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The Quest of the Question

Tips for Improving Conversations

For Richie T. Steadman, founder and a host of The Cultural Hall podcast, asking quality questions is crucial.

“If I walk into a situation where I’m not prepared with good questions, it becomes an utter waste of time,” says Steadman, who is also the producer of BYU Radio’s The Lisa Show. “If there’s no connection made between me and the other person, no one can learn or become better because of our conversations.”

Using questions to understand others, strengthen relationships, and improve oneself is a meaningful skill in any occupation. “Questions help us engage whole people—their minds, their hearts,” says Aaron Ashby, vice president of innovation at FranklinCovey Education. “A good leader spends more time with a question that provokes thinking and engages the listener rather than handing information to someone.”

Posing earnest questions forces employees to go below the surface, and that’s beneficial in any job, says Paul Godfrey, the William and Roceil Low Professor of Business Strategy at BYU Marriott.

“To solve a problem effectively, you have to make sure you’re solving the right problem, which is often two or three levels below the surface,” Godfrey says. “Questions are powerful both for getting us to the deep cause of problems and for getting us to recognize the assumptions we have used to frame the problems.”

It’s likely that examining your questioning abilities will leave you feeling uneasy. The good news? A little conscientiousness can go a long way. As with learning other skills, self-awareness, practice, and a willingness to be uncomfortable will propel you on your quest to become a better communicator.

Creating Curiosity

When it comes to asking good questions, your intent is just as important as the words you choose. “A good question comes from a place of curiosity; it is not an opinion with a question mark at the end,” says Erin Clymer Lessard, chief strategy officer and principal consultant of Lapin International and author of the book Decision Flow. “Making a statement with a question mark is not a question.”

Last year, Ashby’s 20-year-old daughter noticed statements disguised as questions in Ketanji Brown Jackson’s Supreme Court confirmation hearings. “My daughter observed that the senators weren’t asking questions to actually find out what the nominee believed—they were posturing to appease their base,” says Ashby, who earned his MBA from BYU Marriott in 2003. “That doesn’t only happen in politics; it certainly happens in business. Questions ought to be seeking to genuinely understand, not to accuse or make a point.”

Steadman says there’s a natural curiosity that exists within every person. “Being a good interviewer is taking that natural curiosity and throwing it back in the form of a question,” he says. “Sometimes that takes bravery; you don’t want to look stupid or seem like you weren’t paying attention. But sometimes you just have to put yourself on the altar of not knowing.”

For Clymer Lessard, who is also a credentialed executive coach, good questions combine this curiosity with respect and humility. “When we ask good questions, there’s a sense that we don’t have to have all the answers,” she says. “Once you start managing people, you have to shift professionally—not just show up and have all the answers. As you learn to ask better questions, it communicates that what other people are thinking is welcome and critical to doing good work.”

Sometimes very simple questions can be quite profound, Clymer Lessard continues. “If I’m a leader and I see you share a challenge with a coworker, I could fixate on those details, or I could ask, ‘What relationship do you want to have with this person?’ or ‘How are you getting in the way of the relationship you want?’ Sometimes the bombs come in the simplicity,” she says.

All Ears

Clymer Lessard says asking good questions is predicated upon good listening. “Often we’re taught—and often we’re rewarded—for listening with our next response in mind,” she says. “We think, ‘How do I sound smart in the next thing I say?’” That’s level-one listening, a term she learned at Co-Active Training Institute.

But a deeper and more meaningful way to engage is to remove the habit of thinking about our response. “Level-two listening is completely focused on the other person. It’s curious and empathetic,” she says. “Different things come into my mind as I pay attention to you and your story. When I’m present and out of my own head, then I have all kinds of good questions.”

Insightful questions help the other person consider something they are wrestling with, Clymer Lessard explains: “Good questions don’t make you the problem-solver; good questions make them the problem-solver.”

Listening thoroughly is something that Ashby focuses on as a FranklinCovey employee, particularly because of the fifth habit taught in Stephen R. Covey’s The 7 Habits of Highly Effective People: Seek first to understand, then to be understood.

“We spend a lot of time helping people in organizations think about what it looks like to really listen and not impose your autobiography and not advise or probe,” Ashby says. “Probing sounds like good questioning, but it’s not. If you’re truly seeking to understand someone else, you are just asking to clarify what they’re saying and repeating back what you hear and what they feel about what they’re saying.”

