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How to ask questions that get people to open up

The quickest way to learn new info is to tap into the ideas of those around you, but most people don’t ask enough questions, says this expert.

How to ask questions that get people to open up
[Source photo: Priscilla Du Preez/Unsplash]

What you don’t know can hinder your potential and growth. Unfortunately, it creates a paradox, because you don’t know what you don’t know. The quickest way to learn new information is to tap into the ideas and insights of the people around you, but people often don’t ask enough questions, says Jeff Wetzler, author of Ask: Tap into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life.

“The biggest reason is because we don’t realize the question that needs to be asked in the first place,” he says. “We size up situations so quickly and jump to conclusions. We feel that those conclusions are reality, and it doesn’t occur to us there is something we don’t know. If you feel certain about something, it’s logical that you wouldn’t ask questions.”

Another reason people hold back from asking a question is that they overestimate how the other person is going to feel about being asked, says Wetzler. “We think the other person is not going to want to be put on the spot, but research shows that people actually appreciate being asked questions to express who they are and what they’re going through.”


Few people are taught how to ask good questions. As a result, we often have a relatively narrow repertoire of questions, most of which won’t enable us to learn something important. Instead, Wetzler recommends asking high-quality questions, which signal curiosity.

“It’s not enough to inject new questions into your vocabulary if you’re not genuinely curious,” he explains. “Quality questions are clear and direct. They’re not trying to use a question to disguise a suggestion or a piece of advice.”

A quality question also creates mutual benefit. “They’re not just for the benefit of the asker but actually benefit the person being asked,” says Wetzler. “It helps them to express themselves, clarify their thinking, and really engage in relationships.”


One of the strategies for asking a high-quality question is what Wetzler calls “request reactions.” The asker says, “Here’s what I would like to do,” or, “Here’s my suggestion,” and then says, “What are your reactions to that?” or, “How does that land with you?” or, “What might I be missing?”

“You’re requesting reactions from someone,” says Wetzler. “The reason it’s so powerful is that often when we express what we think to somebody else, we assume if they have a reaction—positive or negative—that they’re going to tell us. If they don’t, we assume that they must have agreed.”

But that’s not always true. For a variety of reasons, people often don’t feel safe sharing real reactions. If you pose the question, however, it radically increases the chances that you will understand what they have to say.

Another technique is what Wetzler calls the “clear up confusion strategy.” When someone makes a statement, you may think you know what they mean. Sometimes, though, you don’t. Wetzler suggests asking, “When you said X, what did you mean by that?” Or, “How would you define X?”

“So many conversations would go so much better if we just took the time to clarify,” he says.

A third strategy is what Wetzler calls “callback and test.” Before you react to what someone says, paraphrase what you heard back to them. For example, “Here’s what I think I heard you say. Did I get that right?”

“When I do this, at least 50% of the time the other person says, ‘Well, you kind of got it, but that’s not exactly what I meant,’” says Wetzler.“ Or, ‘Yes, you got it. But there’s another thing I forgot to say.’”

The callback and test strategy not only helps you get more information; it slows down the conversation, which can be helpful if things are getting tense. It sends a message to the other person that you care and want to understand what they have to say because you’ve taken the time to put it in your own words, says Wetzler.


While asking the right questions is the first step, it’s also important to make answering truthfully safe for the person being asked. This is done by lowering the barriers so it’s more comfortable and appealing for someone to tell you the truth.

For example, if you’re a CEO, don’t invite someone into your office, sit across your desk from them, and assume that they’re going to feel comfortable. “Go to where they are,” says Wetzler. “Eat lunch with them. Ride in the car together. Take a walk. Go wherever they’re going to feel most comfortable.”

Make it clear why you’re asking the question, so the other person doesn’t have to guess your agenda. And radiate resilience, letting the person know that you can handle their truth. Wetzler says it’s important to be clear that you won’t get defensive or take it out on them. For example, create safety by saying, “Listen, if I were in your shoes, I would probably feel very frustrated right now. If that’s what you’re going through, I would love to hear about it.”


Question-asking is like any other skill. It takes practice, but the benefits are worth it. Start by becoming aware that you’re probably not naturally doing it. Wetzler recommends recording conversations and looking at the transcripts. Compare how many questions you ask to how many statements you make.

“It’s often shocking,” he says. “People are often surprised that they asked no questions, or one question that was more like an attack question.”

Then make a conscious effort to try high-quality question techniques. “As you practice more and more, and you see what works and what doesn’t,” says Wetzler. “Over time, it becomes second nature. You start to push aside thoughts like ‘Do I look good at this conversation?’ and center on the intention of ‘What can I learn from this person?’”

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