Teaching Business Students to Ask Better Questions

Great managers ask great questions. That’s why strengthening students’ questioning skills should be an essential part of every business school’s core curriculum.
Teaching Business Students to Ask Better Questions

THROUGHOUT MY BUSINESS CAREER, I have never been one to shy away from asking questions. Even so, I often would leave meetings wondering if I’d missed opportunities to gain insights. Perhaps I had asked a “yes-or-no” question instead of a more open-ended one that elicited the complex reasons behind someone’s success or failure. Perhaps I had expressed my opinion prior to asking for someone else’s view. I might have posed a double-barreled question, which involved two issues but left room for only one answer, which elicited a response to a question I hadn’t intended to ask. Or, worse yet, maybe I hadn’t asked questions at all, but instead rattled off statements and expected others to somehow reply.

In short, I wasn’t asking good questions—but I wanted to learn how. To my surprise, I found that many of my colleagues felt the same. That’s when I knew that managers should be more prepared to engage others more effectively with great questions.

Since then I’ve come to view questioning as an essential business skill. According to the “2015/16 QS TopMBA.com Jobs & Salary Trends” report, employers place communication and interpersonal skills above academic achievement. McKinsey & Company predicts that interactions in the future workplace will require “a higher level of judgment, involving ambiguity, and [draw] on tacit, or experiential, knowledge in exchanges with coworkers, customers, and suppliers.” Individuals who ask great questions are well on their way to developing strong communication skills, great interpersonal skills, and high levels of judgment. They have one of the traits that distinguishes good managers from great leaders.

If that’s the case, why don’t more business schools teach questioning in their core courses? Business faculty typically view questioning skills as the domain of journalists, therapists, and detectives, or they view them as skills best learned on the job, not taught in the classroom. But when business students learn to ask great questions, they spark innovation, develop their technical skills, gather insights, and build rapport with others. I believe that their questioning competency ultimately determines how well they will succeed in their careers. That’s why students must master this so-called “soft skill”—I call it “the unquestionable management skill”—as part of their MBA core courses.


As I began exploring questioning skills, I discovered ESPN’s unique interviewing approach. In 2004, ESPN hired Canadian investigative reporter John Sawatsky to train its on-air talent to adopt a style of questioning that was different from the prosecutorial style adopted by other well-known interviewers. Today, the American Journalism Review describes Sawatsky as a “leading authority on the art of the interview,” and he has been credited with transforming journalists’ careers.

In 2010, when I approached Sawatsky about applying his method to management, he not only gave me free access to his three-day interview workshop at the network’s headquarters in Bristol, Connecticut, but also granted me permission to create a program based on his interviewing fundamentals. In that program, students first deconstruct good and bad interviews conducted by today’s reporters; then they hone their own skills through completing exercises and reading case studies based on the latest research in social psychology and cognitive neuroscience.

At the heart of Sawatsky’s method is the ability to create question sequences that uncover and explore “change points” in people’s lives, rather than focus on predictable questions about job titles, accomplishments, and company milestones. Change points are those spaces between the bullets on someone’s résumé or the items on the meeting agenda.

To be more successful in their future careers, students, too, should learn to ask questions that explore change points more effectively. For instance, account managers can use change-point question sequences to help them detect and address problems among clients and co-workers, so they won’t have to “fight fires” after the fact. Finance managers can create sequences that help them gather better internal data, make more accurate projections, and determine if their direct reports are adhering to sound accounting practices. International negotiators might create sequences that will help them gain insights about the politics, commercial risk, infrastructure, and security within their counterparts’ countries. Managers across the enterprise can craft skilled question sequences to gather information they need to write winning sales proposals, recruit star employees, retain problematic accounts, or discover market intelligence that leads to a disruptive product or service.

Faculty can help students master the art and science of interviewing by teaching them four levels of questions. By mastering each skill level, students can learn to explore change points more skillfully throughout their careers:


“What’s the difference between the man who left Augusta National a year ago and the one who’s about to return?” Tom Rinaldi, ESPN’s veteran reporter, posed this question to Tiger Woods as Woods was preparing for the 2010 Masters Tournament. Students can learn to ask questions in a “compare or contrast” format, giving the interviewee an opportunity to think about—and share—compelling ideas. This format also can help students discover hidden change points.


