Learning to Ask Better Questions

One of my students asked me last week, how do we learn to ask better questions.  Like most questions from my students this one stuck in my head for a while.  Most of us too often focus our energies on finding the ‘one correct answer’ as the pathway to being (and looking) smart, but it is the questions we ask that make us look smart and, over time, result in deep, life-long, sustainable learning.  What are the characteristics of good questions?

The listeners are impressed, broken out of their daily stupor of routine nonsense, when a question is creative, demonstrating an engage mind and imagination, a brain schooled in seeing both the taken-f0r-granted as choices (rather than given) and in making connections across topics that invite new, fresh, clear, creative perspectives and analysis.

As several of you pointed out, we can all google to find facts.  We are inundated with facts, but it is the creative question that focuses our attentions (grabs the audience, mobilizes the crowd) in ways that are disruptive and transformative, they turn facts into useful and meaningful information, breaking us out of intellectual ruts and revealing pathways to actionable knowledge we can apply to more productively thinking about some problem we want to address.

Good questions make us think. Asking good questions can make us persuasive without being argumentative.  We demonstrate a desire to hear and learn from others when we ask questions, and when these are good questions, we also impress them with our capacity to make us think, to see things in fresh ways, to (hopefully) reframe a challenge to point to creative win-win solutions.

Good questions are like treasure maps when we are lost.  When we running in circles, when the world is changing too fast for us to keep up, when we are pulling our hair out of our heads, lost in a sea of facts and bullshit and tort tales constructed by others with the intention of misleading us…we cannot stop the world from changing but we can redirect the conversation, re-channel our energies, reframe from paralysis to productivity (clear thinking, purposeful thinking and acting) by finding a good question and letting go of the soul-destroying search for ‘the right answer.’  Actively using a shift to focusing on questions-as-adventures rather than answers-as-endpoints, to turn from a self-defeating focus on quantitative output when it is a search for qualitative insight we need to carpe diem.

We should ask ourselves often, as a daily intellectual and emotional inventory, what questions have I been asking lately.  If we come up empty handed, it might be time to blow up our TVs.

There is no one way to learn anything, including how to ask better questions.  The key is that we are asking ourselves…how can I ask better questions?  What does this even mean to me anyway?

This attitude makes us seekers, curious, open to learning, listeners.  This attitude or posture or approach to living/thinking centers on creativity and imagination, not independent of facts or analysis, not left brain without right brain (not dualistic thinking), but a rediscovery of our own capacity to discern and understand the world we live in, however provisionally and, as we learn over time, to understand more and more deeply in collaboration with others. 

In this way, nurturing our ability to ask questions is like putting a marker down in our own internal conflict about what kind of person we want to become.  Do we want to become leaders in our own lives or settle into a comfortably numb existence as a normal worker-bee?   Asking good questions is a starting point, where learning starts and how it grows, both in volume and excitement.  Imagine.  Think outside the box.  Live the one life we get as an adventure, a journey designed to seize each day and deepen our understanding of the world we live in, to lead us to wisdom in our old age.

On a more basic level, we learn to ask good questions by cultivating our own natural curiosity.  Others are often impressed by good questions, because it demonstrates curiosity and an actively engaged imagination seeking to find a pathway to meaningful discovery and innovation.  This is why the first step of the scientific method is the formulation of your research question.  Stumbling here (or skipping this step entirely) is a failure of imagination and a rejection of a life of the mind.

It is my hope and intention that my students this term have already experienced my class as an ongoing demonstration of how to pull, push, prod more creative, interesting, challenging and illuminating questions out of the materials we have read and discussed.  I do this because this is how I think and live and engage in our world and I see it as my responsibility to help students learn to ask their own questions, to encourage us all to become leaders in our own life, to push back when our questions are ‘just the usual suspects,’ to help each other see hidden connections, understand how power works, and actively take ownership of our own life adventure by discovering the value of critical thinking.

We can (and do) strengthen our capacity to create better questions in a variety of ways.  When we play games well, we strategize and maneuver and engage with opponents doing the same, and this active and energetic searching for new ways of thinking about the same old problems (how to play this or that hand of Euchre or attack a zone, how to best prepare garden soil or select the best player in a draft).

