Episode: 3 Questions All Great Leaders Ask

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Megan: Who? What? When? Where? Why? How?

Michael Hyatt: Questions. We begin asking them around age 2, and most of us never stop.

Megan: Hey, Dad, do I have to do my homework? Why can’t I go to Florida for spring break, and can I borrow the car keys?

Michael: The world is an amazing place. There are so many things to explore and wonder about. It seems everywhere you look there’s a question waiting to be asked and a discovery that’s just begging to be made.

Megan: Dad, how come you shiver when you have a fever, and if identical twins have the same DNA, why do they have different fingerprints?

Michael: These aren’t trivial questions. In fact, inquiries similar to these have led to some of the most important discoveries in science. It really is true that Sir Isaac Newton observed an apple fall from a tree and asked, “If the apple falls, does the moon also fall?”

Megan: Yeah, but did the apple really hit him on the head?

Michael: Well, no, but that question led to the formulation of the law of universal gravitation, which was followed by other breakthroughs in the field of mechanics, paving the way for the Industrial Revolution.

Megan: So are you saying a simple question can change the world?

Michael: It really can. Einstein wondered what would happen if you rode a beam of light. The question led to the theory of relativity. Walt Disney asked, “How can I create the happiest place on earth?” The answer, of course, was Disneyland. Steve Jobs asked himself this question every day: “If today were the last day of your life, would you want to be doing what you’re doing?” That question, perhaps more than anything else, drove the relentless innovation that gave us so many amazing devices.

Megan: Who? What? When? Where? Why? How?

Michael: Those are among the most powerful words in the English language, and they might be the six most powerful tools in a leader’s toolbox. By asking questions, we gain knowledge and insight. We uncover the truth about our situation and about ourselves. We find new ideas and better solutions. By asking the right questions we can move ourselves and others to unimagined discovery and achievement.

Megan Hyatt Miller: So if asking great questions is a fundamental task of leadership, what are the questions we should ask?

Michael: Now that’s a great question. I’m glad you asked.

Hi, I’m Michael Hyatt.

Megan: And I’m Megan Hyatt Miller.

Michael:  And this is Lead to Win, our weekly podcast to help you win at work, succeed at life, and lead with confidence. In this episode, we’re talking about the power of asking great questions.

Megan: As experts and leaders, we’re supposed to have all of the answers, so asking questions sometimes goes against the grain, especially when the questions become personal, but over a lifetime of leadership we’ve honed our question-asking skills to a fine art. Today we’ll show you the three types of questions all great leaders ask. By asking them yourself you’ll avoid becoming stagnated or committing foolish errors, and you’ll develop a sense of humility and curiosity that will supercharge your personal growth. Great leaders ask great questions.

Michael: Speaking of which, before we jump into these powerful questions, I have a question for you. If you love this podcast, would you please leave us a brief review? That’s a simple way of giving back, and it helps other leaders get ahold of the great content. It’s really easy to do. Just visit Thanks so much.

Megan: So let’s get into this topic of asking questions. I love this because I’m curious by nature, but I’ve noticed some leaders don’t seem to welcome questions. They don’t ask very many, and they don’t seem to like it when others ask them. Why do you think that is, Dad?

Michael: Well, first of all, I want to acknowledge you’re one of the best question askers I know.

Megan: Thanks.

Michael: I think it’s because you’re naturally curious.

Megan: I think it’s because I’m naturally introverted.

Michael: Maybe that’s the case, but your mom is not introverted, and she’s also good at questions.

Megan: That’s true.

Michael: Anyway, I think it takes a lot of humility to ask questions. There’s a sense in which leaders are expected (or maybe they expect this of themselves) to have all of the answers, so it feels uncomfortable to admit they might not know. Some come from a hierarchical context, such as the military, where obedience is emphasized, and sometimes we just fear what the answers might be. That’s why we’re afraid to ask.

Megan: I think great leaders ask great questions because they know they don’t know. There’s a fundamental sense that they don’t have all the information they need so they’re going to have to look outside of themselves for answers and that they just got where they are because they’re good learners. I think they’re students of other people, of human behavior. A good leader asks questions for those reasons.

Michael: They do. The smartest people I know and the most effective leaders I know are curious, because curiosity leads to asking questions, and asking questions leads to growth, and growth is essential if you’re going to be an effective leader.

Megan: Yeah, I agree. I really think it takes a sense of curiosity to ask great questions. You have to be fascinated by people. You have to look at the diversity of people and be really interested in their stories and their experiences and their take on the world. If you are, that kind of sets the stage for asking good questions, don’t you think?

