Episode: 4 Questions That Will Transform Your Leadership

Michael Hyatt: I have a story about the first time I discovered that questions can shift everything and change everything about the course of your life. Gail and I had been married about five years. We had two little girls, Megan and her sister Mindy. I could sense that we were drifting apart in our marriage. I was very busy at work, trying to make a living, trying to get a promotion to make more money, because we always seemed to be about 10 percent short every month. I thought, “If I could just get that next promotion, we’ll have enough money to cover everything.” It was kind of a moving target. All that to say I was spending a ton of time at work.

Gail and I began to drift apart, and I said, “You know, this is a problem that is not good.” I saw it, and I’m ashamed to admit this. People laugh out loud when they hear this. I saw this as Gail’s problem. I had no self-awareness that I was part of the problem. I just said, “She doesn’t seem to be romantically interested in me like she used to.  I thought, “She has an issue with this, and I’m going to do the thing I should do, and that’s send her to counseling.” I know; it’s sad.

So she dutifully went. She didn’t even question it, which was amazing, but it was a long time ago, a less enlightened era. She went to counseling. After about four weeks, she came back and said, “Well, The counselor has requested that you come to my next session.” I was indignant. I was like, “What do I have to do with this? First of all, I don’t have time for this. I don’t have time for counseling. Second of all, this is your issue to resolve. I’m trying to be supportive. I’m paying for these sessions, but what do you mean I need to come to this session?”

Long story short, she finally convinced me I needed to come. So I went, with a lot of fear and trepidation, because I’d never been in therapy, I’d never talked with a counselor, and he had a doctorate. I thought, “Whoa!” It was intimidating. We made some small talk in that session, and then he said to me, “Why is it that you think you’re so driven?”

It was the first time I’d ever thought of myself as being a driven person or that maybe my work was out of balance, but I knew intuitively and instantly that he was right, and I burst into tears. I thought, “I’ve been caught. I’ve been outed. She’s not the problem; I’m the problem.” That began a very, very significant and important change in my own life, in my own self-awareness, and in my relationship with Gail. Yeah, I guess that was the first time I saw that the right question answered at the right time can change everything.

I’m Michael Hyatt.

Megan Hyatt Miller: And I’m Megan Hyatt Miller.

Michael:  And this is Lead to Win, our weekly podcast designed to help you win at work and succeed at life.

Larry Wilson: And I’m Larry Wilson. Today we’re talking about four questions that will transform your leadership. Leaders are called upon to give answers all the time, and the problem is that sometimes there’s just too much data. It’s easy to make simplistic solutions. Really, we’re in a time when leaders need to begin asking deeper questions, and that’s what we’re here to talk about today. Michael, that is a powerful story and very revealing and vulnerable. It just makes the point: finding the right question can change everything, and that’s really what we’re talking about today.

Michael: It’s really important for leadership too. I used to think, as a young leader, it was all about having the right answers, and what I’ve realized, particularly as I’ve gotten older, is it’s really about having the right questions. When I’m coaching clients, we can move the ball down the field to a certain extent by me giving the answers, but if I ask the right questions and people do the work themselves and come to the conclusions themselves, that’s a whole different level of transformation.

Megan: By the way, asking questions is way more vulnerable than having the answers. Not only because you’re admitting you don’t know something but because you kind of don’t know what’s going to come out from the other person. You don’t know what your question is going to elicit. You don’t know what kind of catalyst that’s going to be. It requires courage to ask it, and then it requires discipline to shut up and let people answer. It’s really hard.

Michael: And these can’t be rhetorical questions where you already have the answer and you’re trying to lead people to the right answer that you have in your head. You have to suspend what you know and assume the posture of a beginner and say, “I don’t really know. This is an honest question I’m asking you.”

Larry: We’re talking about four powerful questions that will transform your leadership. The first question is a question every 2-1/2-year-old learns, and I know this because my granddaughter has just learned it. That question is…Why? When a leader asks the question “Why?” what does that question do?

