Strategyzer Webinar with Hal Gregersen: Asking Great Questions

Hal Gregersen, who interviewed over 1,000 leaders, argues that only 10-15% of managers ask catalytic questions instead of providing answers. He shares a "question burst" routine: 2 minutes of context, then 4 minutes of questions only, no answers allowed. It produces actionable ideas 85% of the time.
Questions this video answers
September 12, 2019.
November 2018.
Over a thousand leaders ("interviewing over a thousand leaders in depth").
About 10–15% (he contrasts this minority with the 70–80% who are answer-centric).
Explain the issue in up to 2 minutes; then 4 minutes of nothing but questions with two rules: (1) no one answers questions and (2) no one explains why they are asking the questions.
Chapters
Everyone, let's get started. Thanks for joining today's Strat Chat webinar session. We're going to be talking with Hal Gregerson about asking great questions. As always today I'll be your moderator. My name is Kavi Gupta. You can find me on Twitter as AbbyGupta and our host will be Alex Osterwalder, co founder of Strategizer and co author of best selling books Business Model Generation and Value Proposition Design. And like I said, our special guest today is Hal Gregerson, a friend of Strategizer and a friend of Alex's, known largely for his role at the MIT Leadership center, but also for the last book he just released in November of 2018, which is questions Are the Answer. And like I said, that's going to be the main focus of what we're going to be talking about today. If at any point you want to leave a comment or a question or feedback about the session today, you can tweet us RateGizer. Use the hashtag Stratchat. That's how we'll be able to see your tweets. To us, our great colleague Matt is actually going to be paying attention to the tweets going around and he'll be live tweeting the session as well from the Strategizer Twitter handle. We also encourage you to go to the blog strategizer.com blog to check out further content and resources on topics like today as well as other ones around Business Model Innovation and Value Proposition design. Quick note, we've just refurbished the blog and we're very excited to share it with you. It's much more visual and the content is so much more accessible, so please do check it out. I also want to point out that you can visit strategizer.combooks to grab a copy of some of our best selling favorites like Value Proposition Design and Business Model Generation, but also to sign up to receive updates on some of the upcoming releases that we will have in the Strategizer series. You can see two of them there testing business Ideas, the Invincible Company and a couple of other titles that will be coming up. Lastly, if you are a company that's looking for solutions to help your team upskill to validate new ideas to expand existing business lines or launch new growth engines. I encourage you to check out strategizer.com enterprise to see what we offer to the enterprise suite of companies. Or you can reach out to our sales team@salestrategizer.com now. Hal, if I'm correct, I believe you have slides. I'm going to stop the screen share on my end, actually.
I don't have slides.
Going to be a great conversation either way then. Alex, why don't we just kick it off then about why you thought Hal would be a great guest for today's Strat chat.
Thank you, Kavi. And first of all, thank you, Hal, for joining us. Welcome to the Strat Chat.
Thank you.
Why is it a great thing to have Hal? I think that's a question that's very easy to answer because he has such a long experience in innovation, creativity and helping people and companies change, that it's just a great opportunity to have Hal for the first time on Strat chat. So Halloween, I want to kick it off with very simple question. If you want questions is really back to the basics. If you want what got you started on this idea to kind of go back to the basics and say, well, we're maybe not as good as we should be about asking questions. Where did that come from?
That actually started literally almost 30 years ago. Alex. I've lived in Finland, I've lived in England, I've lived in the US I've lived in France, I've lived in the United Arab Emirates. And over the course of a lifetime, living in different countries, you realize that when you drop into a new space, if you think you understand what's going on, you're going to be dead wrong. And that kind of international living and working experience forces someone almost to ask questions they otherwise wouldn't ask. And so the starting point literally was 30 years ago, trying to help companies finish, companies in that situation to go global when 90% of their joint ventures internationally were failing. This was 30 years ago. And the ones that succeeded were led and guided by leaders who were exceptional at landing on their feet in an unknown, uncertain context and asking the right questions to unlock new insights and actions. And then about 20 years ago, it was a deep dive into transformation and change, helping folks like Lou Gerstner IBM move from selling mainframes to selling solutions. And that's a massive shift. It sounds simple to say, but incredibly difficult to do. And again, in transformational change, it was the same story. These really excellent leaders pulling that off were really just as excellent at asking perhaps provocative, energizing questions. And then for the last 15 years, the lens changed from transformational change to the start of change, which is really innovation. And how do you generate innovative ideas? And in studying, literally over the course of those years, interviewing over a thousand leaders in depth, the theme was consistent. All of these Leaders, whether it be change, innovation, globalization. The story was at the very core a skill set they all had in incredible depth was they asked catalytic questions, ones that challenged a fundamental assumption but didn't destroy people in the process. It actually energized them to do something different. So it has a long history, but it has a purposeful story.