Michael: I do, and I think it begins with a decision. We have to decide to be fascinated. We have to decide to be curious. It’s a posture of approaching life and approaching relationships. It also makes it much easier to be a good conversationalist when you ask questions, because people love to talk about themselves. They love to express their ideas, share their opinions, and if you can learn to ask the right questions, you’re going to be a hero and be seen as an effective leader. Contrary to what you may think, you don’t have to have all of the answers. If you have great questions, you’re going to be seen as a very effective leader.

Megan: Not only that, but you won’t be seen as stupid.

Michael: That’s right.

Megan: I say this because there have been so many times in my own leadership when (there have been plenty of times when I haven’t done this, by the way; I’ve learned it the hard way) I have asked questions when I felt maybe frustrated about something that happened in our team or frustrated by a result that was achieved or an outcome. What I have learned is that if I’ll ask questions, what I usually uncover is that it probably goes back to something that was my fault, that I didn’t clearly articulate my expectations or my vision was unclear or I said one thing and forgot about it.

That’s where that humility part comes in: realizing we’re fallible as leaders and very often it’s our own mistakes. This will keep you out of trouble if you’ll ask questions before you go after people or express frustration, because very often you’ll discover you’re at the center of your own frustration.

Michael: Well, and I think there’s another thing related to that. Sometimes, as leaders, we think we know what other people need to be doing or how to fix their problems or solve their issues, so it’s really easy for us to just tell, and it’s much more powerful (I’m still learning this, and I struggle with it) if people can discover it on their own, if they get their own insight. In other words, I can tell you what I think you need to do, but if I can help you discover that and come to your own conclusion it’s much easier for you to own it and actually follow through on it.

Megan: That’s right. I think that’s because curiosity strengthens leadership. Researcher Alison Wood Brooks reported one of the most common complaints people make after any conversation, including work meetings, is that they were not asked enough questions, which makes sense to me.

Michael: It totally makes sense.

Megan: They probably have expertise or things they would like to contribute, but instead, they’re just dictated to and they don’t have an opportunity to bring that experience or expertise to bear on the situation.

Michael: Have you ever sat in a meeting like that, where the leader made a decision and you thought, “I have information that would have been valuable in this, but I didn’t have an opportunity to share it”?

Megan: Sure. And I’ve probably conducted some of those meetings.

Michael: Yeah, me too. I hate that.

Megan: That’s why we have to be good students of ourselves and our mistakes. Great leaders ask three types of questions, and I’d love for you to talk about the first one.

Michael: First, questions that lead to understanding. Again, we’ve made the point, but it bears underscoring. That is, it takes humility to admit what we don’t know. The purpose here is not to judge or to lay blame but to assess the current reality. This is where we have to be careful about the tone with which we ask the question, because it can look like a question, it can have a question mark at the end, but it can sometimes be a rhetorical device for making an accusation.

Megan: That’s so true.

Michael: So we have to be careful that we’re not doing that, that it’s an honest question, that we’re asking it with integrity and authenticity because we want the answer even if it doesn’t align with our assumptions.

Megan: By the way, I heard once somebody say a great question to ask along these lines is “Now tell me where I’m wrong.” You make a statement maybe about what you think, but then you say, “Now tell me where I’m wrong.” Instead of, “I may be wrong, but…” you’ve actually given the invitation to the other person to tell you where you’re wrong, and, man, that opens up some really interesting conversation.

Michael: Yeah, it does. I remember when you shared that with me. I thought, “That’s a really good technique, and I’m going to use that.” We all know from our reading of The 7 Habits of Highly Effective People (Stephen Covey’s great work) that we have to seek first to understand, and this use of a question makes that possible. There’s a right and a wrong way to ask these questions. There are disempowering questions that are really statements, commands, or accusations, like when we say, “Why are you always late?” That’s actually not a question.

Megan: That’s an indictment.

Michael: Or “I think this is what we should do. Anybody disagree?”

Megan: That’s like the “Correct me if I’m wrong, but…”

Michael: Yeah, but it’s actually stronger than that. It doesn’t invite somebody to disagree with you. Those are disempowering questions, but empowering questions invite people to explore and share information, so they’re open-ended. Meaning, you really don’t know the answer before you ask it. I love asking those kinds of questions.

Like sometimes we use a question, we think we know the answer, and we’re hoping we can get that out of people, and if we can’t we’re going to keep asking until we get the answer we’re after, but the better question is to ask not really knowing what the answer is and then be surprised and fascinated by what you get. For example, you could ask, “What possible ways could we accomplish this?”

