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Kurt Nickish
Why is asking questions sort of this basic conversational skill so hard for people?
Arnaud Chevalier
Well, I think we've all heard it, right? Asking more questions help people make better decisions. But there's a dark side, right? Because whenever you're asking one question, you're not asking another type of question. And so if you're under time pressure, you might be probing one side of a problem or decision, but not other sides. And if you look at managers compared to other professions, lawyers, physicians, psychologists, they're trained to ask better questions. Managers seems like we are supposed to learn on the job, and many do.
Kurt Nickish
Learn it and perhaps learn a certain kind of question that seems to work for them for some time. You point out a lot of people don't understand that there are different types of questions that you can be asking and they just by their nature tend to ask a certain type of question but avoid other ones just because it doesn't come naturally to them.
Arnaud Chevalier
Yeah, that's what we find speaking with managers and leaders across organizations. Right. I think professionally you develop your own mix of questions. Maybe you pick up a couple questions that you think are insightful from your boss, perhaps you get to learn and hone that mix and it gets you here. But it's unclear when you get promoted to your next job that what got you here will get you there. We are trained, we are told, ask open ended questions. Ask follow up questions.
Kurt Nickish
Yeah, ask why. Ask the five whys.
Arnaud Chevalier
The five whys, absolutely. But what else? You get to the point, sure, good idea. I should ask why, what else should I ask? And usually the guidance falls flat. Right. So we've been speaking with hundreds of executives trying to understand which questions they ask. We've been speaking with very senior people trying to understand what works for them. And out of that we came together with a taxonomy of questions that we believe are useful in making better decisions in solving complex problems.
Kurt Nickish
This taxonomy basically divides strategic questions into five investigative, speculative, productive, interpretive, and subjective. It's probably smart for us to go through them kind of one by one.
Arnaud Chevalier
Let's. Because that's a mouthful. Right. So let's project ourselves into a big decision that you have to make. Maybe as a manager or maybe as just a person, perhaps you're thinking about buying a new house, maybe moving the family, maybe you're thinking about acquiring a new firm. Whenever we're faced with those complex decisions, pretty quickly we want to identify, okay, what is it that we want to achieve, but we realize we don't have enough information to achieve it. We need to get into investigative mode by asking ourselves what's known, what's known about the problem, for instance, the five whys, or what's known about the solutions, the potential solutions, by asking how? How may we do this? How may we do that? So the first type of question is investigative. Helps you probe in depth into the problem or into the solution.
Kurt Nickish
Some of the questions that can be asked here are what happened? What is and isn't working? What are the causes of the problem? Those are all examples of investigative questions. Are these questions that are typically asked at the beginning of a process or can they be used sort of anywhere in problem solving?
Arnaud Chevalier
Yes. What we're finding out is it works better actually if we go back and forth. There's no real segmentation because investigative gets you to a point, you drill deeper into the problem or into the solutions. But going deep is not the only way. Right. You may want to speculate as well. The second type of question is speculative questions, epitomized by what if? So speculative questions are here to help you foster innovation by challenging the implicit and the explicit assumptions for the problem.
Kurt Nickish
What if is really good. Examples of this are also like, what other scenarios might exist? Could we do this differently? That's a way of just asking a simple question, but trying to open up a brand new avenue of thinking or problem solving.
Arnaud Chevalier
Exactly. And by doing this, you're really expanding the space in which you operate. Right. So investigative you go deep and speculative you go wide. And you're stretching a little bit the universe of possibilities.
Kurt Nickish
Now, productive is the next type. Tell us about that.
Arnaud Chevalier
Yeah, so investigative you go deep, speculative you go wide. If you're a professor, that's all you have to do. You can spend years and years on your problem, but if you actually have a real job, chances are you asked to have some results. Right. So productive is the now what kind of questions. You're adjusting the pace of the effort, deciding whether you know enough to move forward right away, or perhaps deciding that you need to slow down a little bit before you make that decision to give you a chance to get even more insight into your problem.
Kurt Nickish
Examples here that you list in your article are things like, do we have the resources to move ahead? Do we know enough to proceed? Are we ready to decide? So very kind of tactical. And the sorts of questions that sort of bring everybody back to sort of the realization of what needs to happen.
Arnaud Chevalier
That's right. How are we doing across compared to project plan and should we accelerate or should we slow down?
Kurt Nickish
I can definitely see certain types of managers would be really good at this right there, you know, there are roles sometimes that are very operational or, you know, process oriented. And you, you almost have a traffic police officer managing a process. Yeah. So interpretive was the, the next type.
