471 How to Ask Better Questions and Lead Through Uncertainty with Larry Robertson

Welcome to Partnering Leadership, a top global leadership podcast for purpose-driven leaders with a growth mindset, seeking to learn from the leadership journey of change makers and business insights from leading global thinkers. For additional leadership insights and bonus content, visit us at partneringleadership.com. Now here's your host, Mahan Tavakouli.

Larry Robertson, welcome back to Partnering Leadership. I am thrilled to have you with me.

It is an honor to be here again. Thank you for having me.

You joined the podcast, Larry, believe it or not, was more than four years ago, episode 125. Wow. Aired January 2022 on your book, Rebel Leadership. Can't wait to talk about your newest book, Great Question, The Art of the Ask and Getting More of What You Really Want. What a powerful way of framing that. So what I wonder, Larry, you have studied leadership, you have written about leadership. Why this focus on questions now?

I'm going to split that into the two pieces. So why the focus on questions and then the now part? The primary reason for the focus on the questions was in my work, in my advisory work, but also in my research around the books. And my books have been on the topics of entrepreneurship, creativity, leadership, but specifically leadership and uncertainty, and then, of course, the new book. And in the first three, in each of those topic spaces, questions played a very prominent role. They make for more effective entrepreneurs over a lifetime, not in any one moment, but over a lifetime. They allow creatives to actually create value, tangible value, something more than their ideas or a figment of their imagination. And with leaders, especially leaders in uncertainty, if they're not asking questions constantly, not only can they not be sure of the path they're on, but they get late signals, if they get any signals at all, when they should be changing the path for an opportunity as much as for a threat. So I knew that those elements were there, that questioning was powerful in each of them. And every project, Mahan, every book project, I would end the book, meaning finishing the work and say, I really should look into that question thing more. And when you read the books, you'll see there's a lot about questions. But this idea of coming back and saying, is there something greater? So that pattern has always been there as a push. But the now part, I think, is what's really important. If you look back over the past 25 years, roughly this century, this new century, there has been a global shift away from questions. And it started out as a very steadily growing thing, and now it's becoming a little bit more exponential. What do I mean by that? I mean that more often than not, we're making statements, that more often than not, when we ask a question, we're setting up to confirm a statement or to make a statement. Sometimes we're using questions to taunt. Sometimes we're using questions to see if we have allegiance with the people that we're asking it from and wanting nothing else from it. And so this movement away from questions is a curious thing, but I also think it's a very dangerous thing. Because when you look at the research on leadership and business in general, when the uncertainty goes up, the question should as well. Because if the uncertainty goes up, at the very least, it has the risk of undermining the assumptions on which you've based your business model, your management style, your company culture, everything that goes with it. At a minimum, you've got to ask questions as to whether or not you're still on track with those things, whether or not you remember your assumptions and if they're still relevant, and what's new that you should be incorporating. So when I see us moving away from all, that was a signal to me that really pushed me over the top to say, I have to look deeper into this.

That's a powerful point, Larry. And a couple of things I wonder about it is I see societally as the level of uncertainty in our world has picked up. It seems to me people are looking more for certainty from their leaders. Do you see that as well? Because what I hear from you is the level of uncertainty is going up. So we need more curiosity and therefore we need to ask questions. But I almost see the opposite. People are looking for certainty in their leaders because they feel so much uncertainty in the world.

Oh, I'm going to amplify what you just said. Because it's not just the people who are looking to their leaders and wanting, expecting, hoping for some kind of certainty. And we can think about all the obvious reasons why. You certainly feel a lot better about your situation, about yourself, and so on, if you can say certain things are certain. But there's a reinforcing mechanism with how all of us think about leaders. We look to leaders to have the answer. We look to leaders to fix things. We look to leaders in some organizations to pass all that certain information down so we can just continue to be followers. And leaders are taught to expect that of themselves, that if they're doing the job right, then somehow they're going to fulfill that mythology of having the answer to everything, of even being able to, one individual, to get their mind around the scope of business today. You take the smallest business, you take the simplest business, whatever minimizing adjective you want to put with it. And even those businesses are so complex right now. The way they have to incorporate technology, the number of places that they have to look for competitors who compete against them, how they bring resources to them, all of those things make for a very complex picture that cannot fit in any one person's head. So this mythology, even though it keeps going, is a really dangerous thing in these times as leaders have to take on more. And to get any of it done, they need to share that leadership with everybody on their team and everybody in their organization. It's a collective solution these days to virtually everything.