We do the same at work, even in routine tasks, when we suddenly realize we were asking the wrong question and discover the perfect way to present this data in a spreadsheet or power point presentation.

If we step back and think about these everyday moments, we see that we (1) have done the work over time to become very knowledgeable about the game (rules, strategies, resources, etc) and (2) we brainstorm in our heads: Will this work?  With that? What if I tried this? Maybe I am thinking about this in entirely the wrong way, what if…?  And this process of prototyping in our heads often results in finding a better question, sparking a new way of thinking about the challenge. 

If you play cards or chess or athletics…champions do not go into these contests with one fixed right answer in their mind (or with an attitude/perspective focused on finding the ‘one right answer’), but rather with a good understanding of the game and a flexible, agile mind, ready to exploit any opportunity, even those we could not anticipate before it is game on.  Champions combine the study and concentration that results in understanding the rules of the game with an equally important capacity to create, to imagine what the worker-bee participants cannot see, and this is—in a different arena—the process of learning to ask better questions.

The reason I refer to this as learning to live and appreciate a life of the mind, is because we want to internalize this capacity to ask better question, inquire, probe, investigate, examine.  If we can do this we have added an important new tool to our intellectual tool box, preparing us to learn and succeed in any context, no matter how challenging or unfamiliar.  We are less likely to live lives of fear, afraid of the unfamiliar.  We are more likely to become effective problem solvers and community leaders.  We will laugh as deeply and as often as we weep, and both will become signs of a life well lived.

From the Harvard Business Review…

Every leader I know has at least one need in common: a need to connect honestly with others. One way to help foster improved connections is by asking good questions. Leaders who excel at asking good questions have honed an ability to cut to the heart of the manner in a way that disarms the person being interviewed and opens the door for genuine conversation.

Whether they are talking to customers, interviewing job candidates, talking to their bosses, or even questioning staff, executives need to draw people out. And so often, it is not a matter of what you ask, it is how you ask it. Here are some suggestions.

Be curious. Executives who do all the talking are those who are deaf to the needs of others. Sadly, some managers feel that being the first and last person to speak is a sign of strength. In reality, though, it's the opposite. Such behavior is closer to that of a blowhard who may be insecure in his own abilities, but is certain of one thing — his own brilliance. Such an attitude cuts off information at its source, from the very people — employees, customers, vendors — whom you should trust the most. Being curious is essential to asking good questions.

Be open-ended. Leaders should ask questions that get people to reveal not simply what happened, but also what they were thinking. Open-ended questions prevent you from making judgments based on assumptions, and can elicit some surprising answers. In his autobiography, talk show host Larry King recalls asking Martin Luther King, who had just been arrested for seeking to integrate a hotel in Florida, what he wanted. To which King replied, "My dignity." Using what, how and why questions encourages dialogue.

Be engaged. When you ask questions, act like you care. Yes, act — show that you are interested with affirmative facial expressions and engaged body language. This sets up further conversation and gets the individual to reveal information that could be important. For example, if you are interviewing a job candidate you want to encourage him or her to talk about not only accomplishments but also setbacks. An interested interviewer will get the person to talk in depth about how he or she rebounded from failure. That trait is worthy of consideration in recruiting. But interviewees will only open open up — especially on sensitive subjects — if you actively show interest.

Dig deeper. So often executives make the mistake of assuming all is well if they are not hearing bad news. Big mistake. It may mean employees are afraid to offer up anything but good news, even if it means stonewalling. So when information surfaces in your dialogue, dig for details without straying into recrimination. Get the whole story. Remember, problems on your team are, first and foremost, your problems.

Not every conversation need be on point and under the gun. There will be times when you'll need a more solicitous tone and a more leisurely pace, especially when coaching an employee or listening carefully to a customer concern. There, taking your time might be most appropriate.

Asking good questions, and doing so in spirit of honest information gathering and eventual collaboration, is good practice for leaders. It cultivates an environment where employees feel comfortable discussing issues that affect both their performance and that of the team. And that, in turn, creates a foundation for deepening levels of trust.

John Baldoni is a leadership consultant, coach, and speaker. He is the author of eight books, including Lead Your Boss, The Subtle Art of Managing Up.