The counterintuitive tricks to asking better questions, according to Harvard research

Be shrewd.
Be shrewd.
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Having the ability to ask a question appears to be a uniquely human trait, one that saves us time and energy as we gather resources and information. It also allows us to develop empathy for others and create bonds of trust, even among strangers. Indeed, people who ask more questions are seen as more likable.

And yet many of us don’t ask enough questions, nor the right ones, according to research from Harvard Business School.

Writing in the latest issue of Harvard Business Review, HBS assistant professor Alison Wood Brooks and HBS associate professor Leslie John, who both study negotiations and organizational behavior, argue that we hold back our queries too often, fearful that we’ll seem ill-informed or offensive, or perhaps believing we already have the answers we need.

Whatever the reason, we need to get over it. Asking questions, even when it feels disagreeable, offers serious benefits.

“It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members,” the researchers write. “And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.”

Citing their own studies and previous academic findings from elsewhere, they offered a few counterintuitive guidelines for how to make your questions more effective.

Sometimes “closed” questions work best

We’re often told that open-ended questions keep conversations flowing, where closed questions route to dead ends, but Brooks and John make a useful distinction about when that’s true.

They say we need to assess whether an interaction is more “competitive,” which is when at least one person has an agenda or is probing for sensitive information, or “cooperative,” when two or more people are brainstorming, for instance.

When you’re dealing with a dodgy vendor from whom you’re seeking full disclosure, your conversation is competitive. In this case, the sage advice to ask open-ended questions doesn’t apply. Instead, it can open the door to lies by omission.

During a recent HBR IdeaCast podcast, Brooks offered the example of buying a used iPod to illustrate her point. Consider the open-ended “Tell me about the history of this iPod” to “Has this iPod been damaged?”

Cooperative conversations, on the other hand, really will flow most easily with open-ended questions, which give someone “a long leash” to decide “how am I going to answer this?” said Brooks. They help you discover what’s on a person’s mind.

Negative framing can lead to a positive outcome

If you have an inkling that the answer to one of your queries is going to be negative —a deliverable is going to be late, for instance—the professors suggest framing your question pessimistically. Say, “That’s not going to be on time, is it?” Your assumption gives the other person permission to be truthful, if indeed the answer is not the one you want to hear.

As with all of these questions, tone matters. Try not to telegraph anger or an accusation if you want a candid response.

Follow-up questions are “almost always” smart

If you’re not conscious about your conversational habits, you might be doing follow-up questions all wrong. That is, you might be beading together “full-switch” questions, as the professors have labeled them, which limits a conversation’s range.

“I might say things like, ‘Where are you from?’ Listen, listen, listen, listen. ‘Do you like the band U2?’ Listen, listen, listen, listen,” Brooks says on the podcast. “It would be much more engaging and interesting to say, ‘Where are you from? … Oh, I’ve been to Tuscaloosa. Do you live in this neighborhood? … I had a friend who was from there. Where, you know, where did you grow up? What were your parents like? What did your house look like? What do you regret about growing up there?'”

Follow-up questions should stay on one topic and explore it a bit, pushing the conversation past the superficial. These questions are powerful, and even “magical,” Brooks and John write, because they help the listener feel “respected and heard,” all but guaranteeing a more meaningful exchange.

Difficult conversations should launch with tough questions 

You might intuit that a sensitive conversation should start on a light note. But John’s recent research shows that your conversation partner will respond with more disclosure if you come out of the gate with hard-driving queries.

In a study published in the Journal of Consumer Research, she and her co-authors found “people are more willing to reveal sensitive information when questions are asked in a decreasing order of intrusiveness,” the professors write, because subsequent sensitive questions will feel relatively less prying. For example, they write, lead with, “Have you ever had a fantasy of doing something terrible to someone?” and then “Have you ever called in sick to work when you were perfectly healthy?” becomes way less intimidating.

But when you want to build a relationship, reverse this tactic, they are careful to add, citing “classic” research by psychologist Arthur Aron. In lab studies, he found that conversation partners grew to like each other as they asked and answered a series of questions that started breezily, with overtures like, “Given the choice of anyone in the world, whom would you want as a dinner guest?,” and move to ones such as, “Of all the people in your family, whose death would you find most disturbing? Why?”

If these questions feel familiar to you, it may be because you’ve asked or answered them not long ago. In 2015, the New York Times published the list in viral story headlined, “The 36 Questions That Lead to Love.” 

You truly cannot know where a well-considered question will take you.