Couldn't agree with you more on that. Now, the other side of this that I wonder about, Larry, before we started recording, we were talking a little about AI and AI's implications. AJ Agribal talks brilliantly about prediction machines and how the cost of prediction will drop as accuracy of prediction goes up. So I wonder, will that therefore increase certainty and reduce our need for questioning or increase it in that we are going to have much more certainty in predicting a lot of things in our lives and in our organizations? How do you see that interplaying with the kind of questioning that you are talking about?

First of all, we have to think about how most AI is built. It's looking at data that's already happened, right? It is predicting, but it's predicting based on data that I'm going to just work in broad brushstrokes, is basically in the past. So in order for those predictions to be accurate, then a large portion of what the past was that generated that data has to be true in the future. So do we really believe that in the level of uncertainty that we're all living and working in these days, things are going to stay that much the same? I would put a question mark on that at the very least. But the second thing is that let's pretend that was going to stay largely the same, or we're talking about an application of AI where we can say, okay, but the data's pretty much the same. What are we trying to do with it? Are we working towards efficiencies, again, that would have worked in the past or work in this moment? Or are we looking for something that allows us to adapt better or to innovate or to create out of things that aren't even there right now? If you look at most of human progress, it's what I just described in the last 10 seconds. And so in order to do that, it requires a kind of thinking, a kind of exchange, a kind of acceptance and willingness to make mistakes that is not built into how most AI is programmed at this time. So I would argue that while it can be helpful in many ways, if we're looking towards the future and we're living in both an uncertain now and an uncertain future, AI is a great supporter and it helps with a lot of efficiencies and crunching data. But at the same time, we need things that are bigger than that, and I would say more human than that if we want to keep progressing.

What a powerful way to frame the importance of that human involvement and human judgment in the creativity that it takes to build the future rather than just rely on the predictions of the past. Beautifully said, Larry. Now you open your book by calling it a yield guide rather than a traditional field guide.

So oftentimes a field guide, just for comparison and looking at the more typical, oftentimes a field guide says, the author is saying, This is how I did it. If you follow, you'll get the same. That's not really what we want from any kind of guide. We want something that yields whatever we're after, hopefully yields something greater than what we're after, and continues to yield going forward. That's really what I mean by a yield guide in the larger sense is that you want to be able to understand, understand questions and use questions in a way that not only help you to get more of what you want, but really help you get more of what you really want. The really word is very important. And I say that because we all want yield, but we tend to formulate yield as something that comes out of a set of actions and we get it in this moment. What we really want is yield ongoing. What we really want is to create value that's lasting. What we really want is impact that has some staying power to it. So that's the primary reason that I call it a yield guide. But there's one other secret reason in there. And that is that even though this book is built to help any one person to, as I say it, master the art of the ask, to really get good at question asking and asking greater questions. At the end of the day, to get that yield, questioning is something that you have to do collectively. And in order to do that well, it means that individual leader we talked about a few minutes ago, the one that has all the answers and can fix everything, has to yield to others who share in figuring out the solution, creating the innovation, whatever it might be. So there's a yield of a different type as well, which is to say nobody knows it all, but we can know a lot more together. That's where the yield guy comes from.

That becomes essential in a world that's becoming more and more complex. Therefore, the questioning is important, but part of what you're saying is the highest yield is a questioning culture, not necessarily a questioning leader.