So that's pretty counterintuitive. If we want we always, you know, the cliche image of the leader, of course, really cliche, is that leaders have answers, right? And of course, you know, we do know now with all the disruption that's going on, leaders who have the answers probably might find themselves in very difficult situations. But so do you really see this as something that's consistent across, you know, the last 30 years? Or is this something that has, you know, become more important over the last couple of years with the, you know, increase in disruption? Do you see any changes in the patterns? Or is this pretty consistent across the time you've been looking at this particular.
That's a great question. A couple of responses to it Alex. One would be I'm going to go back to my PhD and this was about 30 years ago. I was doing work with some professors who were at the cutting edge of employee empowerment, the big word back then. And one had just finished up a big job in a meatpacking plant where they had tried to transform from a top down organization to a self managed teams, self organized teams leading the organization without bosses. At the end of this three day program, one of the butchers stood up in the back of the room and said, slamming the cleaver into the table, I demand my right to be told what to do and how to do it. I want a manager. I don't want to have to do that work. And it was but two days later I was watching a cartoon show with my 4 year old son and there was a manager, the park ranger and I Yogi Bear cartoon that was telling the bears what to do. And he said he was the manager. And I turned to my 4 year old son, I said Matt, what do managers do at work? And he said they, they throw kids toys away. And we lived in an apartment complex. The manager had a manager tag on the door of her apartment. She hated kids. And every day around dinner time she would clean up any kids toys and throw them in the garbage dumpster. So managers throw kids toys away. So I was like, this is intriguing. How do kids grow up thinking what managers are? So I literally interviewed 500 children and surveyed a thousand and came up with two fundamental images that children grew up with for what managers do at work. Number one, they are like traffic cops at work. They control things. They make sure things are running right, and people do what they're supposed to do. And the second metaphor was managers are like mechanics. They fix things. Got a problem, go to the manager, she fixes it. And both of those images, those metaphors of, you know, being the cop at work controlling stuff, or the mechanic always solving things, somebody else's problem, they are so antithetical in some ways to the innovators that you and I have worked with and studied, Alex, over the course of our work. And what's funny, even though that might sound like 30 years ago to this day, I will ask groups of middle to senior level leaders to draw a picture, literally like they were in kindergarten, to draw a picture of what a manager does at work. And if you content analyze their images in 2019, they look no different than they looked in 1989, which was these scribbled images of managers at work are basically controlling and fixing things. And more often than not, there's a little bubble coming out of the manager's mouth telling somebody what to do, which is what it's. Everything you just described is this stereotypical image of what managers do at work. And tragically. Well, we'll stop there. But you get the story. You know, we. Even though. Even though we tout innovation as a way that we should be doing things, and it's the way to the future, most people I deal with, most organizations that people work in, they have managers who are all tail and no ask.
So that's pretty amazing, right? Because that is kind of a contradiction between what people think management is and what you just said before. You're finding in the patterns of good leaders, right? So there seems to be a tension there between the cliche that we still kind of see as what managers do and those that really perform who seem to be asking the right question. Does your research over the last 30 years show that tension a little bit between the perception and the reality of good management?
