Curiosity Ignited: Mastering Effective Questioning Techniques

Hugh Schulze
15 min read

Questioning techniques and curiosity are two powerful tools in the arsenal of anyone seeking to gain deeper insights and understanding. Effective questioning techniques are essential for unlocking knowledge and encouraging creative thinking, while curiosity is the driving force behind the desire to learn and explore. When used together, they can lead to breakthroughs and innovative solutions to problems.

At one of my first copywriting jobs, I met a man I came to call “Not Enough Bob.” N.E.B. was a senior copywriter in his late thirties/early forties. At the start of each workday, you could find him at the coffeemaker, mug in hand, shaking his head. Ask him what was wrong and he would tell you about the latest ad or brochure he was writing. “I don’t know what they expect,” he would lament. “There’s not enough information.”

As I would come to learn, this was Not Enough Bob’s way of avoiding putting fingers to the keyboard and procrastinating, the same way a copywriter today might fire up a YouTube video or listen to a WTF podcast.

Which is not to say that information can sometimes be in short supply or muddled up in business-speak that seems more interested in camouflaging inadequacies, such as a lack of differentiation from a competitor or lack of understanding of the target audience. Sometimes you will need to do the heavy lifting to get beyond a hundred product features before you find a single, real customer benefit.

But there is an important – and potentially creative – tension between what the client knows and what the agency needs to know to successfully do their job. “Do I have to write the [ad/brochure/script/fill-in-the-blank] myself?” the over-interrogated client might rightly ask. The question, of course, is not how many questions you ask but asking the right ones. The right ones are the ones that provide an insight that can lean to a strong concept that can lead to successful communication.

“Unask the Question”

Listening to a recent podcast, I was reminded of a passage from Robert Pirsig’s Zen and the Art of Motorcycle Maintenance.

Yes and no… this or that… one or zero. On the basis of this elementary two-term discrimination, all human knowledge is built up. The demonstration of this is the computer memory which stores all its knowledge in the form of binary information. It contains ones and zeroes, that’s all.
Because we’re accustomed to it, we don’t usually see that there’s a third possible logical term equal to yes and no which is capable of expanding our understanding in an unrecognized direction. We don’t even have a term for it, so I’ll have to use the Japanese Mū. Mū means ‘no thing.’ Like ‘Quality’ it points outside the process of dualistic discrimination.
Mū simply says, ‘No class; not one, not zero, not yes, not no.’ It states that the context of the question is such that a yes or a no answer is in error and should not be given. ‘Unask the question’ is what it says.
Mū becomes appropriate when the context of the question becomes too small for the truth of the answer. When the Zen monk Joshu was asked whether a dog had a Buddha nature, he said ‘Mū,’ meaning that if he answered either way he was answering incorrectly. The Buddha nature cannot be captured by yes or no questions.”
—Zen and the Art of Motorcycle Maintenance

Zen koans may seem a somewhat paradoxical way of addressing questions – but I think the passage as a whole speaks of one of the unique biases in asking a question: we can often presume an answer. Are we genuinely interested in gaining an insight? Or are we, like my colleague, Not Enough Bob, simply questioning for the sake of asking questions?\

In an earlier blog post, I wrote about the power of curiosity. One of the opportunities we have as the question-askers is to engage our subjects in unexpected ways; at the risk of over-stating the case, it can become more of a shared game of inquiry. I’ve asked CEOs to describe their companies as if describing a person. The range of answers is surprising and better yet, more engaging.

The best questions are the ones that make your subject search for the answer – not parrot a fact. Here are three ways for approaching questions in a way that uncovers hidden value.

The Question Burst

If you think of great places where questions are asked, you’d be hard pressed to find a better place than MIT. Hal Gregersen, executive director of the MIT Leadership Center, has written a book: Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life.

One of Gregersen’s recommendations for business leaders is to try a kind of brainstorming he calls a “Question Burst.” A central challenge or opportunity is presented to a group and each person is asked to write down “how they feel about it.”

Then for a period of four minutes, everyone takes turns asking questions about the challenge or opportunity. With two rules: a) no one is allowed to give answers; or b) explain why they are asking the question (Mū!). “This way,” Gregersen says, “You’re not restraining the way other people see the problem or opportunity.”

At the end of four minutes, each person is asked to do another emotional check to see who may feel different. Then the group jointly examines the questions and decides which deserve more research.

According to Gregersen: “At least 80 percent of the time the challenge is slightly reframed in a better way, and at least one valuable new idea is generated. Not only does the process generate more ideas than simply proposing solutions, it produces motivational benefits.”

D’Arcy Ryan, senior vice president at Edelman, has worked on both the client and agency sides of the table. As she works with a client in discovery: “I think the answer to the question, ‘What is your most important problem to solve?’ can be incredibly helpful. Especially as you start digging deeper: Is that really your problem? Or is the problem that a senior executive thinks that’s the problem. This requires going deeper and deeper: is that really the most important problem?”