Arnaud Chevalier
Investigative, what's known? Speculative. What if? Productive. Now what? All this gets me some information about my decision about my problem. But information is one thing, but it's, it's not quite wisdom. The fourth type, the interpretative questions, the so what helps us convert that information into insights?
Kurt Nickish
Examples here are questions like, how does this fit with that goal? What are we trying to achieve? That really gets it? So what, what did we learn from this new information? This seems very helpful at a transition point where you've, I don't know, you've Gotten customer data back or you have new information to process.
Arnaud Chevalier
I love how you phrased it because this is also what we're discovering. The so what helps you transition from one type of question to another? So the five whys. Why aren't we having better revenues? Because our current clients are not buying enough of our products. Okay, so what? Maybe then that will help me transition from being investigative as can why to perhaps being speculative thinking about how else we could get our clients to buy our products. So it enables you to transition from one type to another.
Kurt Nickish
Now, the last type of strategic question that you identify in your taxonomy is subjective, which was really interesting to me because it just. It wasn't one of the sorts of questions I expected to jump out it in a strategy framework. Tell us a little bit more about subjective questions.
Arnaud Chevalier
Maybe it's helpful to explain how we got to those. The first four types. We were very happy when we got there. We figured it was really clicking. And then we had the catchy way of thinking about it. It's four types, but there are really three main ones like the three musketeers, that sort of things. We thought we were done and then we started interviewing top leaders, people in charge of billion dollar operations. And there was something else. And maybe this is best exemplified by this wonderful little cartoon by Jack Ziegler in the New Yorker a few years ago where you see a little fish happily swimming around, minding its own business, not realizing that right behind it there's a huge fish about to eat it alive. And the small one is called agenda and the big one is called hidden agenda. The last type of questions, subjective questions, are just realizing that we're dealing with people. People have emotions, they have political agendas. And if we don't embrace this, we might just miss entirely what the problem is actually all about.
Kurt Nickish
Examples of these questions are how do you really feel about this decision? Have we consulted the right people? Those are all things that do get at those emotions and just the real impact of business decisions.
Arnaud Chevalier
Right, Right on. I remember specifically we were interviewing the CEO of a major airplane manufacturer and brilliant fellow, mid-40s everything, former engineer, I think. So we were expecting him to be very investigative. Nothing against engineers, right? I'm one myself. But turns out that he was saying after every big meeting he would sit down and reflect on was there a difference between what was said, what was heard, and what was meant to him? What really mattered was that human component in the meeting.
Kurt Nickish
Now that we have these five types, let's go through some of the advice that you have in your article. Number one is you really want people to understand what kind of questions they tend to ask or what their own sort of interrogatory typology is. Talk more about that.
Arnaud Chevalier
I think it's fair to say that we all develop our question mix. The questions that have served us well that we believe will serve us well in the future. I remember, for example, interviewing the COO of a major car company and he's telling us how on Monday morning he meets his team and he's asking them, how was your weekend? But he also made it very clear that when he's asking, how was your weekend? He doesn't want to hear about little Timmy's baseball game. He wants to know whether we shipped on time, if there's any issues with the manufacturers, any. In other words, he is in full productive mode and that makes a lot of sense. Again, he's a coo, right? His job is to get things moving. But we can also imagine that he's doing such a good job at the COO level that he might be offered the CEO position. And here, if he's using the same mix that is predominantly into productive, he might not see other areas. He might develop some blind spots.
Kurt Nickish
And so, number one, you can learn to mix it up yourself by understanding your type, basically keeping track of the questions that you ask and making a concerted effort to ask different kinds of questions so that you expand your repertoire. That's one way to get started.
Arnaud Chevalier
Maybe another way is also to take the LQM test, the leader's question mix test that we are putting together on the IMD website. It takes five minutes and you're given two batches of questions and you tell us which one you prefer. And as a result, we help you identify what your preferred mix is. And back to your point, Kurt. My preferred mix is one thing, but I shouldn't be. I need to realize as well that there are other questions, including some that I'm not familiar or comfortable with, and that what matters is not so much my preference as much as what is needed for the specific decision or specific problem I'm facing.
Kurt Nickish
So if you've assessed your current question style, you start to adjust your repertoire. It's still a lot to keep track of. Like when you're in conversations, it's easy to remember afterwards, why didn't I ask that question while you're in it? Especially if it's a heated exchange or very pithy conversation, it's hard to just do this in real time on the fly, really well. So what kind of advice do you have for somebody to practically keep track and expand their repertoire, but also make sure that they're not missing anything and that they still don't have blind spots even after they try to expand the zone in that way.
