The art of asking questions

A version of this article originally appeared in Quartz’s Leadership newsletter. Sign up here to get the latest leadership news and insights straight to your inbox.

Children ask a lot of questions — sometimes several hundred per day, researchers estimate and exhausted parents of preschoolers can confirm.

That’s when curiosity peaks for most humans. Back when we’re still firmly in rugrat party USA mode, asking things like whether we can grow up to be our favorite dinosaur, or whether we need to fear a tree growing in our bellies if we eat any seeds.

Question-asking increasingly tapers off through our school years. It seems to be the societal pattern. Outliers aside, most school systems prioritize answers and compliance over curiosity.

By adulthood, we’ve learned that asking too many “why” or “what if” questions at work risks slowing down projects, annoying our bosses, or exposing our ignorance.

This absence of curiosity leads to increased conflict between individuals and groups with divergent points of view. It yields more loneliness and shallower connections in our interpersonal relationships. And it results in less-than-optimum business outcomes in terms of both culture and bottom-line results.

What can asking better questions do for you and your business?

Author and speaker Warren Berger is among the world’s thought leaders on the subject of questions. Berger has written several books, among them the bestseller “A More Beautiful Question,” and its follow-up, “The Book of Beautiful Questions.”

In a recent interview, Berger talked with us about what tends to stop business leaders from both asking questions and being open to receiving them in the workplace — and about some of the consequences of doing things that way.

“It’s tied to the idea that questioning represents weakness for them,” Berger said. “Because if you question, in their mind, it means you don’t know. And that means, why don’t you know? Aren’t you supposed to be the leader? Aren’t you supposed to be the expert?”

And if someone else is asking them questions, they may see it as challenging their authority, he said.

“So they’ve got a double problem with it,” Berger said. “They’ve got a problem with themselves asking questions because it shows vulnerability, and they’ve got a problem with other people asking them questions because they see it as challenging their authority, or possibly putting them on the spot.”

Leaders need to have a balance between confidence and humility, he said.

“The humility part is, you’re going to be a questioning leader. It means you have to admit that you don’t have all of the answers,” he said. “But you must be confident enough that you can be vulnerable and people will still follow you. That they’ll still think you’re a leader even if you don’t have all of the answers.”

Doing this is ‘completely wrong,’ questionologist says

“One of the most common things that leaders do around questioning that’s really bad,” Berger said, “is that they’ll say, ‘Don’t come to me with problems, or questions, or whatever unless you can answer it.’

“It’s completely wrong.”

When someone has a question, they don’t typically have the answer at that time. 

To inspire and unlock creativity, use ‘how might we?’ questions

“I like ‘How might we?’ questions. They’ve proven to be very effective over the years,” Berger said. “Instead of saying ‘What should we do?’ or ‘How should we do it?,’ you’re asking ‘How might we? How might we find a way?’”

For example, instead of mission statements, individuals and organizations might consider mission questions.

“So, you know, our team needs to do a better job of making this part efficient, while also making sure the customer’s satisfied with that,” Berger said. “You phrase that as a big ‘How might we?’ question.

“How might we find a way to improve this part of the process while at the same time making sure we address X, and also doing a better job at Y?”

Berger literally recommends putting that in a big, multi-part, ‘How might we?’ question.

“I like those kind of big, complicated ‘How might we?’ questions, because what they’re saying is, ‘Problems are complicated. Challenges are complicated. There’s usually three or four things you’re trying to do at the same time,’” Berger said. “So let’s put all that into a question. Let’s make sure the question addresses A, B, and C as all part of the same question, and once we do that, it’ll be a really good question. It’ll be a question that addresses the entire problem — the entire challenge that we’re trying to solve.”

On tone and intentions

There’s more to effective question-asking than simply organizing words in the best way, Berger said.

“I can ask the same question, and just by shifting the tone a little bit, I can change it from a question that inspires thinking to one that shuts everything down,” he said.

As an example, Berger offered the question: “Why are you guys doing it that way?”

You can say it with a tone that shuts people down, and implies that the team was foolish to do something the way that they did. Or, shift from a critical tone to one of authentic curiosity that basically says “I’m wondering why are you using that particular approach?”

Beware of ‘counterfeit’ questions

“So your questions should have that element of curiosity in them, and if they don’t, then it means you’re just using it as a rhetorical tool to either criticize people, or to show off, or to whatever,” Berger said. “I call that counterfeit questioning.”

The key to asking questions, he said, is that they should be rooted in authentic curiosity.

Shifting toward a more curious work culture

Like all healthy relationships, the No. 1 factor is trust.

“If you’re trying to shift your culture toward a more questioning culture, there has to be a shift toward more trust,” he said.

You’re asking people to trust that it’s OK for them to ask questions. 

“In a culture where there is no trust, there won’t be questions,” Berger said. “You can’t do it in cultures that have a bad leader. You can’t do it in cultures that have no trust. It’ll never happen if it’s an unsafe culture.”