Megan: First of all, it clarifies the problem. So often we think we understand something or know what’s going on, but unless we ask, we probably don’t have the full picture. Asking “Why?” helps us to clarify the problem. It also helps us to analyze the cause and effect. For example, if I’m trying to understand a financial result we got and I start asking, “Why?” my understanding of what led to the result is much greater, and, therefore, my ability to come up with a good solution or to get a good solution from our team is so much better than if I had just taken things on their face or blown past some things I didn’t fully understand without that question of “Why?”

Michael: We often think of using this question when we’re thinking of a negative result, like, “Why did that go off the rails? Why didn’t that project work? Why did we experience this failure?” but I think it’s equally important to ask the question about positive results, like, “What made that so successful? Why was that successful?” I think of our Full Focus Planner, for example, which has been a wildly successful product that we just introduced about 18 months ago, and to ask the question of the team, “Why did that work?”

I think at the time we had some ideas, but to unpack that gives you the opportunity to replicate it. For us, as we began to unpack that, realizing people still had an affinity for something that was a physical artifact, for something that was physical that they could touch and interact with, also led us to the conclusion that maybe people would interact better or learn content better in a live events scenario where they could actually be with other people and experience a real-life interaction as opposed to an online course. So asking the question, “Why?” led to the ability to replicate it.

Megan: Another great thing about this question, another twist on it, is asking somebody, “Why is that important?” or “Why is that important to you?” will reveal so much. I find every time I ask that version of the why question I get an answer I didn’t expect. There’s something about either people’s motivations or understanding of themselves or a situation that is very different than what I saw on the surface that I never would have seen without asking, “Why?”

Michael: To go with that several layers deep… I don’t know if you remember back a couple of weeks ago when we were doing Best Year Ever Live, but there was a particular speech I had to give on Wednesday night of the conference that I had never given before. It was an optional session we did on how to scale your business with success, so it was primarily directed to business owners.

I was a little bit nervous, because I’d never given the speech before and there was a lot of content. Gail asked me in the greenroom before I went onstage, “Why is this speech important?” So I gave her a reason. Then she said, “Well, why is that important?” She went five levels deep to where I got to the point where I was so moved I said, “Because I think this is why I was created.”

Megan: That’s about as deep as you can go.

Michael: It was about as deep as you can go. I said, “If I don’t do this, I’m not fulfilling my destiny.” Well, then all of a sudden I had this amazing confidence to go onstage and deliver this speech, because I connected with my why. But it wasn’t just because she asked the question one time. She kept peeling back the onion, peeling back the whys until we got to the middle of it, sort of the foundational level of it. It was really profound.

Megan: I love that.

Larry: That, by the way, is what my granddaughter will do when you give her an answer why. “Why? Why? Why?”

Megan: Kids are so good at this.

Michael: I have one other thought about this. As leaders, one of the things that should mark our leadership is curiosity. We ought to be curious about things not only that we don’t understand but about things we think we understand. Sometimes if we ask people questions about things we think we know, we’re going to get a whole different nuance or whole different distinction we didn’t have before. So I think to stay curious is important.

Larry: You bring up an important point. I want to reference a study from Harvard Business Review of 16,000 employees, so, a fairly widespread sample. Of C-level executives, so, chief level…CEO, CFO, COO…84 percent say curiosity is encouraged a great deal or a good amount in their workplace. Only 52 percent of the individual employees said the same thing.

Michael: That’s a gap.

Larry: Yeah, there’s a gap there. Leaders may think they’re fostering curiosity or that they themselves are displaying curiosity, and maybe they aren’t. What do you think accounts for that gap?

Michael: Well, I think those why questions are typically asked more in the C suite and more among executives, and as you move down an organization it’s probably less likely to be asked. I’m not saying it should be less asked, but I think it’s less likely. It’s more of control and command at the bottom level of the organization. “I need this task done. Go do it.” Or maybe people feel more intimidated, like they can’t ask it.