Megan: That’s a great one.

Michael: That’s where you’re inviting other people’s input and subtly and with humility admitting you’re not the only one who has this kind of information.

Megan: That reminds me of the monthly lunches you and I host with our various teams, our functional teams. One of the questions we ask during those lunches is, “What is one area of our business you feel like could be improved that we may be unaware of?” It’s so interesting to hear what comes out of those conversations, because very often it’s things we’re 100 percent unaware of. There’s no way we could know unless we opened up the floor for that kind of conversation, and we would be poorer for it if we didn’t create that opportunity.

Michael: Yeah, I totally agree.

Megan: One example that came out of that conversation was one of our executive assistants shared that she does a lot of work with outside vendors in her department and needs to coordinate a lot of cross-functional work and work with outside vendors. We’d been using a file-sharing solution that didn’t allow her to give access to vendors so they could make edits and collaborate on documents.

What that meant was every single time she needed to create a document and collaborate with an outside vendor she’d have to create a new document, send it, create all of those edits, then put the new one back in the file, or however it was. It was just super cumbersome. She said, “Man, if I could just fix that one thing it would change my whole job.” You and I looked at each other like, “Face palm. We can fix that this afternoon.”

Michael: And we changed everything.

Megan: Right. We ended up actually changing our whole system because of that, because she brought to light a problem many other people were having that we were just unaware of because we hadn’t asked yet. So, Dad, can you give us some examples of questions that seek understanding?

Michael: Let’s start with a simple one. “What happened?” Again, not with judgment, just assessment. Or “What do you mean by that?” Sometimes I think of this as the second question. It’s like you’re peeling the onion down to the next level.

Megan: Sometimes you will say, “Say more about that.”

Michael: Yeah, “Say more about that,” or “Could you elaborate that?” or “Could you say it in a different way?” or “How do you know?” Again, you have to be careful to not ask that as an accusation, but I like to know where people are getting their information or how they’re forming their opinion.

Megan: Sometimes I’ll ask, “Explain your assumptions of how you got to that conclusion.” Especially around financial information or other data it’s really helpful to understand, because very often you can understand what the root of the issue is if you know that.

Michael: What happens a lot of times there is that people aren’t showing their thinking. They’ve come to a conclusion and it has been a process, and sometimes we have to dig to get behind the conclusion to get to the process that led to that. Here’s another one that’s great. “Who knows more about this than we do?”

Megan: That’s one of my favorites.

Michael: And there’s always somebody. Or “What can we learn from this experience?” or (one of my favorites) “What does this make possible?” or “What have you been reading lately?” or “What are you excited about?” or “What resources do we have?” or “What didn’t go as planned?” Here’s a scary one, and I’ve written about this one. You have to be very careful about asking this one. “What was it about your leadership that led to that result?”

Megan: It takes a lot of maturity to ask that question because it’s a bold question, and it takes even more maturity to answer it.

Michael: It does, but what it does create is ownership and responsibility and moves you from being a victim to being an actor. That’s a whole other discussion.

Megan: Maybe we should do a podcast on that.

Michael: Maybe we should.

Megan: Terry Gross of the program Fresh Air has a great take on this. She says, “I’ve always been really curious about things and slightly confused by the world, and I think someone who feels that way is in a good position to be the one asking questions.”

Michael: I love the honesty of that statement.

Megan: I do too. If you can’t see or admit what you don’t know, you’re never going to grow. So what’s the second type of question?

Michael: Secondly, questions that lead to self-awareness. Tasha Eurich says self-awareness is the meta-skill of the twenty-first century. By the way, this is particularly important for leaders. These questions really do require a lot of courage, because they’re going to take you on an inner journey where you’re seeking a clearer picture of reality but of your own reality. In a sense, self-awareness is both inner and outer. Inner awareness is knowing yourself as you really are (and few of us do; it’s a journey). Outer awareness is knowing how you’re perceived by others, like the wake you’re leaving behind you. That’s why we need to ask these questions.

Megan: Yeah. You and I talk a lot about self-awareness. In fact, sometimes I feel like we keep going on this loop about it because it’s so important, and people may be wondering why we think it matters so much. What’s the big deal here?

Michael: Well, the big deal is that without self-awareness we alienate people without realizing it or we do damage without realizing it.

Megan: Or we’re just ineffective without realizing it or without understanding why.

Michael: Totally.

Megan: Dad, you and I talk a lot about self-awareness because we really believe it’s critically important, but what are some practical questions we can ask ourselves to develop that? If it’s the meta-skill of the twenty-first century, how can we develop it within ourselves?