Arnaud Chevalier
I think you're describing situations that we see often with the executives. And one way of doing this is by taking the lqm, the leader question mix assessment. You also get a list of questions and you can take that list with you, especially if there are some types of questions you realize you don't ask very naturally. You can also pick a couple of those ahead of a meeting, making a mentor or written note to ask those questions over there and see what happens.
Kurt Nickish
Does this work at all levels of the organization or are we really talking about leaders asking strategic questions?
Arnaud Chevalier
We've applied it at all levels. Absolutely. And in fact, what we found is in teams it works even better realizing first that we have different mixes and then identifying, so what being interpretative, what are we going to do with the fact that you and I have different mixes? Maybe if I'm terrible at one type, for instance, speculative, maybe I need to rely on my teammates who are better there. Or at the very least, learn to recognize the value of speculative questions, at least in some settings. Not shutting down the door the moment I hear a speculative question.
Kurt Nickish
And one point you make in the article too, is that you can find people on your team to help compensate for you if you know that you have certain weaknesses. Let's talk a little bit about the difficulty of asking questions, though, in business settings, because when you ask a question, in some ways you're putting people on the spot. What advice do you have for managers and leaders? And asking questions in these settings where you can ask penetrating and provocative questions but not make them feel so, you know, hard edged.
Arnaud Chevalier
Yeah, I think again, you're putting your finger on it, right? Because if you're the authority figure and you ask why did you do this? Chances are the person on the receiving end of that is going to feel threatened. So there is what we ask and there is how we ask it and how we phrase it, and what we found with those leaders who are particularly good with these subjective kinds of questions is they are very conscious of the way they ask things. So, for instance, you might not ask why did you do this, but perhaps what happened?
Kurt Nickish
Can you give us some examples of where these questions, or changing your mix, asking different types of questions, being more deliberate in your question, asking how that can lead to better business results?
Arnaud Chevalier
Well, my favorite, of course, is A Swiss cliche, you know, if you ask IMD professors will tell you, of course we'll bring it back to the Swiss army knife. And your mix really is a Swiss army knife. You should be able not to have just one blade. But you have different mixes of questions and you use the mix that best fit whichever situations you're in. Take the example of an airline captain who's about to land at Geneva airport. If I'm in the back of the plane, I do not want the captain to start thinking speculative questions. Hey, what if I turn this knob here? Or what if I try to land the plane in a different way? No, no, no, no. Her job at that time is to land the plane, be productive. You take the time you need to decide, no more, no less, and you just get it done right. But that same captain, maybe a few minutes before, might have to deal with an issue. Maybe a passenger who had drunk too much alcohol and started to act up and maybe she needed to on the spot, think creatively and perhaps using seat belts to restrain the passenger, and perhaps even earlier in the day when she first met the first officer who was going to assist her on the flight, she needed to create quickly an environment where they could work well together. She maybe needed to be very subjective in her question mix so we can see how the same person on the same job might have to fundamentally alter her mix just to be effective at all three decision points.
Kurt Nickish
You also have a lot of good examples in the article of companies that or leaders that didn't ask a certain type of question and that led to a huge problem.
Arnaud Chevalier
Being French, we can make fun of.
Kurt Nickish
The sncf, who this is the French rail company.
Arnaud Chevalier
Yeah, that's right. They ordered 15 billions worth of trains and design spec'd them on the assumption that all platforms were some standard size. Only to realize that all the platforms, all 1300 of them, were actually larger needed to be respect. And I think in hindsight it's always easy to make fun and to look at deficiencies in the decision process. However, we probably can safely assume that engineers on the problem did their utmost to get it done. So really five question types as a way perhaps of having a checklist of reducing the chances of having blind spots and realizing then that if we are not mindful about the questions we ask, we might just every now and then fail to check an important question category.
Kurt Nickish
One question that you suggest asking is, are we all okay with this? Which is a powerful question. It also presupposes that you've got the psychological safety on the team for everybody to be able to speak up. So questioning and asking the right questions at the right time still demands an awareness of the culture that you're asking it and how these questions are going to come across and whether you've created the climate for people to be able to give you the kind of powerful answers that you're asking for.
Arnaud Chevalier
Now, this is a very good point. And we've worked with organizations where there was very little psychological safety, where admitting that anything might be less than perfect might be a big, big issue. And in those settings it's much more challenging. But there are ways of still eliciting the wisdom of the group. One such way, for instance, is to use pre mortems and to project the organization say, okay, let's go with this decision. Let's assume that we are picking option one and we are now three years from today and we realize it's a total fiasco. It crashed down, what happened. And that can help people who would probably not ask questions frontally to put on the table some less than perfect aspects of the decision they're seeing.
