototyping for us here at GGA: we learn by doing and grow through both successes and mistakes. But moving beyond the operational, day to day questions and answers, how might we begin to feel comfortable enough to ask ourselves the scary questions? What other questions are we not yet asking? What questions are we ignoring, because we cling to the classic “way of doing things”?

What questions do you have?


Article by Eva Maxwell