Yes, in the following way. So I like you, more recently in the last decade or so, have paid careful, deep attention to the most innovative leaders. These are the ones who not only ask questions, but they do something about it to the point that those questions lead to insights that are valuable. And so when you look at those folks, they recognize the tension, but they transcend it because they build organizations where that tension is resident, where they create an environment, a space, a culture, you know, whatever you want a word you want to use where fearless questions can flourish, where people can ask the tough questions. It's the way, it's simply the way in which they go about their work. Now that's the 10 to 15% literally of the leaders on planet Earth. I'm not sure what it's like on other planets around the world out there, but on our earth it's about 10 to 15%. And you know, for the other 70 to 80% of leaders in most organizations, they're answer centric. And the fun way that it's fun and tragic in some ways to look at these patterns and how ingrained they are and you know, an invitation I make often to people is do a question audit in the next 24 hours. In other words, track your questions. How many are you asking, what kinds of questions are they, how are people responding to them? And conversely, who is asking you questions and how are you responding to them? And after they do that 24 hour audit, most leaders are quite surprised at either the lack of questions or the simplicity of them. And then I asked them to do a life history audit of questioning. So go back to when you were in your home growing up. How did authority figures respond to the questions you were asking? What about when you were in primary and elementary school between grades K through 12, roughly, how did authority figures respond at school? What about your college and university work? How did authority figures, professors and teachers respond to your questions there? And what about your first professional position? And then now look at your question audit from the last 24 hours. And what does that pattern look like? And what's really striking, Alex, is that there are powerful forces at work from birth forward that go over time to shut down and close off this natural inherent corporate questioning capacity we have as human beings.
Wow, that's amazing. So much in so little time. So I want to go back before I get to culture and even, you know, the individual aspects of the forces that are at work that lead us to ask questions or not. I want to go back to something pretty simple. You know, people like to say there are no such thing as dumb questions, but I'm sure there are some better ways or not so good ways to formulate a question. And, and Cyril, one of the listeners is asking, is there some kind of framework or tool way or there's some kind of tips that you could give us to ask better questions?
Well, I am allergic, I am reactive. I am hesitant to ever give toolkits in a really specific way. Now having said that, that's my disclaimer. I now I'm going to give a tool that I discovered 20 years ago in the middle of a meeting with a group of leaders. This was 20 plus years ago, trying to figure out how do we create greater gender parity in an organization. And so we were stuck on the issue. The energy in the room was low. People were, you know, like, can we leave now? This is not going anywhere. And I had been doing some reading and deep thinking and actually had been in a conference with Parker Palmer, who's an amazing educational philosopher and does great work in terms of the world of education. Anyway, his world is questioning and inquiry. So we're stuck. Energy level low in this group. And I closed my eyes and I said, what do I do here? And it's like, just stop. Ask nothing but questions about this issue at hand. So I opened my eyes and I gave them two rules. Number one, I told them the deal. We're going to ask nothing but questions here. And here are the two rules. Nobody can answer any of the questions and no one can explain why they're asking the questions. And those two rules matter deeply because when we answer questions and when we explain why we're asking questions, we are putting filler material before and after the question that actually keep us from getting insight. And so it's literally, it's literally stripping out that filler material. No answers, no explanations, and just dropping questions into the conversation space. So we did that for 10 or 15 minutes. This was the day of blackboards. We filled up these blackboards with dozens, if not a hundred plus questions. The energy level in the room, Alex, went from low to high in terms of negative to positive. We had started to reframe the way we were seeing this issue in ways we'd never seen it before. And we had a number of ideas that could potentially change the way we could approach things. And at the end of that, I'm like, what just happened here? And then I thought about it, and I've since refined it. I call it a question burst. So there's my method for the day and what I've discovered. I've collected data from several thousand leaders doing this process I just described. And it's literally, you're stuck. You've got an opportunity, you've got a challenge. Explain to somebody else. I need your engagement. I need your questions to get unstuck. Here are the rules. I'm going to spend two minutes explaining what my issue is. Because if I spend more than two minutes explaining the issue, I over analyze it and I overfill your head with information. That's already stuck in mind and then you're stuck just like I am. So two minutes, maximum explanation, then we're going to set a timer. Four minutes, nothing but questions. And with the rules, no answers, no explanations. And then we do it. We, we just generate those questions. The data would say we'll get 15 to 20 questions in those four minutes. And then you've got, at the end of the four minutes, here's what the data also tell us. 85% of the time we reframe the challenge. 85% of the time we're in a much better emotional place, more positive. And 85% of the time we have at least one new idea that will take us forward. And all I know is the data deliver in that these question bursts don't or they rarely solve an issue, but they consistently help us make progress on the issue. And that's what questions are about.
