How to Ask Better Questions, According to a Leading Expert

Harvard psychologist and author Steven Pinker on how to make sure you’re asking the types of questions that will lead to your success.

Courtesy of PR Image Factory/Shutterstock
Courtesy of PR Image Factory/Shutterstock

Whether it’s at work or in other facets of life, one marker of people who find success is that they are very good about asking questions — probing questions, open-ended questions, revealing questions, the right questions. But as we all know, the art of asking questions is changing, thanks to voice platforms like Alexa and Siri and, for that matter, the particular vernacular that Google and the ensuing advent of search engine optimization has brought about. We’ve been conditioned, for the past 20 years or so, to frame our thoughts based on how other people frame theirs. Siri, what is an Italian restaurant near me? Does the prevalence of this Jeopardy-sounding, lowest-common-denominator sentence structure discourage creative thinking, a part of which is the asking of new and unexpected questions?

The well-known Harvard psychologist, author, and cognitive scientist Steven Pinker pondered the state of the union of questions-asking — and by extension, the future of human curiosity — in a conversation at the Cannes Lions advertising festival Tuesday, as he was interviewed (irony intended) by Adam Singolda, the Israeli-born founder and CEO of the programmatic advertising company Taboola.

Singolda noted that he often asks questions of his Alexa while feeding his infant son, and articulated the concern every modern parent has, which is some version of, Will my child be well-informed but a bit dull because he grows up in a world in which accessing every bit of information is as easy as browsing a Wikipedia entry or barking at a speaker? Singolda noted that Pablo Picasso was famously quoted as saying that computers “are useless” because they “can only give you the answers” but they don’t know how to ask a novel question — but Picasso made that sweeping observation made well before machine learning and Siri and A.I.

Pinker took an optimistic and reassuring approach, saying that human beings are incredibly resilient when it comes to creativity. Our ability to renew our individual (and collective) knowledge base by inventing new questions to ask is innate, he said. Every new technology medium has been met with concerns that it would dumb down humanity; worrying about screen time is not so far from fears that kids of earlier generations watched too much television or listened to too much radio, he argued. He noted that Socrates once fretted that the advent of written history was a mortal threat to intellectualism because it meant that his Athenian neighbors no longer had to maintain the sharp memories necessary to carry on the oral tradition. (Though, to be sure, many experts — including some of the folks who invented the technology — differ with Pinker’s benign view on digital screen time, and there has been scientific research suggesting an addictive quality to social media and some negative effects of too much screen time on children.)

Knowing that you’re equipped to ask the right questions is only half the battle, of course. The other half involves actually asking them. According to Pinker, there are three tips to keep in mind that will help you refine your skills of inquiry:

Ask the questions other people are not asking. This is both obvious and easier said than done. However, the hallmark of an intellectual or scientific breakthrough is that a person steps outside of what is known to ponder what gaps exist, then figures out how to fill them. If you don’t know what question people are not asking, at least make it a practice to ponder it. For instance, make it a routine to punctuate meetings or conversations with, What are we not considering?  

Ask why like a child would. Every adult has had the annoying experience of a child asking follow-up after follow-up after follow-up to a question that the adult already thought was handily answered. But it is exactly by pursuing more information incrementally, almost to the point of being a pest, that people find the edge of what is known, and therefore arrive back at the first tip, which is figuring out how to ask a question for which an answer is not known. So be that pest. Nervy kids are doing us all a favor by modeling good creativity skills.

Analogies help us to be creative, so look for them. Pinker says that one of the great gifts of the human brain is that we have a tremendous ability to make abstract connections using analogies. When we say a person went from feeling bad to being on the mend, he explains, we are instinctively comparing an illness to a journey, even though the activity of physically recuperating is not the same as physically moving from one place to another. Though a sick person recovering may not cover any ground, the analogy makes intuitive sense.

So what does this mean for you at work or in life? Well, Pinker says that creative breakthroughs in science and medicine and other fields often come when the creator stumbles upon a comparison that happens to work pretty well. One example he used is that doctors often describe how to lower a person’s blood sugar by using the analogy of lowering a thermostat. It goes without saying that a person with high blood sugar is not the same as a room that’s too warm — but as humans, we are better able to comprehend, understand, and teach the concept by using this simple analogy.

Ultimately, Pinker says that even as technology makes it ever easier to get simple answers to simple questions, we will be free to ponder and probe more complex systems and challenges. So the next time you quickly look up a fact on Wikipedia and feel faintly worried that you will forget the information as quickly as you found it, don’t worry. If Pinker is right, your critical thinking skills are not being forever compromised. Just don’t stop wondering what question you should ask next.

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