That's absolutely right. That is absolutely right. And in addition to a questioning culture, so this is interesting. Whenever we think about questions, ultimately what we're hoping for is the invitation to ask. We don't always get that invitation to ask, but we want that invitation. So when somebody says, okay, we're going to develop a more questioning culture in our organization, each of us individually, even if we're not conscious of it, is thinking, I get to ask more. But what a questioning culture really means is everybody gets to ask more, which means that there's a portion of the time when you are asking. There's another portion of the time when you're at the very least listening. But I would suggest have to go a step further, which is to have the intellectual humility to realize, and this is the definition of intellectual humility: one, that there are things you don't know. Two, that the things you know might be wrong for the particular situation or problem they're working on. And three, that might ask you to change in order for things to become better. So if you think about a questioning culture, it's really about helping everyone to realize, including the leader, that there's this balance that everyone is asking, not just a handful of people, that the answer comes from many, not just one. And that when you are not asking and answering, you're learning. So this is the interesting thing, Muhan. There were five patterns that I saw across my research that ultimately lead to great questioning. And very quickly, there are five C's core, which is really this sense that we need questions. They are core to everything we do. We are a questioning species as much or more than we are anything else. But then listen to the next one: context. Context is really understanding where your questions are taking place and why they matter. And we don't often connect the two. We think we do, but we don't often connect the two. We already talked about the third one, and that's concession, which is not just asking, but this listening and weighing how much you know versus how much you do know, sometimes changing. Then there's this fourth pattern of the five, and that's connection. What are we trying to connect our questions to or towards? And then finally is continuation. It's this idea that question asking is not linear. Question asking is loopy at best. You could say it's circular, but it's really loopy. And so the reason I lay those out is that if those are your mentality, it doesn't mean that you're always asking a question, that you're always forming some sentence with a question mark at the end. You're looking at the dynamics that go into great questioning all the time. What's the context? What are we trying to connect this to? How does this relate to how we treat one another in an organization and what the culture is? So you're doing a lot more of watching that while you both invite and allow the questions to be asked. And you're realizing that the only reason you're together trying to figure out how to work with one another in this way is you're trying to get somewhere which takes answers.

You also say in the book that we thrive on questions. The human brain thrives on questions. Why is that?

That is a very good question as to why it is. What I can tell you is that the research on this is across disciplines. So the belief is shared from anthropology to early childhood development to the study of creativity and more, that we are not just a questioning species, but we are born asking. So this is a, I think this is a really interesting, very simple, but really interesting distinction. Before we acquire language, which is how most of us think about questions, we're asking, how do I get fed? Where do I find a place that I can get rest? Who can I count on to give me those things? Is this space safe enough for me to play in, to figure things out? Before I ever utter a word, and we're questioning each in our own way, taking feedback in and continuing to question. This is what makes us a questioning species at our core. And when you look at the research, it says that up until about the age of five, that's how children operate. They have certain things that restrict them, whether it's their family life or it's communal things or it's teams that they're on. It's not until they get to their formal education, and particularly in public schools, that we start to put some rules around question asking. But from a birth, from an evolutionary standpoint, that's our survival tool. It's the thing that drives our curiosity. It's the thing that leads us to create, not just to be curious, but to make something. So it's there underneath all the other things that we would credit. And it doesn't go away, it just gets covered up. So it's really there as a fundamental feature of every one of us. It's just that many of us are out of practice in using it. Why wouldn't you use that most powerful tool that you rely on from the minute you come out into the world?

Is it that we've been out of practice as a result of modern education, modern society, or has that happened over time as well, Larry? I'm just curious because there are a lot of different authors, many of them I respect, talk about the power of questioning. And everyone talks about how kids, they're always questioning, and then they get the wrong answer, and the teacher says this is the right answer, they stop questioning. So is it that education has taught us that or other things? Because you say our brain thrives on questions. What has taken it away from us in order for us to then dust it off and go back to the way we should be?

So there are three things I want to touch on that you said. One is there is no one resource, place, or person to blame. So I would never say, oh, it's all about education. Education just beats this out of us. No, that's not true. And if you think about the typical public school, all the people who work in a school are meeting the requirements and the guidelines of other people, from a superintendent to parents who vote a certain way, a school board, whatever it is, even national standards. So they're trying to meet those things. When they teach, they're given a restriction on how they do that. You only have so many hours in a day, and your students must advance this far in this grade during this year to get to the next one. So even just in that one example, it's hard to point a finger at anybody. Even the people who are imposing the rules and the guidelines on a school, I think we can assume they're generally well intended. So we're trying to do multiple things as human beings. We're trying to advance and accomplish. When we go through one heck of a fight to do those things, we'd like to maintain the easier path we found through all the mistakes we made, right? We love it when things are quick, not just because we're lazy or we don't want to try something new, but it's an efficiency and it allows us to have room to pay attention to other things. And in an uncertain world, we feel it within us, this desire to be able to check certain things off, say, I'm certain about those, so I can focus on these things that are uncertain. So I would answer your question by saying the things that push us away from questions are also in our nature. But when you look at what questions do, not only for our day-to-day lives and our ability to move forward, but that they actually help the brain stay healthier and accomplish anything we're going to do, I think it's just a call to action to say we should use this capability more than we do and more freely than we do, but not to the exclusion of other things. It's back to that word you put out earlier, balance.