Wow, that's amazing. So that's a perfect process to help with the problem solving. Again, not maybe with a goal of immediately solving it, but framing it differently, seeing different perspective. That's pretty amazing. So what if we take this and kind of scale it up now to a company level, small company, or even a large corporation, then it becomes culture. How do you design this into the DNA of a company? What have you seen, looking at those companies that do ask those uncomfortable questions systematically, what did they put in place? What were the enablers that they put in place to just have this in their DNA? Right, because culture doesn't just happen, it comes from somewhere. So what did you observe?
Oh, absolutely. So Ed Catmull, who's one of the co founders of Kickstart, the animation studio with 20 plus blockbuster movies, he every day wakes up wondering how can I create a culture where we can be sustainably creative and innovative? And part of that is creating a space where people can ask the tough questions. And so the logic of someone like Ed or Rose Mercario at Patagonia is the how do I create conditions within my organization where people can be systematically wrong instead of right, uncomfortable instead of comfortable and reflectively quiet? And when those conditions get created, people being wrong and uncomfortable and reflectively quiet, if those conditions are present in a meeting, in a room, in a context, there is a super high probability that people will start asking questions they otherwise wouldn't ask. That's the theory, Alex. That's what this research of 200 leaders like Rosemarcar of Patagonia, these interviews delivered basically was that set of conditions, they create them. So if you happen to Work at Amazon and you work with Jeff Wilkie who runs all of consumer worldwide for Amazon. He's the CEO of that seg, biggest segment of the company. You've got this leader who comes into the room with you and he has a mindset of, okay, I've got a mental map of the world and what in this conversation is going to signal that, which part of that map is wrong? He's looking actively for what's wrong in his head instead of what's right. That's a unique way of approaching the world. And then within Amazon at a cultural level, they're a reading writing culture where if you and I, Alex, were on a team and we saw an idea for a better organizational approach or a better product or service for the client customer, we would create this, we would engage in this working backwards process where we'd write up a document. It's a writing culture where we would write a press release. Five years from now, here's what's going to happen. This is how we got prime now, instant same day delivery. Someone, they had the idea, wrote it up in, you know, five years from now we're going to be able to same day deliver items. Then it's like six pages of Q and A questions and answers about this particular idea. It's a written document, five or six pages. People will come into a room and they will shut up. They'll be given that document, they'll be quiet, they read it, they're reflective, they're generating questions, they're generating ideas. And then at the end of reading it, 15 or 20 minutes later, and it's the first time they've read it. Then it's like open territory with the trust based foundation that we're here to make this idea better, not to go after the people delivering it. And it's tough questions, it's good insights, it's tough insights, it's all sorts of feedback. But it happens over and over. They've created a space where people can be wrong and uncomfortable and reflectively quiet in order for new questions to surface to be able to deliver new answers. So Jeff Wilkie again reports directly to Jeff Bezos. He's at the top of the organization. He himself sits 100 plus of these working backwards meetings. It's 100 different ideas over the course of a year. So here you've got an organization that is systematically moving into new territory with different business models, leveraging off of their platform. They've got a process that literally puts people in these conditions of being wrong and uncomfortable and reflectively quiet that generates questions they otherwise wouldn't get and conversations they otherwise wouldn't have in order to do things they otherwise wouldn't do.
Wow, that connects really with. It sounds like it connects really deeply also with the work that Amy Edmondson does around psychological safety, creating that space where people can actually work in a way where they don't have to fear that whatever they say today or whatever they ask, you know, good or bad, kind of backfires. Somebody's asking here from the participants if there are moments where actually it might not be the best thing to do, to ask questions. Have you ever seen situations like that where you would say, look, questions are very powerful and many situations that's the thing to do, but there are situations where maybe it's not the best thing to do. Or is that, does that not exist?