This is one of the reasons why, in various contexts, I’ve created situations where I have met with my frontline teammates so I can get unfiltered information from them and ask why and, more importantly, give them a chance to ask why. So often, they’re doing things that don’t make any sense, and if they knew the reason why it would reinvigorate them or give them an opportunity to challenge it and say, “Well, that’s a dumb reason, because we don’t even do that anymore.” Unless we give that opportunity to do it, there’s not that opportunity for us, as leaders, to learn and grow.

Larry: So, how do you put yourself in the frame of mind to ask that question? Leaders, I think, want to be in control and want to be seen as in control. They don’t want it to appear that nobody is running the ship. You ask too many questions it maybe makes you look ignorant. How do you get in a headspace where you can ask these open-ended questions?

Megan: Well, this comes up for me with the leaders who are on my team often. It’s something I’ve coached them on and something I coach myself on. One of the biggest reasons we don’t ask these questions and we’re just not in the right headspace to do it is because we’re moving too fast. We’re in that turbocharged, efficiency-driven mindset. We come into a meeting and it’s all about making decisions or getting a desired outcome. Get in, get out, and go to the next one.

What I have encouraged my leaders to do and what I have to remember myself is to slow down. Remember you’re meeting with humans who have a whole unique perspective, unique challenges, see things differently than you do, and you need that. When you ask a question, you have to stop. Then you have to step back and kind of distance yourself emotionally enough or try to get to a neutral place where you can hear their answers, because sometimes you’re not going to like what you hear.

Then just to create that space, literally to pause long enough for people to answer, because if you’re not careful, what can happen is you jump in with the answer to your own question because you think you know the answer, and then that shuts everybody else down.

Michael: Exactly right. That’s where, as a leader, once you ask that question, if you are going to give an answer you have to give it last. Some people would think you need to go first, and sometimes you do, particularly if you’re asking other people to be vulnerable. That’s when you do need to go first, because you’re going to set the pace in terms of self-revelation, so you have to go first. But if it’s not that kind of question, if you’re asking them, “Why didn’t this work?” or whatever… If you give your answer, that’s going to be seen as the definitive answer, and it’s going to shut off communication, so you want to wait until the end.

Larry: Michael, I liked your example of asking, “Why was this product successful?” but there must be other why questions that have been important in your life or in your business. What are some of the great why questions leaders should ask?

Michael: “Why does this situation exist?” Usually, something we find not useful in our current organization was put there at some point because that was the best solution to another problem, but then we lose sight of that problem, and now there’s no reason for that thing to persist. So we have to ask ourselves the question, “Why does this situation exist? Is it still relevant?”

Another question: “Why does it present a problem or create an opportunity?” Maybe somebody objects and says, “Well, this is a real problem.” Just challenge that and say, “Why is that a problem?” and drill a little bit deeper. Maybe it’s an opportunity. Or “Why has the problem not been solved before now?” You have to be careful with this. One of the problems with some why questions is that they invite a lot of unproductive speculation.

Megan: Or it’s really just a statement in disguise, like, “You’re an idiot.”

Michael: You don’t want to do that. People can tell the difference. “Why did you allow that to happen?” If you say that, that’s an accusation disguised as a question. It has to be an honest question. Another one is, “Why should we spend energy on this?” or “Why should we spend capital on this?”

Megan: I love that one, because it forces everybody to think and really create a rationale for investment, and that causes some great breakthroughs.

Michael: It does. It’s easy to come up with good ideas, start marshaling the resources, and quickly get overcommitted.

Larry: Has this been a hard lesson for you guys to learn, that you need to ask questions?

Michael: I would say it has been hard for me, because I’ve had a lot of success in my career, which has resulted in arrogance. I have oftentimes thought to myself (I would never say it out loud because I want to appear humble), “I know the right answer” or “I have the best answer. So maybe I’ll entertain other answers, but then once I roll it out it’s going to be the best answer,” until I realized that most of the time my answer wasn’t the best answer and other people had really great ideas and great answers and that if I would wait I would get better answers and I wouldn’t limit the growth of my company to my perspective but I would enroll and enlist the help of everybody else.