I love your empathy, Larry, and the way we answered that question. In many respects, the restrictions we put, whether it's on teachers or the school board or whoever else, doesn't enable them to ask questions of why are we doing it this way? And in many respects, as you mentioned, we do want to add efficiencies and then we cut out the questioning.

That's exactly right. So if you think about, I'm going to call it the modern corporate setting, and I'm going to give it a generous span in, say, the last 150 to 200 years, which is really quite generous, but let's call it that. That has leaned more and more towards efficiency. Not a bad thing, but more exclusively towards efficiency. The evolution in what's up here in our brains, we're talking hundreds of thousands of years. So it's pretty well set in there. And even though there is not absolute agreement across neuroscience of what's going on in the brain, there is wide and general agreement that the brain is at its best when it is in uncertain conditions, when things are complex, when it's solving, when it feels a sense that it needs to survive, when it is unrestricted, when it is growing in a discovery mode of wanting to find new things. This is just the science. But everything I just listed there is like a guidebook to say, oh my gosh, that's what we have to deal with in an uncertain world like the one we're living and working in right now. Oh, and that's what our brain is built to do. So for me, it's that recognition that says we should tap into that the best way. Possible to use questions to our advantage. These are not zero-sum choices. That we pick this new thing, this guy's coming along, another guy's coming along and saying how important questions are, and we chuck everything else. That's not it at all. It's just saying that the absence of that in today's work and environment and in an environment where AI is becoming much more part of the context and the texture of every work and environment, that's when we need questions most of all. And it's not to say, should we have AI or should we not have AI? It's to say, how do we make this partnership with this technology work the best way it can for what we're trying to accomplish? That's an example of the role of questions.

So in order to do that, Larry, how should I start in this process?

I think the first place that most leaders should start is to quietly observe, as a leader, whether or not questions are being asked in their organization. And if they are being asked, are they really questions? Or are they statements that are being made?

I love the point you made. Whether questions are being asked. What types of questions? How do you know people are really asking questions in this organization?

Sure. And that itself is a good question because there's a whole range, right? If you lay out a spectrum, as I do in the book, just for reference, this is not an absolute, but just to say where questions fall, there's a spectrum that runs from on one end what I call functional questions. What's for lunch? What will the numbers be next quarter? Did we hit them, right? There's a function to those questions that is really after an answer. And then that question is has less return that you get from it once it's been answered. That's on the functional end. Then there are these, I call on the other end of the spectrum, great questions. They're bigger. They're more related to your vision for the organization. They even start to touch on strategy. They're certainly there in the mission. They're open-ended in a way because you find, you say, this is the hill I want to take, this is what I want to accomplish. And then you start asking some functional questions about how do I do it in the immediate, but you're always returning to that longer-term view and that longer-term path. Then there's the stuff in the middle, and I call it the messy middle. And the kind of questions that reside in the messy middle are not just ones that aren't functional or aren't great. They're questions that have not been thought about. So because we don't know if we're using questions in a functional way or we're stretching for something greater, and we just don't take the time to ask, is that why we're asking? We never place them on the right path so that they can have the greatest return for us. So this is why I say even observing whether or not you're asking questions and then observing where they fit on that spectrum tells you a lot. A lot of leaders will look at the questions that are being asked, they'll see that questions are being asked, place them on that spectrum, and see that not many great questions are being asked, right? They're all about the function. In a world that's ever changing, that's a pretty dangerous thing. The second thing a leader can look for without ever opening their mouth is who's asking? Is everybody invited to ask, or is that limited to the C-suite or certain leadership or just the managers? Or does it radiate all the way down to the people who touch the product or the service or the customers most directly and probably have some pretty interesting insights that we all should be asking questions about? So these observations of are you asking at all? What kinds of questions are being asked? Who's asking them? And then underneath that, what's the origin story of all that? Do we have a culture that basically says, without saying it, you're not allowed to ask? Or do we have a culture on the other end that says, I truly want you to be innovative, even if it turns the place upside down while you're doing that? Or is it somewhere in between? Just those alone tell an individual leader where questions fit in their organization. And that's really the answer. Because if I was to sit here and say, here's how everybody starts, right? And this is the path you have to follow after that, it shows that I don't know very much about questions. But if you approach it in the way that I'm suggesting, I think you can learn a lot about what you know, what you don't know, and what you could do.

