The Questions Leaders Need to Be Asking Themselves
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Welcome to HBR on Leadership.

Case studies and conversations with the world's top business and management experts, hand-selected to help you unlock the best in those around you. What makes a leader truly effective? Is it about strategic vision, time management, decision making, confidence? Robert Kaplan says the best leaders are exceptionally good at asking tough questions so they can make the right decisions.

Kaplan is the author of the book What to Ask the Person in the Mirror, critical questions for becoming a more effective leader and reaching your potential. In this episode, you'll learn how to frame better questions to help you get the answers you need to make decisions. You'll also learn how to use questions to clarify your four key priorities and then make sure you're spending your time in service of them.

This episode originally aired on HBR IdeaCast in August 2011. And just a note, we recorded this by phone, so while the audio quality is not great, the conversation is. I think you'll enjoy it. Here it is.

Welcome to the HBR IdeaCast from Harvard Business Review. I'm Sarah Green. Today, we're talking about leadership, which is a familiar topic, but we're talking about it in a slightly different way. I'm talking today with Robert Kaplan, Harvard Business School professor and author of the new book, What to Ask the Person in the Mirror, Critical Questions for Becoming a More Effective Leader and Reaching Your Potential. Rob, thanks so much for talking with us. Thank you for having me.

So I think what's interesting and different about this book is that it's framed around questions. And so many books in this genre seem to be focused on providing answers. Why did you take that different approach? Well, the reason I did this is...

I've managed businesses and I've worked with so many leaders over the years. And ultimately, when I go back and postmortem and think about what I should be doing in running businesses and nonprofits, and I sit with leaders in my office or in their office,

and talk through the issues they're facing, ultimately it gets down to questions. And I think through the most effective leaders that I've ever worked with, that I learned the most from and that were outstanding, and they were very good at asking questions. And what I've realized is the same types of questions

come up over and over again. And normally to the point that when someone is having a problem in a certain part of their business or nonprofit, their problem may not actually be what they think their problem is or the problem they're having is a symptom.

It's not the cause. And ultimately, when you're having a problem or you're frustrated or things are not going well, I found it is far more effective to step back and ask certain questions. Asana is where work connects. It's where projects, teams, and company goals are seamlessly intertwined with AI to propel your organization towards shared success. See why they're the number one AI work management platforms.

Try for free today at asana.com. That's A-S-A-N-A dot com. In the book, you also have a set of questions that would be useful for leaders at any level and very specific things about something like as seemingly small as managing time. That's something that

almost all of us struggle with. So can we get a little specific and talk about maybe how would you use questions to help manage your time? Okay. So in fact, let me go through a little bit of the setup. There are eight chapters, which basically eight areas of questions. There's the big, what seems like a macro question,

which is really a strategic question, what's our vision and what are our key priorities? And what the chapter goes through is lots of different ways to help people figure out how to ask and answer those questions and then how to put it into practice. And what happens is we go from the big, as you say, macro strategic down to the micro, including do you know your own strengths and weaknesses?

Do you know your own passion? Do you match how you spend your time with your key priorities? Do you even know how you spend your time? And for example, you ask about time. Most people may have a clear vision and priorities, but it doesn't occur to them that they actually should track. Let's say you work 60 hours a week, for example.

Break down those 60 hours. And I say to some people, measure it. See for a week how you're spending your time. Then compare that breakdown to your top four priorities that you've said are the most important things you and the business need to be doing. And almost invariably, there is often when a manager or leader is struggling, there's a mismatch, sometimes severe. And just think about it.

I'm a professor at Harvard. Well, okay, what are the three most important things I need to focus on to be a successful professor at Harvard? Okay, am I doing them? Well, not quite, and not always. And why does that happen? Especially when you're a leader. I've got people at my door. There's a crisis that comes up. I have some old habits that, gee, CEO always did X, Y, and Z, so that's what I'm always going to do. Even though it doesn't fit the priorities anymore. I'm

I'm out of date. Maybe I've just gotten into some bad habits. So what I'm trying to do is jar people. Sometimes asking a question will jar you. And if I say to someone or say to you, does your time or myself, does my time match the priorities? And I actually make myself go through it. I go, oh, boy.

And when I meet with a CEO and they just take me through it, I don't need to say a word. They say, oops. And then I'll say, well, why are you spending 15 hours a week on X, Y, or Z? You know, the truth is, Ryan, I never thought about it. I don't know. It's what I've always done. We were a small business once. And I always did this when we were small. I never stopped doing it when we got bigger. And so what it allows people to do is say, you know what? I need to adapt. I need to change. It's like the light bulb goes on.

And then they learn, okay, I need to strive to do this. And by the way, you may go for several months where you got a good match and then all of a sudden the world changes again. And maybe, you know, you need to be out more with customers and you haven't made the adjustment.