“Thinking back to when you first joined Siemens, what changes have you seen in your Infrastructure and Cities Sector customers?” Such a question encourages people to think more deeply about change points they’ve experienced in their organizations and at past and present points in their careers. Once students receive a response, they should learn to engage in two practices that are hallmarks of investigative reporters and market researchers: probing and clarifying. Students must learn not to take superficial descriptions at face value, but instead ask the person to share more that comes to mind on the topic. This approach can open the door to a trove of information that otherwise would have remained hidden.


“Thinking back prior to 2005 when you began to include a few enthusiastic Lego fans in product development, what’s the primary difference between products created only by Lego developers and those created collaboratively with your consumers?” This question builds on the previous two levels by adding in details that interviewers have discovered in their research. Once again, students should not be afraid to probe and clarify the person’s comments—in this case, once the person responds with one example, students could ask for yet another example, to give the person a chance to dig deeper. Sometimes it’s the next response that offers the revelation the questioner is looking for.


“You once said that even your own people thought you talked about megatrends such as population growth just because they were interesting, but in reality they were the ‘future of the company.’ How does the way DuPont currently determines its strategic priorities as a ‘science company’ compare with the way the company did so as a ‘chemicals company’?” As students do research, they might come across previous interesting comments someone has made. This will allow them to incorporate a verbatim comment into a comparative structure—which delivers the most powerful kind of question students can ask. People tend to take ownership of their comments, and they are flattered when an interviewer has taken the time to search for them in previous interviews and presentations. In addition, by including verbatim comments in their questions, students minimize the possibility of injecting their own views and maximize the person’s ability to delve into the topic.

By practicing mindfulness, students can tackle sensitive topics without turning an interview into an interrogation.


After students learn to explore change points in their questions, they must learn how—and in what order—to deliver their sequence of questions. For instance, they should understand that one of the secrets to capturing and holding someone’s attention with questions is to take that person into the moment of the topic. Questions that ask “what,” “how,” and “why” are designed to help people return more fully to important points in their lives and careers—for interviewers, asking such questions is a form of what many call “mindfulness.”

To master this particular questioning skill requires an understanding of both the Eastern and Western perspectives of mindfulness. For instance, the Eastern perspective holds that people remain in the present moment by focusing so closely on a topic that it becomes a meditative experience. The Western perspective, on the other hand, was pioneered by Harvard psychology professor Ellen Langer, who noted that “mindfulness is the process of actively noticing new things, relinquishing preconceived mindsets, and then acting on the new observations.” It helps us keep our minds open to possibility, she says, by “creating new categories, embracing new information, and being aware of multiple perspectives.”

In business, students can learn to ask mainly “what,” “how,” and “why” questions to encourage a person to stay in the moment. Such questions might take the following forms:

■ What happened when your company implemented Lean Sigma for private banking?
■ How was your coffeehouse company’s reward program affected when you started distributing products through grocery stores and pharmacies?
■ What was it like when the earth began to shake beneath your base camp at Mount Everest and you realized that an avalanche was headed your way?

When students are asking their questions face-to-face, they should practice watching the other person’s eyes. They’ll know they’ve crafted an effective question sequence when the person’s eye movements increase, indicating that they are returning to that moment.
When a questioner takes a subject into the moment, the questioner also must go into the moment. To do so, students should learn to maintain eye contact and minimize distractions. Peter Brook, English theater and film director, once complimented talk-show host and journalist Charlie Rose for this skill. Brook told Rose that he could tell that most of the people who interviewed him were thinking of how much time they had left and what question they were going to ask next. “But looking at you,” Brook said to Rose, “I can see a man in the moment.”

By practicing mindfulness, students also can better tackle sensitive, complex, or even politically charged topics. They will avoid turning an interview or meeting into an interrogation. Most important, they need to remember that a thoughtful interview will elicit mindful responses to their questions, while an interrogation will elicit only superficial reactions.



The best interviewers will begin a question sequence before the change point they’d like to explore—this approach is also a way to broach sensitive topics. Let’s say that someone was interviewing Zhang Xin, CEO of one of the largest property developers in China. He wouldn’t start by asking how it feels to be “the woman who built Beijing.” Instead, he might start by taking her back to her first work experiences with a question like, “What was it like to work in a Hong Kong garment factory, long before your net worth surpassed US$2.5 billion?”