Listening is not only a skill—it’s also an attitude, says Ashby. “The attitude is ‘I’m going to put my own agenda on hold long enough to understand you or to understand this situation,’” he explains. “If someone has taken the time to craft an honest, thoughtful response, you respect that.”

Savor the Silence

A conversational pause might feel clumsy, but using silence is a skill the keenest questioners possess.

“We are so prone to fill the silence because we’re uncomfortable,” says Clymer Lessard. “People need to know you’re not going to fill the space, so they can. We’re so conditioned to go fast that we’re deeply uncomfortable with silence, even a second, but sometimes that’s precisely what you need.”

Even if a few seconds feel unbearable, try to extend that time even longer. “Some of the best responses come if you let a question sit there for 10 to 20 seconds,” Ashby says. “The brain needs time to process.”

One of the things that belies honesty is asking a question and then continuing to talk, Godfrey points out: “The key to open communication is that you actually want the answer you’re asking for and are willing to wait for it.”

Authenticity is often the reward for awkwardness. “It’s perfectly fine to ask a question directly and let it sit. That allows people to finish their statements or answer the question,” Steadman says. “You will get a more authentic response because people will continue to speak. Keep waiting, and then they think of even more.”

Ask Openly and Ye Shall Receive

If leaders want answers that will help their organizations grow, encouraging a culture in which employees can speak without qualms—not just say what they think they should—is paramount.

“The proof has to come before the question,” Clymer Lessard says. “Create an environment in which psychological safety is prevalent. Make it okay for an answer to disagree with you.”

Responses and actions need to demonstrate that answering openly is invited, she continues: “You want those you’re talking with to be able to answer in a way you wouldn’t have thought of as a leader. Make space for that.”

Steadman believes demeanor is key. “I want to react in a way that’s open and not judgmental, so people know they can trust me,” he says. “I make sure my body language is not closed off.”

Approaching questions from a place of flexibility is also helpful. “There’s an element of allowing an answer to change. This conversation doesn’t have to be so final that someone is scared to answer. Try instead ‘What’s your best guess right now?’” Ashby suggests.

Of course, questioning can be challenging for people who are trying to establish credibility early in their careers. “When people are expected to demonstrate their competence, it can be hard to figure out how to use the right type of questioning,” Clymer Lessard says. When in doubt, she recommends taking a humble, teachable approach. “You could say, ‘I’m seeing it from this perspective. What else should I be considering?’ That demonstrates a teachability. Share what you see and hold it with humility. Invite rather than defend,” she says.

Steadman, who has worked in broadcasting for more than 20 years, says he hasn’t always felt like a good questioner. “I would get nervous, thinking the interview had to go a certain way,” he says. “But I learned you can’t control things, which is the best because you can get into a conversation and think it’s one thing and then have it be completely different. Sincere answers let you see things differently.”

Improving Inquiries

Some people seem naturally more inquisitive than others, which begs the question: How can someone who’s less inclined to inquire learn to do so?

“You’re limiting the value you add if you can’t find a way to be inquisitive,” Clymer Lessard says. “Find a place to start where the stakes aren’t high. It’s a powerful tool to bring into your home life. How can I be more curious when my child tells me about his day? How can I respond when listening about my spouse’s day and not dive into talking about my work?”

To help someone who might not feel naturally inquisitive, Clymer Lessard suggests, for example, doing a mindfulness exercise, which entails focusing on five things you see, four things you feel, three things you hear, two things you smell, and one thing you taste. “An exercise like this engages us in being super present. For leaders, it’s stopping the ticker tape in their heads and getting in touch with different ways of noticing,” she explains.

Few people are born good questioners, Godfrey notes. “We get trained to believe that question-asking is some magical skill, but all we need to do is practice,” he says. “One of the things we all learned as little kids was that some of the questions we really wanted the answers to, adults didn’t want to talk about. Very early on we’re told, ‘Don’t ask that’ or ‘How could you wonder about that?’ As kids we pick up quickly what’s out of bounds, and we retreat. Some of us retreat even further and stop asking altogether.”