Michael: Well, I think it’s important to uncover the machinations that are going on internally, because they’re driving our behavior. If we’re not aware of those, then those sort of subterranean, subconscious emotions are going to be producing results and we’re going to be a little bit bewildered as to what’s happening. So, for example, “What am I feeling right now?” This, by the way, is a question I ask every morning in my journaling, and it’s one of the questions we ask in the Full Focus Journal. “What am I afraid of? Why did I react as I did?”

Megan: That, by the way, is one of the most helpful questions for me, because I usually find out that what is the most triggering for me in other people is something that’s hitting me inside.

Michael: True to your own life.

Megan: Not necessarily that I replicate internally, but I can be very unconsciously triggered, and, man, can that get in the way of your leadership.

Michael: Yeah, totally. Here’s another one. “What do I really want in this situation?” Not just what I’m telling others, but what do I really want? What am I after here? “What am I grateful for right now?” By the way, another question in the Full Focus Journal, but a really important one. One of the things that’s great about this question is that it gets our thinking refocused in a positive direction.

The thing about gratitude is you can’t have anger coexist with it. You can’t be discouraged when you have that. So it’s helpful to ask yourself that question and be in a place of gratitude. “What is causing me stress or guilt or shame, and why is that?” Again, these questions are designed to be sort of an excavation tool to uncover what it is that’s driving our behavior.

Megan: The truth is that’s kind of the easier part, in some ways. The harder part is to ask the question of outer awareness. How do I become self-aware on the outside about my own wake? What are some questions there? Tell us a little bit about how to do that.

Michael: Well, first you have to make it clear to the other people with whom you’re seeking this information or this input that you really want the feedback. As a leader, because you’re in a position of power, people are going to be reluctant to do that, because we’ve all been trained in various situations that if we’re absolutely honest it might result in something negative for us.

Worst-case scenario, we could get fired. We could get demoted. We may not get promoted. We may get passed over. We may be perceived or branded as somebody who’s not cooperative, not a team player, or whatever. So we have to make it clear to the people we’re getting this feedback from that we really want it and that it’s important. Next you have to find a context where people can be honest with you. Probably not at an all-employee meeting.

Megan: You have to create a safe space or a safe container, sometimes people say.

Michael: Yeah, exactly. Then thirdly, you need to give them permission to be candid. I always say, “You can be honest. I can handle it.” The more unvarnished it is… I don’t mean cruel, but the more honest and raw it can be, the more helpful it’s going to be to me. Then ask for simple, specific feedback, like, “What’s one way I can help you by becoming a better leader? What’s it like to be in the room with me?” Ooh.

Megan: Yikes.

Michael: “What’s my greatest contribution to our team?”

Megan: We took our team out recently when you spoke at Leadercast. We were in Atlanta, and we took our leadership team with us. We went out to dinner as a team for two nights in a row, and we asked some questions. One of the questions we asked on the first night was, “How can I better set you up for success as a leader?”

In other words, “What do you need to be successful? What can I do, as your direct supervisor, to set you up for success?” I’m telling you what. I got some answers I didn’t already know. These are, in many cases, people who have worked for me and for you for several years who I know pretty well, but they gave some answers I was surprised by, and it was a really fruitful time of learning.

Michael: I know. I thought to myself as you were asking that question, as I was listening to some of the answers, “Why didn’t I know this before now?” Well, I’ll tell you why. Because we’d never asked the question before now.

Megan: Right.

Michael: Another question that’s a great question to ask is “What do you think I think about you?” Sometimes people have really out-of-alignment kinds of thoughts, like, “Well, I think you think I’m incompetent” or “I talk too much,” or whatever. I’ve asked that question several times when the answer was something that had never even crossed my mind. Again, people are creating their own stories, and this gives you a chance to align the inner reality and the outer reality.

Megan: Let me add two more questions that I got from our good friend Ian Cron, which, honestly, are kind of mic drop. First is “What do you know about me that I need to know but don’t?”

Michael: Yow.

Megan: Hello. I’m going on a date night with Joel tonight. I think that might come up. Secondly, “How wide is the gap between who I think I am and who others think I am?”

Michael: Wow. Those two questions, I promise… They’re scary to ask, but those would promote some serious self-awareness.

Megan: Man, they’re vulnerable but powerful.

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Megan: Great leaders use questions, first, to get understanding of their context and, secondly, to gain self-awareness. What’s the third type of questions great leaders ask?