Larry: The first question for leaders to ask is “Why?” The second question (and I love this question) is…What if? Megan, what does this question do when you ask it?

Megan: I love this question too. In our company, people ask this all the time. Sometimes we have to throttle it back a little bit, because we ask it so much we can come up with a thousand new ideas. It really identifies possibility and questions the process. It’s kind of like nothing is sacred. If you ask it right, nothing is sacred and everything can always be improved, which is really exciting and, for some people, probably terrifying.

I love to ask this, because it opens up the future. It also allows your imagination to go to work, because now, instead of thinking about what is, you’re thinking about what could be. The obstacles aren’t yet there. Certainly, they are going to pop up when you start asking this question, but if you can learn to push them to the side and just say, “We’ll get to you later,” then what you come up with will often be much bigger than you ever thought possible.

Michael: Where I first learned this was when I first encountered a spreadsheet program. This was way back in 1981.

Megan: This is so geeky.

Michael: I know. Back in 1981, I bought a PC. Very expensive, by the way, particularly as a percentage of my total income. Very expensive, and I had to buy it because my company didn’t see the value in it, but I bought it for one reason. I bought it to get a copy of VisiCalc. Remember that? Larry will remember it because he’s old enough.

Megan: No, I was 1 year old at that time.

Larry: I’m not that old, Michael.

Michael: Well, VisiCalc was sort of the precursor to Excel, and we were allowed to create “What if?” business scenarios. You could model a business, model different variables and extrapolate what the results would be or what the impact would be in your business if you did that. Now, all of a sudden, it opened up all of these possibilities, because you could dream about possibilities, you could model it on paper, so to speak, before you ever had to commit the resources to it.

That’s the thing I like about “What if?” thinking. It opens up the possibilities about the future. It allows you to think expansively about different scenarios, and you can do that before you actually have to commit. That’s where some of the best thinking in an organization is going to happen. “What if money was no object? What if we had the time and resources? What if we had additional staff people? What would we do? What would we do if we were going to start over from scratch? How would it look?”

Larry: Do you find that people resist the “What if?” questions?

Megan: I think it depends on their personality type. I know we’re going to talk about personality in another episode coming up, which will be fun. Certain people are naturally given to change. They just embrace change. They love it. Certain people are a little bit more risk-averse and it’s more challenging, but I do think regardless of where you fall, even if maybe it’s not natural for you, you can learn to see the value of this and begin to incorporate it more in your life, even if your brain doesn’t go there all by itself. What will happen if you do it consistently enough is you’ll see the results. You’ll see how things can grow and develop and where opportunities come from when you open your mind to this question.

Larry: Let’s imagine you’re talking to someone…not that there’s anyone in this room, certainly probably not listening to this podcast…who likes things to stay the way they are and who doesn’t take so quickly to change. How do you put yourself in a frame of mind where you can question these possibilities and open it up to the “What if?” question? How do you get there?

Michael: One of the things you have to understand is the distinction between a growth mindset and a static mindset. As an organization, you have to prioritize growth. I’m not talking just about revenue growth or profit growth but growth in everything. Are you, as an organization, committed to getting better at what you do…getting better at serving your clients, getting better at business processes, getting better at the hiring process? If you are, then asking this question is the fastest way to get better.

“What if we did it this way rather than that way? What if we did this with a machine rather than a human? What if I delegated this rather than try to do it myself?” We happen to have growth as one of our eight core values. If you prioritize growth, if you teach on that to people, if that becomes the underlying assumption that’s the bedrock below this question, then I think people are more responsive, because they go, “Oh! Oh yeah, this is that growth thing. We want to grow. We want to improve. We’re committed to wow,” or whatever.

Larry: So it’s, in some ways, a function of culture.

Michael: Definitely.