Four Types of Questions

In an article for Harvard Business Review, Alison Wood Brooks and Leslie K. John explore research done using human coding and machine learning. In natural conversation, they identify four types of questions: introductory questions (“How are you?”), mirror questions (“I’m fine. How are you?”), full switch questions (ones that change the topic entirely), and follow-up questions.

Although each type is abundant in natural conversation, follow-up questions seem to have a special power. They signal to your conversation partner that you are listening, care and want to know more. People interacting with a partner who asks lots of follow-up questions then feel respected and heard.”
—Alison Wood Brooks and Leslie K. John, The Surprising Power of Questions

Effective follow-up questions require a skill that virtually every article or TED Talk on the subject emphasizes: active listening. Active listening helps you avoid the trap of simply confirming your own assumptions and asking questions that do the same. It encourages a deeper understanding of the subject and can lead to the kind of insights essential for creating concepts that are both unique and engaging, concepts with the element of surprise for your target audience.

The Five Whys

Author Charles Duhigg has written about the Toyota Production System and its use of The Five Whys as “a process of continually asking questions until you get to the root cause.” Implicit in this approach is the idea that often our first answer to “Why?” lies closest to the surface of what is a deeper, underlying idea or cause. The discipline of asking five “Whys” imposes a kind of “Yes, and….?”, which is at the heart of any good brainstorming.

The Five Whys method has helped managers eliminate waste, helped children understand how to analyze problems and find solutions and assisted teachers in creating environments where even underperforming students can succeed.
At the center of the Five Whys – and the reason it’s so effective – is a basic insight: ‘Productivity’ means different things to different people, but at its core, it’s about thinking a little more deeply about the choices we make every day.”
—Charles Duhigg

At c|change we’ve used this methodology to address internal processes and what we need to do to get to the root cause of them. Applying them to the creation of Creative Briefs for clients can be an eye-opening experience, depending on the topic. But it’s one that needs to be applied carefully (with lots of explanation) lest you start sounding like a petulant four-year-old.

A Concept is a Box of Questions

In closing, let’s revisit why we’re asking these questions in the first place. We certainly need enough information, but the kind of insights that will help us do our best work is different from the factoids which Bob was half-heartedly searching for.
Ultimately, at c|change, our job is to help our clients engage their customers and prospects in a dialogue about their product, solution or service with the goal of deepening that dialogue and relationship.

In presenting our creative solution – whether that is a strategic communication plan or a video script, a website or a tradeshow booth – we see our initial concepts as opportunities for dialogue. Often we’ll present multiple concepts – with rationale – to show how much a concept can change when the emphasis is shifted even a little bit.

Our best clients are the ones who see this opportunity for dialogue as a way of getting beyond “Right and Wrong,” “Yes and No” and moving us to something that may have an authentic emotional quality, a kind of hard-to-define sense of connection, that you might just call: .

Coda: Unanswered Questions

Not long after I turned 40, I was in the basement of my parents’ house and came across an old paperback edition of Robert Pirsig’s Zen and the Art of Motorcycle Maintenance. When I began flipping through the pages I found notes and marginalia written in pencil by my father. Reading his notes I was intrigued at how they gave me an insight into his thought process. Here were ideas that had engaged him though I wasn’t quite sure if he always agreed with them or if he was calling them out to be challenged.

I saw this as an opportunity to learn a little more about him, so I snuck the book into my backpack and returned to Chicago. I then wrote my father a lengthy letter in which I quoted one of the passages he had highlighted and asked him some questions about the passage.

My father was not a religious man. And after a working lifetime in which he read a great deal of non-fiction, in his retirement he took some adult-ed courses such as Introduction to Philosophy. But I had never engaged him in a dialogue of what he did or did not believe. I saw this as my opportunity.

But after posting the letter with my questions, I never received a reply. I vaguely recall asking him if he had received the letter and think he said something like: “I have to think about it. A lot of questions.”

At this funeral a few years ago, I related this failed experiment to a friend. At the time, it felt like a missed opportunity to know him a little bit better. “Sometimes there are questions we don’t know the answers to,” my friend said. “And sometimes there are questions we don’t want to know the answers to.” Only then did I realize the presumption of my questions.

It reminded me of the need for humility, generosity and permission necessary before asking any question. While one might think a tremendous gulf exists between curiosity and interrogation, to the person being asked the question, it can be a very fine line.

In today's fast-paced and constantly changing world, it's more important than ever to develop effective questioning techniques and nurture a sense of curiosity. By asking the right questions and actively seeking out new knowledge, we can uncover insights and opportunities that were previously hidden. With the power of curiosity and effective questioning techniques, we can approach problems with a fresh perspective and unlock new possibilities for growth and success.