Kurt Nickish
Yeah, that's very clever. What could go wrong? What did go wrong with this fiasco? And is there anything different about today's business climate with artificial intelligence that amplifies the ability to ask questions?
Arnaud Chevalier
So I think you're spot on, right? Genai, especially since late 2022, enables you to be aspiring partner or to have aspiring partner in having back and forth. So you can indeed have a conversation with the database now, and you can't have that conversation by proposing answers. You need to be asking questions. So clearly asking more insightful questions might unlock some value you couldn't otherwise.
Kurt Nickish
So for a speculative question, what does that look like in a real business setting?
Arnaud Chevalier
You hear meet managers who are often risk averse, and then you speak with their boss and the boss is always asking for taking more risk. And you can rationalize it from both sides, right? Because the boss has a portfolio of a project and if some of those fail, no big deal. But if I'm the manager in charge of a project and I have it fail, then pretty quickly I start thinking that people associate me with failure. And so asking what if having that conversation between the top team and the manager saying, what if we didn't care about failure? What if we were looking for each of us managers, some of us having some failure, what if we relaxed this constraint? Or that constraint can help us realize and realign what would be individual objectives with organizational ones.
Kurt Nickish
Do you remember any good stories from the executives that you talked to where asking some of these subjective what's unsaid kind of questions really opened up new opportunities or changed things. Yeah.
Arnaud Chevalier
And this one really gets to the human dimension. If you ask me next Monday morning how I am doing and I reply fine. Fine can be a number of things, right? Fine can be my dog died yesterday, or fine can be life is beautiful. What we found with some of the execs who were really good at going to the essence of it is probing in a caring way to understand the meaning behind the words, what's kept unsaid, and remembering that you have short posed people and you have long paused people. Some people will say fine as just an introductory, but if you give them a little bit more time, they might actually expand and through that unlock a set of information you wouldn't have had access to.
Kurt Nickish
So, Arnaud, I have to ask, you've done all this research. I'm curious if you have a favorite question that you never asked before, that you've come out of this process with, that you use in your work and your job.
Arnaud Chevalier
Right. Putting me on the spot, huh?
Kurt Nickish
A little bit.
Arnaud Chevalier
I really fell in love with that difference between what was said, what was heard, and what was meant. I really think this is something I need to be better at and reading the weak signals and understanding what's behind the words. But whenever I take the test, and I've taken it several times, what comes out is I'm terrible at productive questions. So maybe, just maybe, I need to pay more attention to the pace of my decision making.
Kurt Nickish
For a manager who's not a leader yet hasn't developed their repertoire per se, what can they do tomorrow to start asking more strategic and stronger questions?
Arnaud Chevalier
My advice to someone who feels they don't have yet a mix is, first of all, you probably already have a mix. There's probably a couple of questions that you've seen or heard and they feel very insightful. But maybe you want to do as I do is I keep track all the questions I hear on your podcast and elsewhere that I haven't heard before. I keep a long list and then I categorize them under the five buckets and I have my favorite ones.
Kurt Nickish
Arnaud, thanks so much for coming on the show and sharing this research with us.
Arnaud Chevalier
My pleasure. Thanks for having me.
Host
That was IMD Professor Arnaud Chevalier in conversation with Kurt Nickish on HBR Ideacast. Chevalier is a co author of the HBR article the Art of Asking Smarter Questions. We'll be back next Wednesday with another handpicked conversation about leadership from Harvard Business Review. If you found this episode helpful, share it with your friends and colleagues and follow our show on Apple Podcasts, Spotify, or wherever you get your podcasts. While you're there, be sure to leave us a review. And when you're ready for more podcasts, articles, case studies, books and videos with the world's top business and management experts, you'll find it all@hbr.org this episode was produced by Mary Dew and me, Hannah Bates. Kurt Nickish is our editor. Music by Coma Media and special thanks to Ian Fox, Maureen Hoch, Erica Truxler, Ramsey Gabaz, Nicole Smith, Anne Bartholomew, and you, our listener. See you next week.
Podcast Summary: HBR On Leadership
Episode: The Best Leaders Ask the Right Questions
Release Date: May 14, 2025
Introduction
In the latest episode of HBR On Leadership, Harvard Business Review delves into the critical skill of asking the right questions—a fundamental yet often underdeveloped aspect of effective leadership. Hosted by Kurt Nickish, the episode features Arnaud Chevalier, a professor at IMD Business School and co-author of the HBR article "The Art of Asking Smarter Questions." Together, they explore how strategic questioning can enhance decision-making, foster innovation, and improve organizational dynamics.
