The Art of Asking Questions

The answers we get are a consequence of the questions we ask. Asking means we want to learn. Answers deepen our understanding, provide solutions to problems, improve relationships, signal competence and overcome the many fictions we tend to believe are true. Naguib Mahfouz, a Nobel laureate for literature, said you can tell a clever man by his answers and a wise man by his questions.

At the age of four, children ask over 400 questions a day. Between the ages of two and five, the average child will have asked about 40,000 “why” questions, simply because they do not know. As we age, apparently we do. By the time we reach 44, adults only ask around six questions/day, mainly because we either think we know or are afraid of admitting that we don’t.

Why don’t we ask more questions or, at least, the ones we should be asking? Maybe it’s arrogance – being more impressed with our own narratives than with the ideas of others. Perhaps it’s apathy or not caring much what others think. My classroom experiences suggest it’s a fear of asking the wrong questions and being viewed as incompetent. I tend to think the reason is that most have little understanding of the fundamentals of asking good questions and of the power that flows from ending our thoughts with a question mark rather than a period.

Much of a leader’s workday is spent asking for information. Yet, unlike litigators, journalists or doctors who are trained in framing their questions to get what is needed to do their jobs, few executives think of questioning as a critical skill. That’s a missed opportunity. CEOs concur: in a recent study, over 90% say they don’t get “real answers” to their most important questions. Some of these non or vague responses reflect an unwillingness to speak truth to power; others are a consequence of an inability to phrase questions in a manner that invites the information sought.

The art of asking questions is a tool for unlocking value: it spurs learning, fuels innovation, improves performance, mitigates risk and builds trust. Good questions stimulate strategic conversations, surface crucial assumptions, encourage curiosity, focus enquiry and generate even better questions. They engage listeners in meaningful ways. In his 1936 classic, How to Win Friends and Influence People, Dale Carnegie advised: “Ask questions the other person will enjoy answering.” More than 80 years later, most of us still fail to heed his sage advice.

As a crisis interventionist and fact-finder, the primary tactic in my investigatory arsenal was the ability to ask artful, engaging and probing questions. Without accurate information, I couldn’t do my job. Based on decades of experience, here are my suggestions for improving your questions:
•  Ask more open-ended questions. When people feel backed into yes-or-no corners, they sense they’re being interrogated. Open-ended questions deliver unexpected, insightful responses.
•  Ask follow-up questions. They signal you’re listening, that you care about them and want to know more.
•  Practice strategic silence. The best response to a partial answer is to say nothing. The second best response is to say “Anything else? … Please go on.”
•  Frame questions in an appropriate tone. People are more forthcoming when asked in a casual rather than confrontational manner. They’re more willing to respond when given an “out.” If we’re told we can change our answers whenever we want, we say more. And rephrasing questions previously asked often reveals different, if not better, answers.
•  Sequence your questions. Gradually build to what is deemed critical to the enquiry. The optimal order depends on the circumstances: in some encounters, asking tough or sensitive questions first, even when socially awkward, can generate helpful information. Discovery is a delicate balance requiring an understanding of the respondent’s state of mind and willingness to share.

The questions you ask depend on the situation as well as your objectives. As a leader, you might ask whether anyone has a perspective that differs from yours. As a parent, you could ask whether you’re asking the questions you should. As a negotiator, you want to know whether the other has told you what you need to know to make the right decision. There really are no dumb questions. Because, in life, dumb is often smart.

Healthy skepticism in an age of misinformation and post truth generates good questions. This is our defense against deliberate guile, manipulation, ambiguity and lies. Whenever possible, use enquiry to solicit independent (hence objective) verification of the “facts.” Beware self-proclaimed experts, even when their credentials say they are. Diligently look for alternative explanations and stimulate contrarian views. Compare and test your assumptions fairly against theirs. Insist on (observable and measurable) specifics rather than gross generalizations.

When framing your questions, be mindful of defensive responses that contain the most common fallacies of logic and enable the perils of rhetoric. These include (but are not limited to):
•  Attacking the arguer rather than the argument;
•  Misplaced trust in the presumed expertise of self-described authorities;
•  Appealing to ignorance, selective interpretation, circular reasoning or begging the question (assuming answers without confirming evidence);
•  Misunderstanding how statistics work, like not knowing the difference between correlation and causation;
•   False dichotomies – offering only the extremes in a continuum of possibilities, such as “Either you love your country or you hate it”); and
•  Half-truths (suppressed evidence) and weasel words or reinventing language for political purposes.

Asking questions that stimulate quality communication is like a dance; it requires the partners to be in sync. Just as how we ask questions facilitates trust and information sharing, so too can the way we answer them. The wellspring of great questions lies in an insatiable curiosity and capacity for wonder. The art of asking can be transformative. Progress depends entirely on our ability to seek out novel information. Thoughtful and timely questions, properly phrased, foster smoother interactions and lead to brilliant discoveries.

The Game of Life: A live Conversation (also available on Amazon)