There is some really interesting research that came out of Harvard Business School recently where the common idea you're trying to get things done, you ask open versus closed questions, for example. And you know, historically I've been a little bit more on the open versus closed side, but there are moments where closed questions are really important. When you need to find something out, you ask a closed yes, no question. And so there are spaces where that matters and there are times in which one has to be very directive. So you, I think you know, Ag Lafley, who is two time CEO at Procter & Gamble, and I met Ag Lafley before he ever became CEO. And he did, he did what he did as a CEO before he ever became the CEO. And he did it when he was a young manager in Japan, long before he became CEO, which was he was actively seeking passive data over and over about what could be new, what could be different, what could be better. And so he would regularly in the retail world, he would go into stores to answer the question, how are we delighting consumers at the purchase point? Then you go into homes afterwards. How are we delighting consumers in the use of our products? And very few leaders spend their energy in stores, in homes trying to answer those questions in these sorts of organizations. Now that's AG Lafley trying to push the edge of innovation as the leader. A large, huge, ancient organization, but very successful. But you've also got the other side of AG Lafley, which is, he said, you've got a strategy. You've got to also have a, you have to have a Sesame street simple message which is an answer. It's like, here's where we're going, here's where we're going. I Mentioned earlier, doing some work with some colleagues for a number of years with IBM and that transition from selling mainframes to selling solutions. And at the end of Lou Gerstner's tenure at IBM, when he finally left, someone asked him, why did you leave? And one of the reasons, it may sound silly was he said, I got tired of saying solutions, solutions, solutions over and over and over. And Lou had to have an answer direction, which was solution, solution, solution. He said it repetitively was not in question form, but it was trying to give direction, but at the same time in that direction, giving space. If we're not perpetually actively seeking information at the edge of our system in order to figure out what's the new learning curve, what's the new next new, we're setting ourselves up for failure. So to me, it's not a question of is it only questions or only answers? Because there are moments, and I just described, where answers direction can be very powerful. But here's the context that matters from my perspective. When we are operating on the edge of uncertainty, when it's unclear, given our experience, history, context, what's going on here and what to do on that edge of uncertainty, questions are the answer because there are no answers sitting there. Questions are the by which we move across the horizon into a potential answer space. And that's the quickest way to get there. When uncertainty rules, holding tight and seeking first answers actually can be counterproductive, right?
So the more uncertainty we have, the more important questions are because there are simply no answers, right, that are already there. So asking questions is the only thing you can do. I want to ask you one question here. I don't know. About two years ago, I was in a workshop with Alan Mulally, who turned around Ford, and he was sharing his kind of life lessons. And one of the things he said was, sometimes as a leader, when you're the boss, it's better actually to shut up because you might be trying to add too much value. And what he meant with that was, was that sometimes when the boss makes a suggestion would be more the answer or asks questions, it can almost derail what the team does in the sense that they will see that as the direction that they have to take. So they won't see the boss's question as one question among others, but they would almost see it start interpretation. And what does this mean? Have you seen that danger happening as well? That sometimes, you know, even as powerful as questions are, that when you're the leader, sometimes it's better actually to not ask questions? Because you might derail the team because you're a leader.
I would take a slightly different angle on that, Alex, which is that it's not. It's not that it's better to not ask questions. To me, it's a question of timing. And so that reflectively quiet condition that I talked about a few minutes ago is, let's say I'm either the supervisor or the CEO, and I walk into a meeting of people. My position, by definition, sucks the energy out of the room. If I let it, the position does. And so I've got to not let that happen. And often it could be in a meeting context, especially in a situation of uncertainty. We're trying to be generous of some new ideas and perspectives. I'd be much better off shutting up at the start of that meeting. I'm trying to create a safe enough space. And I love Amy Edmondson's work in the Fearless Organization and her psychological safety work. I've got to realize that I'm walking into this space and the fact. So let's pretend I'm the person who's that. So I. I'm Hal Gregerson. Let's say I'm the supervisor of the CEO. I got positional power. I'm white, I'm male, I'm older. I have a deep voice. And all of those things are conditions that would cause, in some settings, people to shut down. And if I'm not aware of the context I'm carrying into the room, I could quickly squash the questions that could be crucial to unlocking a new direction. And so I come in aware of what I'm bringing into the room, but I'm intentionally quiet and reflectively so. And that means I don't necessarily ask the questions at the beginning. I'm creating the conditions for others to maybe do that and for me, Hal Gregerson, to be uncomfortable and dead wrong about something.
Something.
That's the starting point.
Excellent. So it's not just the question itself. It's really the timing and very powerful, because sometimes we have these burning questions on our mind and we think they're so important that we're actually going to try to put them out there as fast as possible. Whereas, depending on our role, we do need to take care of the timing.
Very powerful.