The Importance of Strategic Questioning in Leadership
Kurt Nickish opens the discussion by highlighting the paradox that while asking questions is a basic conversational skill, many leaders struggle to do so effectively. He poses a thought-provoking question: “Why is asking questions sort of this basic conversational skill so hard for people?” [02:19]
Arnaud Chevalier responds by acknowledging the complexity of questioning. He notes that while asking more questions generally leads to better decisions, the selection of questions is crucial. Leaders must navigate the balance between different types of questions to avoid focusing too narrowly on one aspect of a problem, potentially neglecting other important factors. “Whenever you're asking one question, you're not asking another type of question,” Arnaud explains [02:27].
Arnaud Chevalier's Taxonomy of Questions
Chevalier introduces a comprehensive framework categorizing strategic questions into five distinct types: Investigative, Speculative, Productive, Interpretive, and Subjective. This taxonomy is designed to help leaders diversify their questioning approach to cover all facets of complex decision-making.
Investigative Questions
Focus on digging deeper into problems or solutions. Examples include:
Speculative Questions
Encourage creative thinking and innovation by challenging existing assumptions. Examples include:
Productive Questions
Address the practical aspects of decision-making by focusing on actionable steps. Examples include:
Interpretive Questions
Translate information into meaningful insights. Examples include:
Subjective Questions
Address the human and emotional dimensions of leadership. Examples include:
Developing a Balanced Question Mix
Chevalier emphasizes the importance of leaders understanding their own questioning styles and actively working to diversify their question mix. He suggests that leaders naturally develop a preferred set of questions through their experiences and mentors but must remain adaptable to avoid blind spots. “What matters is not so much my preference as much as what is needed for the specific decision or specific problem I'm facing,” Chevalier advises [14:14].
He introduces the Leader's Question Mix (LQM) test—a tool developed to help leaders identify their predominant question types and recognize areas needing balance. By assessing their question mix, leaders can consciously incorporate a variety of question types to enhance their decision-making processes [14:14].
Implementing Strategic Questioning in Organizations
The discussion moves to practical applications of the taxonomy within teams and organizations. Chevalier highlights that effective questioning is not solely the domain of top executives but is beneficial at all levels. In team settings, recognizing each member's question mix can lead to more comprehensive problem-solving by leveraging diverse perspectives. “If I'm terrible at one type, for instance, speculative, maybe I need to rely on my teammates who are better there,” Chevalier explains [16:21].
Overcoming Challenges in Asking the Right Questions
One significant challenge leaders face is asking penetrating questions without making team members feel threatened or defensive. Chevalier underscores the importance of how questions are asked, not just what is being asked. He provides examples of reframing questions to be less confrontational, such as asking “What happened?” instead of “Why did you do this?” to create a safer conversational environment [17:36].
Additionally, Chevalier discusses strategies for environments with low psychological safety. Techniques like pre-mortems, where teams anticipate potential failures and discuss what might go wrong, can help surface concerns in a non-threatening manner [22:04].
Practical Advice and Tools for Leaders
Chevalier offers actionable steps for leaders to enhance their questioning abilities:
He also shares anecdotes demonstrating the impact of strategic questioning, such as a COO who tailors his questions to focus on productivity during operational meetings but may miss broader strategic insights needed for higher-level roles [13:53].
The Role of AI in Enhancing Strategic Questioning
The conversation touches on the evolving role of artificial intelligence in leadership. Chevalier notes that generative AI (GenAI) tools can serve as effective partners in conversation, enabling leaders to engage in more insightful and iterative questioning. This technological advancement can help unlock value by facilitating deeper inquiry and more informed decision-making [23:14].
Conclusion and Key Takeaways
Arnaud Chevelier concludes by reflecting on the personal growth that comes from adopting a balanced question mix. He shares his realization of the need to improve his ability to interpret unspoken signals and manage his productive questioning style. This introspection underscores the importance of continuous development in leadership skills [26:16].
Key Takeaways:
By mastering the art of asking smarter questions, leaders can significantly improve their effectiveness, drive better business outcomes, and cultivate a more dynamic and responsive organizational environment.
Notable Quotes:
This episode underscores that effective leadership is not merely about having the right answers but about asking the right questions. By embracing a structured approach to questioning, leaders can navigate complex challenges with greater clarity and purpose.