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The Most Successful People in the World Ask Questions Constantly. Here's How to Master the Art of Asking Questions

Don't stress about your blind spots – use them to get better.

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"The art of proposing a question must be held of higher value than solving it.” 

—Georg Cantor

We ask questions all the time. When is the presentation? Did you get my notes from the meeting? These are straightforward, fact-finding questions, and they get straight-forward, fact-based answers. (It’s at 3. Yes.) It shouldn’t be surprising that my company, JotForm, sees more than two million user questions per hour.

But a thoughtful, well-posed question has tremendous power; opening the doors to innovation, building cohesion among team members and shining light on the dark corners of misunderstanding. 

Even so, many of us still shy away from asking questions, despite how invaluable they can be. Experts offer several explanations for why this is: Some people are egocentric and more interested in sharing their own points of view. Others are overconfident, assuming they already know the answers. Then there’s the other end of the spectrum: Those who worry that they’ll ask the wrong question and be perceived as incompetent. 

“There are so many vulnerabilities surrounding this,” Warren Berger, author of A More Beautiful Question and The Book of Beautiful Questions, tells Forge. “It can really feel like questions are a dangerous thing.”

In fact, the opposite is true — the most successful people in the world ask questions constantly. If you’re not a natural question-asker, learning how can seem daunting. As the mathematician Georg Cantor points out in the quote above, asking good questions is an art. And with practice, it can be mastered. Here’s how to get started. 

Related: How to Ask the Right Question in the Right Way

Be specific 

Before you ask a question to someone else, it’s important to first figure out what you’re trying to learn. If you’re not sure, it’s unlikely that the person you’re asking will either. 

Most questions can be divided into three types: Factual, opinion or request. Each carries its own message. Asking a factual question shows that the other person has information we don’t; asking an opinion indicates we value their perspective; and making a request implies that we need help. Once you’ve gotten to the heart of what question you’re asking, consider who you’re asking, and whether they’re in the right position to answer it or not. 

As a leader, asking questions can feel like a giveaway that you don’t have all the answers. Which, obviously, you don’t. But far from projecting weakness, asking questions is actually not only a great way to gather valuable information; it shows your team that you respect and trust them. 

Related: The 4 Keys to Asking Better Questions

Don’t be afraid to clarify 

It’s often the case that asking a single question isn’t enough. Maybe the answer was overly technical; maybe you realized that you didn’t ask the precise right question after all. It happens! 

If the answer you receive leaves room for ambiguity, you’ll need to clarify. Usually, these questions are either open, in which you ask the speaker to elaborate on part of their point; or closed, in which you repeat the ambiguous part of the message back and ask for confirmation that you understood it correctly. 

When asking for clarification, make it clear you’re simply trying to understand, rather than blame the answerer for answering poorly. After all, you’re both working toward the same goal, which is to understand each other. 

Related: The Power of Asking Dumb Questions

Conversation vs. interrogation

There’s a fine line between showing your interest in what someone has to say and making them feel like they’re being bombarded. Rather than asking questions at a machine gun clip, take some time after you’re answered to consider what you just heard. Remember, it’s a conversation, not an interrogation. 

Keeping questions open-ended is a good way to avoid “yes” or “no” answers, and also allow for more creative responses. According to Alison Wood Brooks and Leslie K. John, both professors at Harvard Business School, these kinds of questions can be “wellsprings of innovation.” 

On the other hand, survey design research has shown that “closed” questions can introduce bias and manipulation — leading the witness, so to speak. In one study, in which parents were asked what they considered  “the most important thing for children to prepare them in life,” 60 percent chose “to think for themselves” from a list of possible responses. In contrast, when the same question was asked in an open-ended format, only about five percent of parents gave a response along those lines. 

Find the right tone

Different circumstances call for different modes of questioning, and how you ask a question can be just as important as what you ask. Overly direct questions that seem to come from out of the blue can make people clam up, but beating around the bush can lead to frustration on both ends. Brooks and John found that people are actually more willing to reveal sensitive information when questions are asked in a decreasing order of intrusiveness — as long as the first question isn’t too sensitive. It’s a balance. 

The same goes for context. If you’re making an important request, you’ll want to pick a time when the other person isn’t in the middle of something else or in a noisy, crowded environment. 

Keep quiet

In general, it’s a good idea not to interrupt people while they’re talking to you. This becomes even more true when they’re trying to answer a question that you asked. Interrupting sends a clear message that you don’t value what they’re saying, and also keeps you from hearing what they might have said. 

If the conversation seems to be meandering from the topic you want to focus on, gently guide it back. There’s a difference between doing this and cutting someone off mid-sentence because you had a thought of your own to add. Save your own thoughts and questions for when the answerer is done talking — then, wait a beat beyond that to make sure they’ve truly finished their thought. Sometimes that extra pause yields the most important thing a person was going to say. 

People who ask questions have higher emotional intelligence and a greater understanding of the world around them — plus, people like them more. If you become a good question asker, there’s no end to the knowledge you have the power to unlock. 

Related: Why the Best Managers Ask the Most Questions

Aytekin Tank

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Entrepreneur Leadership Network VIP

Aytekin Tank is the founder and CEO of JotForm, the easiest online form builder. JotForm was ranked in the 2016 Entrepreneur 360™ List, an annual ranking of the most entrepreneurial private companies in the U.S.