So you are giving us a couple of tools and tips here that will help us ask better questions. I want to go back maybe from the organization and from leadership to the individual in general. I found question audit such a powerful thing, what you just said, right? This awareness. Okay, how many questions do I ask. What type of questions do I ask? Do you have other tips, you know, for individuals from whatever organizational part they are from, or even as individuals to just start getting better at questions, you know, beyond, okay, go out and do it. What would your tips be to, to train just like somebody trains a basketball or tennis to become a Roger Federer. How do you train to become a better questioner?
Well, there's Questioning 101 and there's Questioning 501, University Cord's Logic. And the beginner based questioning logic is I may not have at the moment what I call a catalytic question, which is it's one that challenges a fundamentally false assumption and gives us energy to do something productively about it. I'm at the starting point, I'm trying to figure something out, or I'm trying to figure out what I'm going to figure out. It's either finding or solving problems. And so at that starting point for me, I may well rely on somebody else's set of questions. So it might be simple as what's working, what's not, and why. Those are fundamentals. But you and I both know, and folks on this, on this webinar, they also know that asking those questions what's working, what's not, and why is one thing. Getting an honest answer is a different thing.
Right.
But that's the starting point. What's working, what's not, and why. And then once I get some data around that, that's more than just what's getting shoved at me. But I'm up, I'm out, I'm in the world actively trying to get answers to what's working, what's not, why? I'm going to start then getting questions like, well, what if we tried this and how might we do that and why not this? And those are more prescriptive questions about how the future could be different. That is a very base set of questions that could be super helpful. Or maybe I'm trying to basically figure out how do I, how do I develop my people better and coach them better. And so in that case, it could be that I go to Michael Bungie Stanier's book about the coaching habit and I grab his powerful seven questions. I mean, these are really, really, really good questions he's got. They're starting points. And then, you know, from that I get up, I get out, I get into the world and I personally and systematically start creating conditions where I am wrong and uncomfortable and reflectively quiet. And that's the next step. So it's partly, you start with this base set of questions, step one, then you get out and engage with the world. And so David Neeleman, who found the JetBlue in the US and then he founded Azul Airlines in Brazil, and then he bought a major share in TFE Airlines and Portugal. And now he's starting another airline back in the us and at any given week, as the president, CEO, founder of those airline organizations, David is doing the following. He's throwing bags into the baggage hold of the airplane with the baggage handlers. He's at the check in counter checking in happy and angry people on a regular basis. He's in the airplanes passing out drinks and snacks. He's in the airplanes when they land, cleaning up the toilets and vacuuming the floors. How many CEOs of airlines do that? Not very many. But what he's doing is he's out there actively seeking passive data by engaging with his organization. And then other people start asking him tough questions, why are we doing it this way? Why don't we try it that way? How do you explain this? Sometimes it's awkward and he's uncomfortable. But that's the way in which David starts to ask questions other people don't. And he's built some of the most successful airlines by financial and service metrics that are on planet Earth. So then you want to then take that base set of questions, get out in the world in conditions where you're going to be wrong and uncomfortable, and then turbocharged that whole process with this question verse process where over and over engage people in the short four minute exercise of generating nothing but questions about the issue. And what that question burst does is it not only helps us generate better questions, but people are more committed to my challenge if they've given me questions instead of solutions and answers. So pretend I come to you, Alex, and say, I've got this problem. What do you think I should do? And then you give me the answers versus I come to you and say, I got this problem. And I'd love to hear the questions you would ask about this problem at the end of that process. If you've given me questions and engage with me, that way you have a deeper commitment walking away from the conversation to help me do something about it. And so questions not only help us get to the better answer by asking better questions, but they also engage people more fully in trying to do something about the questions.
I like that you referred to the coaching habit. Right. It's a different style of leadership, you know, giving direction and only answers or asking those powerful questions to Move your team and almost, you know, kind of guide them in the right direction which they're going to figure out because probably as a leader you don't know anyways because you can't know all the answers. In particular, when it gets a bit more technical, one of the things you say often is I heard you say, you know, getting into this uncomfortable context or you write sometimes embrace the awkwardness. Is this something that you systematically see with some of the innovation leaders that they actively embrace this awkwardness and actively get into uncomfortable situations where they have to ask questions or they get asked questions. Is this a pattern that you've seen more frequently with some of the top leaders that you've interviewed?