Larry: I heard you mention, Megan, a great “What if?” question: “What if money were no object?” What are some other “What if?” questions that could open our minds a bit?

Megan: One that has been really powerful for me is, “What if I were brave?” I have a long history of being terrified of public speaking. And not just big public speaking, like hundreds and hundreds of people…any public speaking, at all, up in front of people. That has gotten progressively better over the years, but I took it on in a big way this year and did two keynotes in front of collectively probably about 1,500 people between two events. That was so far out of my comfort zone. I mean, this podcast was so far out of my comfort zone when we started it more than a year ago.

At some point (and it was not when we started the podcast; it was really leading up to the first keynote I gave), I was asking myself, “What would it be like if I wasn’t terrified? What would my life look like?” I started to realize how many things I was missing out on, how many opportunities there would be for me to make a difference in the lives of other people, not just in our own audience but in other areas I care about. I realized the stakes were too high, that I couldn’t afford to stay scared any longer. That was a very personally powerful question for me.

Michael: I just had a mental image as you were talking about this. What happened this last year for you is I think you took a big swan dive from a very high diving board into the deep end of the pool not even knowing if you could swim.

Megan: Absolutely.

Michael: And as it turned out, you’re a very good swimmer.

Megan: But I wouldn’t have known that if I hadn’t asked, “What would I do if I were brave, and what would it be like if I wasn’t scared?” I’d never considered that possibility my whole life. It was like this was just an attribute about myself that was absolute.

Larry: The first question that will transform your leadership is “Why?” The second question is “What if?” That brings us to the third question…How? How does this question function for you? What does it do in your organization when you ask, “How?”

Michael: It immediately drives to execution, to implementation, to “How are we going to take this lofty idea and actually make it happen?” I like the how question, and you could get stuck on this question because you might not know how. You might need to bring in an outside resource to help you get to where you need to go, but it is a question you have to ask. I think it’s easy in some organizations with some kinds of culture…

In fact, I was just on a call the other day for a board I serve on, and they wanted to talk about the why, they wanted to talk about the what, they wanted to do all the brainstorming, but when I asked the question, “How? How are we going to make this happen?” everybody froze up, because that meant work. All of a sudden, somebody was going to have to take responsibility. Somebody was going to have to do something. As a leader, we have to constantly have a bias toward action and constantly take all this brainstorming, all of these good ideas, and reduce them to the level of implementation. Otherwise, we’re just wasting time and resources. Do you agree with that, Megan?

Megan: I totally agree with that. I don’t think I’ve ever heard you talk about it in exactly that way, but that’s certainly what we practice at our own company, and the results have been pretty great. Asking “How?” is also the antidote to feeling overwhelmed. Certainly, you can feel overwhelmed when you ask, “How?” if you make it too big, but the real question is, “How do we chunk this down into actionable pieces?” It’s like when we talk about goal setting. What are the next actions that should be inside your comfort zone? When you start to do that, now you have a path forward to making it happen, and that’s why this question is so important.

Larry: Now some people will use this question (I’m sure you’ve observed this) as a defense. You come up with a “blue sky” idea. “Well, how are we going to do that?” It’s intended to shut down creative thinking. How do you frame this question or when, maybe, do you frame this question so that it’s constructive and not obstructive?

Megan: Well, you can’t ask it too early. When we’re in meetings and we’re ideating or thinking about the future, we will shut this question down, because asked at the wrong time it’s very counterproductive. You have to ask the question of “Why?” and “What if?” and fully let your wings spread in those two questions before you get really practical, because if people aren’t connected enough to the vision, then the how can feel overwhelming. If they are connected to the vision for something and are super excited about it, then their brain starts going into problem-solving mode, and “How?” becomes not a shutdown question but an empowering action-based question.

Michael: I think of it almost as three levels of questions. You have to ask, “What?” or maybe “What if?” to kind of open it up. “What if we did this? What if we did that?” Then you have to narrow that down to “What is it that we actually want to do?” and you have to get clarity about the what. Then “Why?” is really the question about purpose. “Why does this matter?”