You just haven't done it. I need to spend more time out with customers. And boy, if I measure my time, I realize I'm spending almost no time. I knew I wasn't spending enough time, but I didn't realize it was so little. And then you realize you've got a problem with all your people where they're watching you. You're telling them to go out with customers, except you're not doing it. And so there's one chapter here on what signals do you send? Are you a role model? Because leaders are ultimately do lots of things. One of them is your role model. People will imitate you.

And so if you're not asking these questions and trying to drive these issues, my guess is people are going to mimic you. And then you get out of alignment. So there's a chapter also in this book on clean sheet of paper. What do you mean by that when you say clean sheet of paper? And this sounds so innocuous. By the way, all the questions in this book, you talk about low tech. These are brutally important.

simple questions, very plain, simple, no highfalutin questions here. They're very basic. So one of them is, do you look at your business with a clean sheet of paper and decide whether what you're doing still works? And one way to ask this question is if let's say we're starting over from scratch,

Is this really the way I would organize this company? Are these the people I would hire? Are these the tasks we would do? Are these the markets we would serve? And this sounds like a very simple question, and most leaders, including me, often don't do that. And why? It's emotionally extraordinarily difficult to do. I'm running a business. I'm comfortable with the way I'm running it. I'm comfortable with our setup. I've gotten in a routine. And

This requires me to take a step back and face some tough realities. And because it is so emotionally difficult to do, the best advice I give to many CEOs, and I used to follow this myself, take a group of three or four of your up-and-coming people. There's a chapter on succession planning. Take some of your up-and-coming people, future leaders. Give them this assignment.

Take yourself out of it. Give them this assignment. Ask them to do this analysis. If they had to start the business from scratch, how would they design it? And they're not so emotionally tied to it the same way we might be. And then tell them in advance, I may not take all your advice, but I want to hear your recommendations. And they will come back invariably when I've seen this done. Fabulous, fabulous insights.

And it sometimes, it makes it easier for the leader to realize, you know what, there's more buy-in than I thought for this. People at the point of attack, near the close to the customer see this, and we actually need to try to do some of these things. That's what I mean by the looking at the business with a clean sheet of paper. We invariably do this. Listen, people who are successful individually and who run organizations have to ultimately

Look at reality, compare it to what they're doing. And if you're a business leader, you've got to do it. And if you don't do this, ultimately the market will do it for you. It'll put you out of business or your board will do it for you.

Well, of course, that means that the leader has to be more on his or her toes as well. It does. But, you know, a lot of people think, and we've had some government leaders, very famous leaders who sort of say, leadership is about saying, we're going to go north, northeast and follow me. And here's what we're going to do. And that's what my people expect of me. And they don't want to see vulnerability. They want to see confidence. And they want to see me make decisions.

They come to me for the answers. And I actually don't think that that is necessarily – there's some of that that a strong leader needs to do. But I think an extremely strong leader, ultimately a very strong leader, is willing to stop and say, I don't have all the answers, actually. I'm concerned about the following. I want to frame a question. Let's discuss it. And so one nice thing that does for the leader is you actually don't have to know everything, which you're not going to anyhow.

And you don't have to pretend you do. And it takes a great burden off people to know that. And number two, rather than spend your time thinking of the answer, maybe a better use of your time is to think about, gee, are there two or three questions I should be asking? And how should we orchestrate a discussion

so that we can actually figure out together what the best thing is to do. And we're going to come up with a better answer and a solution, a plan of action than if I tried to do this myself. And I think that actually, it reorients the focus of the leader, takes a burden off that leader, but also requires a different type of preparation, as you say, be on your toes, a different way of being on your toes. So I guess the central point there is that if you're not asking good questions, you're never going to get good answers.

No. Listen, part of being a leader is there's deciding what you believe and acting on it. But part of a leader also is, to your point, is learning to frame, get better at framing issues and asking questions and orchestrating debate and listening. All the things I just talked about require listening. And that's one of the most powerful tools and assets you have as a leader is listening.

Asking a question and then listening shows a lot of respect to someone. If I ask them a question and I listen carefully what they say, it's a very powerful tool the leader has and it's underused. Well, I think it's some great food for thought. Rob, thanks so much for talking with us today. All right. Thank you. That was Robert Kaplan in conversation with Sarah Green on HBR IdeaCast.

Kaplan is a senior fellow and professor emeritus at Harvard Business School. He's also the author of the book, What to Ask the Person in the Mirror, Critical Questions for Becoming a More Effective Leader and Reaching Your Potential.

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 at hbr.org.

This episode was produced by Anne Sani and me, Hannah Bates. Ian Fox is our editor. Music by Coma Media. Special thanks to Maureen Hoke, Nicole Smith, Erica Truxler, Ramsey Khabbaz, Anne Bartholomew, and you, our listener. See you next week.