Now, would that gauge be different, Larry, with respect to the type of organization or industry, or do you see it being relevant in all types of organizations?

I think you could pick an organization or an industry where let's just say things don't change a lot. It doesn't mean they don't change at all. Our tendency is to say, oh gosh, we're an amazingly innovative organization. We should be asking all the time and really pushing that, or on the other extreme, no, we're pretty predictable and we should be pushing towards efficiency. So it's not that those statements are completely wrong, but they say something about the proportion of question question asking that you do and the way you ask questions rather than whether they should be there or not be there, if that makes sense. So I think that does shift across organizations and appropriately, and you mentioned AI in that. The role of AI in any organization shifts in a similar way. It's a tool. It can be a partnering tool, but it's not going to mean the same thing in every organization or in any moment in time. It's a tool that needs to be constantly referenced again to say, what is it we want this to do? How do we want it to help us? How do we as humans want to interact with it? And does that still fit the assumptions and circumstances we're in? Or do we need to change something? That's not really new to leadership or management or anything else. It's just a new thing we're asking those questions about.

So it takes that intellectual humility we've touched on a couple of times. And I think the more experience we gain, the older we get, the higher up people move into organizations. We do accumulate a certain amount of expertise, knowledge, understanding. It becomes harder to maintain that intellectual humility that is required for the right types of questions for us to ask. How do you do that, Larry? You are brilliant, author of many books, Fulbright scholar, you name it. How do you maintain intellectual humility?

Thank you for those very nice compliments. But I will tell you that the more projects I get into, like the ones you described, really the more I understand that I don't know. And I like to learn. So having that base, I feel, is a bit of an advantage that I like to learn. Here's a second thing that I use as a way to practice intellectual humility, and that is to understand that there's a difference between humility as we usually think about it and intellectual humility. So humility is really, it really involves an ability to see your current limitations in this situation and this moment. It's very now focused. And we think of that as humbling in the sense of almost yielding or giving up in the bad sense. Intellectual humility focuses on knowledge, beliefs, intelligence, things that are bigger than this moment. And so one of the ways that I think about intellectual humility and try to embrace it more often is to say, what is this moment telling me about how I think overall? What is this moment telling me about what this moment might mean in the future? And its reference points to the past. So it's even just that distinction between humility, which we think of as meekness, and intellectual humility, which is more growth mindset, is a distinguishing factor that I think we free ourselves to practice more intellectual humility that way rather than saying, oh my God, that's a form of humility. I got to get away from it. But let me give you a couple of others that I found very interesting from some of the interviews I did. One person I spoke with talked about how her signal to herself to regain intellectual humility as a priority is to quiet her cleverness. So it is this acknowledgement that she is unbelievably clever and smart and accomplished and everything else. But the way she can stay achieving at that level is to quiet her cleverness. A second person I talked to said, I try to listen atmospherically. And I love that because it says instead of in a QA exchange where I'm typically waiting for an answer, I ask you a question and I'm waiting for an answer. Or I ask you a question and whatever your answer is, I'm trying to move on to my next question. Listening atmospherically is like taking in those five C's. What is the context in which we're saying these things to one another? What am I trying to connect this to? What could I connect it to? So I love that concept of am I listening atmospherically or am I listening in a very narrow, typical way? And I'll give you one more, and that is to decolonize our thinking. We don't realize how quickly we get down a path to thinking within boundaries. It's not a totally bad thing. It's just something that needs to happen and then needs to open up and then needs to happen again and needs to open up. And when we don't have those opening up intervals, we colonize, we become very close to our thoughts and we put boundaries around them. So if you decolonize your thinking, as somebody else I spoke with said, you're allowing yourself to move beyond the boundaries, beyond the rules, the plans, even the results that you've had, not necessarily to change, but to see where there is opportunity to change or to do better. That's it. And if you think of all three of those things, quieting your cleverness, listening atmospherically, and decolonizing your thinking, you're just playing around. Nobody has asked you to change anything. You're just trying out new ways to see the world and to see your own thoughts. That's intellectual humility.