Michael: Thirdly, questions that uncover possibilities. This is the one we typically think of, but it’s worth talking about how to do it better. Leaders are by nature problem solvers. Right? In other words, if there’s not a problem, you don’t need a leader. But the leader has to be able to envision the future. When faced with problems, people often default to disempowering questions, like, “Why does this always happen to me?” or “Why does this always happen to us?” or “Whose fault is this anyway?” or “Why did I let you convince me to try this?” This is shifting the blame to somebody else and becoming the victim.

Megan: This drives me crazy as a leader and even crazier when I find I’m doing it myself. These are really complaints with a question mark. It sort of reminds me of things the Israelites said to Moses in the wilderness.

Michael: That’s exactly why leaders need to ask questions that open up possibilities, not shut them down, like, “What does this make possible?” That’s a great question after a disappointment or failure. You have to be a little bit careful, because if you ask this right after, when people are experiencing the pain… You need to let them sit with it a little bit and acknowledge it, but if you can eventually get to the place where you can pivot and ask, “What does this make possible?” wow!

There are so many things… I’ve told this story many times about breaking my ankle. If I hadn’t broken my ankle, I wouldn’t have started blogging. If I didn’t start blogging, I wouldn’t have built a platform. If I hadn’t built a platform, we wouldn’t be sitting here today. That’s what breaking an ankle made possible.

Megan: That’s amazing.

Michael: Another question. “Who could partner with us?” or “What resources do we have that maybe we’re not aware of?” or “If we achieved this, why can’t we do that?” or “What action can we take right now to move toward our goal?”

Megan: Or “What would have to be true to get this result?”

Michael: Love that question.

Megan: That’s one of my favorites, because now you’re totally in the land of possibilities and you’re standing for the result. You really get people thinking outside of the box of limitations, which is what needs to happen to get a breakthrough.

Michael: It’s a great question to ask when people are stuck. I had somebody I was trying to convince needed to take a month-long sabbatical who was in a position where she could do that, and she just said, “There’s no way I could do that.” So I just turned it around and asked, “Well, what would have to be true in order for you to do that?” Then she started thinking. “Well, I guess I’d have to have enough savings in place. I’d have to have my business on autopilot,” and so forth.

Megan: Right. It’s amazing what your brain will come up with when you ask the right questions, and I think that’s the point here.

Michael: True.

Megan: The reason it’s so important to ask these questions that uncover possibilities is because leaders who can’t dream can’t lead. Fundamentally, the job of a leader is to create opportunities, to create vision, and to invite people into it, and very often questions are one of the best ways to do that.

Michael: Oftentimes, by enrolling other people with asking questions, it gives us a chance to collectively create a better, bigger future and to collaborate, and when you do that there is going to be more ownership in the future. When you ask these questions about possibility, it creates a better future for all of us.

Megan: Today we’ve learned that great leaders ask great questions. They ask questions that seek information, questions that seek self-awareness, and questions that open possibilities. I just want to remind you that asking questions does not weaken you as a leader; it sets you on the path for greater success. Dad, do you have any final thoughts for us?

Michael: Yeah, I do. First of all, I want to admit this is something I’m trying to grow in. I feel like I have a long way to go in my question-asking ability. I look at some other people, like your mom and, frankly, you, and I think, “There’s a lot more I could be doing in this area.” One of the things I’m trying to do right now is when I’m in a leadership context, maybe with a small group or with somebody else I’m trying to mentor, is that instead of making a statement I’m asking myself the question, “Is there a question I could ask instead that would open this up and create the possibility for greater insight for both of us?”

Megan: I love that. As we close, I want to thank our sponsor LeaderBox. It provides automated personal development in a box. Check it out at If you’ve enjoyed today’s episode, you can get the show notes and a full transcript online at

Michael: Thanks again for joining us on Lead to Win. If you like the show, please tell your friends and colleagues about it. That really helps us, guys. It helps us get the podcast up in the rankings and gives it more visibility and more listeners. We try to make this easy. All you have to do is go to There are simple instructions for leaving a review, and you can do it in two minutes.

Megan: This program is copyrighted by Michael Hyatt & Company. All rights reserved. Our producer is Nick Jaworski.

Michael: Our writers are Joel Miller and Lawrence Wilson.

Megan: Our recording engineer is Mike Burns.

Michael: Our production assistants are Aleshia Curry and Natalie Fockel.

Megan: Our intern is Winston.

Michael: We invite you to join us next week when we’ll be talking about the importance of taking a sabbatical. If you’ve never thought about that before or if you’ve thought it’s not attainable, it absolutely is, and I’ll show you how to do it. Until then, lead to win.