In business, someone talking to Chanda Kochhar, managing director and CEO of India’s ICICI Bank, wouldn’t start by asking her how she transformed the country’s retail banking sector by introducing mobile banking in rural areas. Instead, she could ask Kochhar to describe an important experience that happened to her when she was a management trainee, and then build up to the point when Fortune named her one of the most powerful women in the Asia-Pacific region.

Empathy is part of an “input” mindset that is most conducive to asking good questions.

To teach this approach, professors could have students listen to ESPN sideline reporters like Holly Rowe, Maria Taylor, and Kaylee Hartung, who often begin their question sequence on an idea that occurred prior to the game-changing moment. As Sawatsky says, “If you start by asking how the person feels about winning the game, where do you go with your next question?”


When students stay in the moment with another person, they can be more empathetic. As it turns out, recent research by cognitive neuroscientists has opened new doors to our understanding of empathy. It shows that our brain’s anatomy and physiology help us go into the moment with others.

Empathy is part of an “input” mindset that is most conducive to asking good questions. People who have adopted input mindsets listen more than they speak, check their own emotions, and keep their personal views to themselves. This idea tracks with what Adam Grant at the Wharton School at the University of Pennsylvania found to be the distinguishing characteristics of top-performing salespeople. In his research, Grant has found that the best salespeople are not extroverts, but rather people who “are more inclined to listen to customers’ interests and less vulnerable to appearing too excited or overconfident.”

Research has found that the human brain has a mirror neuron system, which means that the actions and emotions of others are reflected inside our own motor systems. For instance, if we hear someone tear a piece of paper or kick a ball, the areas of our brains associated with such acts react almost as if we had completed the acts ourselves—researchers call this phenomenon “motor resonance.” In one famous study, the brain activity of subjects watching the scene in the film “Dr. No” in which a tarantula crawls up James Bond’s chest responded as if the spider was crawling up their own chests. In another study, brain scans showed that those viewing a film of someone wrinkling his face into an expression of disgust felt a similar emotion. Last September, research from the University of Vienna found that our brains experience “pain empathy”—when we see someone in pain, our brains simulate that pain as if we are feeling it ourselves.

However, empathy is not always an automatic response. When we observe members of an “out-group” who are not like us—if, say, we’re Liverpool soccer fans and we see someone wearing a Manchester United cap—our brains typically do not show motor resonance. But research suggests that our ability to empathize can shift dramatically based on our mindsets and motivation. That is, if we’re told to find someone wearing a Manchester United cap because he has important information for us, resonance becomes fully restored. One study showed that when subjects were told that empathy is a skill that can be improved, not a fixed personality trait, they made greater effort to empathize with those from racial groups other than their own.

To help students develop their empathy, faculty can give assignments based on recent research. For example, neuroeconomist Paul Zak and neurobiologist William Casebeer have found that watching a compelling narrative such as a movie or a theater production can cause our brains to produce two neurochemicals: cortisol, which triggers a sense of distress, and oxytocin, which triggers a sense of care. Students can learn to strengthen their own empathy by exposing themselves to narratives about people different from themselves—they can learn from classmates with different backgrounds or turn to books and film. By stepping outside their own experiences, they can improve their management skills.


By asking the right questions, managers can develop a level of judgment and insight that I believe most businesses are seeking. They can achieve what consultant David K. Hurst terms a second renaissance in management. Hurst calls for “a recovery of the concept of practical wisdom,” which he defines as “prudence, the context-dependent practical common sense needed when we have to make judgments about what is right and wrong.”

In fact, asking great questions is the sine qua non of ethical behavior. That means that instruction on the art and science of questioning needs to be part of a business school’s core offerings. Moreover, managers must not only be great at asking questions—they also must have the humility to listen to the answers. For this, business students must learn how to take themselves into the moment and decide what kind of managers they truly want to be.

David C. Steinberg is principal at Reykjavik Sky Consulting in Boston, Massachusetts. Steinberg conducts MBA and EMBA workshops and conference sessions on questioning skills, and this past spring he taught the course “Mastering the Art and Science of Asking Questions” to honors business students at Suffolk University’s Sawyer Business School in Boston.