What a beautiful way to frame it. Because before we follow your framework asking questions, we really need to open up and have that intellectual humility.

Exactly. So this is an interesting thing. That the art of the ask is an overlay to anything else you're doing. It's not a replacement. So you asked me the question about how does a leader, CEO, whoever it might be, begin to do this. And I was thinking at the time about Danny Warshe, his book, which is See Solve Scale. And it's a Bible-like book for entrepreneurs. Danny is a multi-time serial entrepreneur, like successful entrepreneur. And he started the institution at Brown University for entrepreneurship. So he's seen it from a lot of different angles. So Danny has a way that he encourages entrepreneurs to think about how they build their business. This is something that a leader in any position with any type of organization has to think about. And so he boils it down to a framework that has four components. Digest, right? You take whatever's in front of you, the opportunity, the threat, the culture that exists, the culture that you want, and you digest what's there first. That's a big question-asking thing. Then the second step is to aim it. Whatever I've taken in, where do I aim it towards something I can build on when it comes back as something that's worth pursuing, which sometimes that takes a while? The third thing I want to do is embed the behavior, right? If I digested that this is the right thing to aim at and the way I'm doing it is working, I want that to become a behavior. And ultimately the fourth step is to establish a new norm. So what I'm doing is I'm just giving you another framework, right? And I'm not saying that's better or worse than the art of the ask. What I'm saying is the two things go together. And any leader can say, gosh, I work off this framework, whether it's loose or firm. The answer is good. Begin with that and overlay the art of the ask on it. That is more likely to get you to see the truth and then to make the kind of changes you need to make that are the valuable ones we want to make.

And in doing that, I want to wrap up with one thing that's been on my mind a lot as well, Larry. You mentioned that our brain treats open questions like a batch file. And I love that analogy. And therefore, the power of even asking ourselves better questions.

Yeah. So I think of it as your R-O-R, your return on reflection. Because typically, when you're asking yourself questions, you're asking reflective questions. They might be directed towards something, so we think of them more in those terms, but they typically are reflective. And I would start by saying there are those who don't do that, right? They probably have experience that it works, but they don't do it as a habit or as a practice. That's a good place to begin. The second thing, which is even more powerful, is when we reflect on something, we tend to look backwards, just like AI. We tend to look back and reflect on what's happened and learn the better lesson in that context that's already occurred. But reflection can happen forward too. It's a training ground for doing things in the future and hopefully doing things more efficiently. And then when you expand that and into an exchange with others, you amplify that reflection. So it's one of those ways that we can start personally, amplify what we do personally, and then connect it to other people. And I think that's always the best individual exercise.

It is a powerful exercise. And I have to tell you, it's been on my mind the past few weeks after I read your book. You've all known Harari, he is a tiny bit dystopian on AI. And he talks about how his concern is when AI gets to know us better than we know ourselves, and how it will therefore be able to manipulate us. On the other end of it, if we are able to ask ourselves deeper and better questions, we will also get to know ourselves better, achieving part of what Harari says we need to be able to do in order to have more control of our own judgment rather than AI.

Yeah, I really love the way you summarize that. And I'd summarize it down to one word. It's a choice. So it's not a lack of ability. It's not even a lack of know-how about what to do. If you don't like my guidelines in my book, there are others out there that encourage you to ask questions, but you have this choice to ask, to reflect, and to build your knowledge of yourself. AI isn't going to replace us without us choosing to allow it to replace us. That's the ultimate takeaway. So I think we have a little bit of a job to do.

We do. And learning how to ask better questions becomes an essential part of that, Larry. So for the audience to follow you, your work, and find your book, where would you send them to, Larry?

I appreciate you're asking. So the book can be found virtually anywhere. But if you go to my website, LR, those are my initials, Larry Robertson, lrspeaks.com. You can learn about the book, me, get the book, and everything else you probably want.

I so appreciate you, Larry, and your book, Great Question, The Art of the Ask, and Getting More of What You Really Want. Thank you so much for joining me in this conversation, Larry Robertson.

Thank you for the invitation and the great questions.

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