If the thought of asking questions still gets you queasy, here are a couple of tips. “I’ll introduce myself to someone, and then I’ll ask about something in their office or their Zoom background, like a book or a picture,” Steadman says. “That leads to questions like ‘Is that a photo of your family?’ ‘Why did you choose the starship Enterprise for your virtual background?’ Many people get right to the business of a meeting, but I want to know the whole person.”

Godfrey’s favorite icebreaker question is “Where’s your hometown?” “Everybody likes to talk about where they grew up,” he says. “Once I know where they’re from, I can ask follow-up questions about sports or something else that is tied to that place. For example, if someone is from New York City, then my next question might be ‘Are you a Yankees fan or a Mets fan?’”

In addition, open-ended queries are often praised—and rightfully so. But Godfrey says close-ended questions, or those with short, simple answers, also have their place and are particularly helpful in moving things forward.

“In business you have to get to a point: Should we do this—yes or no? Is this a good product—yes or no? Those questions are helpful in getting to a decision and in implementation,” he explains. “Some questions open up discussions; others bring them to conclusions successfully.”

Avoiding Pitfalls

Sometimes questioning goes awry. One snag is asking too many questions. Godfrey believes that one way you can avoid excessive questioning is to ask, “How will the answer help me?” “If the answer doesn’t change anything, then stop asking questions,” he says.

In addition to overasking, there are other ways questions can backfire: they can highlight insecurities or be used as an ego play, Godfrey says. “What we know from sales and marketing is that whoever asks the questions is in control of the conversation. Some people don’t want to give up asking questions because they don’t want to give up control,” he explains.

For Godfrey, the questions that are most likely to flop are rhetorical ones that put people in a box. “You don’t want to use questioning to create superiority over other people or to demean them,” he says.

Additionally, asking questions for the sake of asking questions is simply a waste of time. “If action needs to happen and there’s a predetermined answer, it’s not the time to ask questions. That’s not the moment to lead employees through a discovery process,” Clymer Lessard says. “There’s nothing more annoying.”

Inquiring Minds

Some people avoid posing questions. Others offer trick questions. No doubt the quest of effective questioning boasts numerous pitfalls. Not every inquiry will elicit the conversations you hoped, and sometimes the responses might even unveil information you didn’t want to hear. But when questions create a beneficial result, the journey proves worthwhile.

“You get a better picture of the truth when a lot of people share different angles and are willing to listen to each other on how those angles fit together,” says Ashby. “Sometimes people have relevant experiences or deep thoughts that you didn’t expect. Honor the process of getting answers from everyone.”

That effort is worth the reward both professionally and personally. Like Clymer Lessard says, “It feels pretty great to be asked a question that you’re excited to answer.”


Written by Emily Edmonds
Illustrations by Eran Mendel

About the Author
Emily Edmonds is a former editor of Marriott Alumni Magazine and earned her BA and MA in communications from BYU. Her three young daughters ask her approximately 1,317 questions each day.


Four Questions from the Strategy Major

Five years ago, BYU Marriott’s Strategy Department began focusing its teaching on four questions that every business needs to ask:





Where do we compete?Why do we win with customers?How do we create value for customers?Why can’t other people copy us?

“We always thought about strategy as a very linear process, but these questions make students think in a more integrated, holistic way,” Godfrey says. “We use better questions to get better answers.”

It’s a powerful framework, he continues: “These questions simplify a whole bunch of analytical tools that look like they’re separate and unconnected, but those four questions show you a connection between all the different models and frameworks, so they allow you to unify and simplify.”


Homework from Hal

Hal Gregersen is a senior lecturer in leadership and innovation at the MIT Sloan School of Management, but before that, he taught thousands of students during his 14 years with BYU Marriott. Gregersen is passionate about understanding and sharing the crucial role of questions. If you’re interested in diving deeper into the quest of questioning, here are a handful of resources from him.


  • “What Are You Dead Wrong About Today?” (TEDxBYU video)


  • Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life (book)


  • AFP Conversations, episode 220, “Navigating Uncertainty Through the Power of Inquiry” (podcast)
  • Dear HBR, episode 57, “Stay or Go?” (podcast)
  • Disrupt Yourself Podcast with Whitney Johnson, episode 124, “Choose Your Questions Well” (podcast)

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