Much of an executive’s workday is spent asking others for information—requesting status updates from a team leader, for example, or questioning a counterpart in a tense negotiation. Yet unlike professionals such as litigators, journalists, and doctors, who are taught how to ask questions as an essential part of their training, few executives think of questioning as a skill that can be honed—or consider how their own answers to questions could make conversations more productive.

That’s a missed opportunity. Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.

For some people, questioning comes easily. Their natural inquisitiveness, emotional intelligence, and ability to read people put the ideal question on the tip of their tongue. But most of us don’t ask enough questions, nor do we pose our inquiries in an optimal way.

The good news is that by asking questions, we naturally improve our emotional intelligence, which in turn makes us better questioners—a virtuous cycle. In this article, we draw on insights from behavioral science research to explore how the way we frame questions and choose to answer our counterparts can influence the outcome of conversations. We offer guidance for choosing the best type, tone, sequence, and framing of questions and for deciding what and how much information to share to reap the most benefit from our interactions, not just for ourselves but for our organizations.

Don’t Ask, Don’t Get

“Be a good listener,” Dale Carnegie advised in his 1936 classic How to Win Friends and Influence People. “Ask questions the other person will enjoy answering.” More than 80 years later, most people still fail to heed Carnegie’s sage advice. When one of us (Alison) began studying conversations at Harvard Business School several years ago, she quickly arrived at a foundational insight: People don’t ask enough questions. In fact, among the most common complaints people make after having a conversation, such as an interview, a first date, or a work meeting, is “I wish [s/he] had asked me more questions” and “I can’t believe [s/he] didn’t ask me any questions.”

Why do so many of us hold back? There are many reasons. People may be egocentric—eager to impress others with their own thoughts, stories, and ideas (and not even think to ask questions). Perhaps they are apathetic—they don’t care enough to ask, or they anticipate being bored by the answers they’d hear. They may be overconfident in their own knowledge and think they already know the answers (which sometimes they do, but usually not). Or perhaps they worry that they’ll ask the wrong question and be viewed as rude or incompetent. But the biggest inhibitor, in our opinion, is that most people just don’t understand how beneficial good questioning can be. If they did, they would end far fewer sentences with a period—and more with a question mark.

Dating back to the 1970s, research suggests that people have conversations to accomplish some combination of two major goals: information exchange (learning) and impression management (liking). Recent research shows that asking questions achieves both. Alison and Harvard colleagues Karen Huang, Michael Yeomans, Julia Minson, and Francesca Gino scrutinized thousands of natural conversations among participants who were getting to know each other, either in online chats or on in-person speed dates. The researchers told some people to ask many questions (at least nine in 15 minutes) and others to ask very few (no more than four in 15 minutes). In the online chats, the people who were randomly assigned to ask many questions were better liked by their conversation partners and learned more about their partners’ interests. For example, when quizzed about their partners’ preferences for activities such as reading, cooking, and exercising, high question askers were more likely to be able to guess correctly. Among the speed daters, people were more willing to go on a second date with partners who asked more questions. In fact, asking just one more question on each date meant that participants persuaded one additional person (over the course of 20 dates) to go out with them again.