Those questions have to be asked. You have to have clarity on what you want to do. You have to be clear about why you want to do it. Then the “How?” question makes sense. In other words, if this is something I’m really clear I want and I have some substantive reasons of why I want it, then asking “How?” becomes the doorway to actually getting it done and not shutting the door or preventing us from thinking further about it.

Larry: So, the first question that transforms leadership is “Why?” The second question is “What if?” The third question is “How?” The fourth question is…What would have to be true? What does this question do for you?

Megan: I think this question brings together the other three, because it takes the possibility of the why and the what if, that possibility-making part of those questions, and the practicality of the how, and it helps you to think bigger about how you could accomplish something. So, what would have to be true? Instead of focusing on why it can’t happen or what’s in the way, you start to think with possibility about if you were going to go ahead and do this thing, what would have to be true for it to be possible, for you to move forward with the how?

That gets exciting, because then you start to think, “Well, this would have to happen, and this would have to happen, and this other thing would have to happen.” Then you’re going to ask “How?” again, probably. “Well, how we would make those things happen? Well, this would have to be true, and that would have to be true.” It really keeps you from getting stuck with the limitations that exist in your mind.

Michael: It’s a great question to ask when somebody throws up an objection to why you can’t do something. For example, I was coaching a client a few years ago, and I was telling them about my recent sabbatical, that I’d taken 30 days off. I said, “Have you ever thought about that?” She said, “There’s no way I could ever do that.” She said, “I’m just in a business where I have to see patients, and I can’t imagine being away from my business and me being able to make an income.” So I said to her, “Well, before you go there, what would have to be true in order for you to take a 30-day sabbatical?” It completely shifted her thinking.

Megan: Now you’re in solution-land. Like we often talk about, this is really shifting from scarcity, “There are not enough resources to do the how of what I want to do,” to abundance, which is all about there are endless resources, and it’s just about identifying what you need and then going after it, which is all about what would have to be true.

Michael: Megan, you and I did this this morning. I’m not going to reveal the product we were talking about because it would give it away and we need to do some more thinking about it, but there was a product that we said would never be in a specific format, and I started asking myself the question yesterday, “What would have to be true in order for that product to be in that format?” My mind began to explode, and I realized, “You know what? It’s possible.”

Megan: The truth is that happens every single time you ask this question, “What would have to be true?” Whether it’s delegation or leadership or expanding your staff or growing your profit. It doesn’t matter what it is, when you ask this question, the future starts to be unlocked. It’s so exciting.

Michael: There’s another one where we’re asking it right now. We’ve talked about getting additional location space for some of the live events we want to do, and that’s something that in the past, as the CEO, I would have quickly dismissed as, “We don’t want to invest the resources or tie up the capital.” So then I started asking myself the question, “Well, first of all, what would it make possible if we had that space?” which is another great question we’re not talking about today. The second question is, “What would have to be true in order for us to do that?”

Larry: Today we’ve learned that in this time of easy answers, leaders need to ask deeper questions. Four of the most transformative questions are “Why?” “What if?” “How?” and “What would have to be true?” Any final thoughts today, guys?

Megan: If you’re finding yourself stuck as a leader or you’re not getting the results you want, instead of going to search for answers, start asking great questions. I think you’ll be encouraged and surprised and excited with what you discover.

Michael: I just want to recommend to people a book I’ve found enormously helpful on this topic: The Coaching Habit.

Megan: Oh, that’s such a good one.

Michael: It’s by Michael Bungay Stanier. I’ve interviewed him on video before. He’s a great guy. This is a great book, and he has a list of questions that are enormously helpful.

Larry: Megan, thank you. Michael, thank you.

Michael: Thank you, Larry, and thank you guys for joining us on Lead to Win. Join us next time when we’ll show you three tools that’ll help you understand how your team thinks so you can set them up to achieve. Until then, lead to win.