Well, with Marc Benioff who's a co founder of Salesforce and now co CEO, we forget that. Here's this guy who's now in his late 50s. He used to be young, he used to be in his early 20s. In fact he went to college like the rest of us, many of us did. And at the end of that he gets this first job where he's selling large enterprise level software for Oracle for 10 plus years and he's incredibly successful at it. But in that sales role you're actively seeking passive data. You're actively on the edge of the organization getting booked good and bad feedback. And I bumped into Mark a few years ago at the Davos meeting and I asked him how do you ask better questions? And Mark looked me right in the eye and he said listen. And then he was really quiet looking at me and I almost started to ask a different question, but I realized he's watching. And then I realized he's trying to figure out am I really listening. And so I shut up. And then we had a 15 minute conversation about what does it mean to listen? Well, imagine that sort of an approach. So here's the other part. Many senior leaders, many strategy makers have a ring of steel around them. Once they get to the top of the organization, you know, they're wandering through the Dabless meeting or they're wandering around the organization, they have a chief of staff, they have other people who protect them from getting uncomfortable information. You and I have seen this over and over. You watch this happen. I know you too. And so if you bump into Mark, there's a high probability he will have no protector around him. He's got no bodyguard for ideas. It's not about physical protection, it's about there's no one there to protect him from information that's going to surprise and make him feel Awkward. So Mark, then he leaves Oracle, frustrated in part about the lack of applicability of large enterprise software to medium and small enterprises. He then goes on a listening tour talking to people around the world, rich, poor, old, young, big, small businesses, religious, government, business leaders. And at the end of all those conversations, he finally lands on a question that's catalytic. What if we sold enterprise level software like Amazon sells books, which people thought was idiotic because they had not done the homework market done for a decade plus? Questions are quests. He was on a quest to figure something out and he got to the question that was catalytic. That was the answer as well as a question. So then I'm going to fast forward real quickly here, which is it's, you know, 10, 15 years and Salesforce is incredibly successful. How do you keep creating these spaces where you, Marc Benioff, get uncomfortable information? Well, number one, all of their strategy meetings, transparent. They are sent across the organization. Anybody can watch those meetings and have input on. That's really unusual. And then the engineers in his organization early on started this chat group to just solve engineering problems. And in some ways it was a grievance space. They called it the airing of grievances chat room. Then it spilled outside of engineering across the organization. And a few of the senior leaders saw this and they're like, we need to shut it down to get. Because it's so raw and transparent. What if people saw this outside of the organization? And then Mark didn't know this was happening and he happened to hear about it in a meeting and he said, put it up on the screen. This airing of Grievances. I want to see the live stream of what's going on. And when he saw it, he's like, there's no way we're shutting this down. This is the life beat. This is the heart blood of the organization and it's telling us what we're doing right and wrong. And Mark to this day sometimes pulls that live stream arrogant grievances up on big sales calls about the value of transparency within the organization. So, you know, what I'm trying to say here is here's someone who has all the reason in the world to walk away from discomfort and be comfortable, but instead has made a calculated choice to step in the discomfort, be it within Salesforce or even beyond, as an activist CEO taking on bigger issues beyond his own corporate boundary.
That's pretty incredible. And it makes me think almost that if we create that transparency and allow people to ask questions, we give the company a more human face. Right? We don't try to put up a facade where we know everything, everything's perfect. We show the inner workings of an organization. So that's one example of a leader trying to make things a bit more systematic. So I'd be curious to hear from you. Have you seen leaders, you know, some of them just do it naturally? You were talking about Pixar. Okay. That's part of the culture that was built up over time. Have you seen leaders that tried to turn around organizations to bring questioning into the organization more sustainable systematically, in a place where it might have not existed before, like at Pixar? It might have been part of the DNA kind of from the start. Have you seen this kind of turnaround happen? And what did these companies do to achieve that turnaround?
Well, Intuit Financial Services company that was one of the founders of a very simple, understandable, intuitive interface to do your personal and then small business financial practices. It was a software incredibly successful, founded by Scott Cook at the height of success. And then it started to decline on its innovation capability. And it was going down and down and down. And at the same time that was happening, Scott Cook would be walking into the CEO's office of Brad Smith. And Scott is a very observant person. He would see like 15 things to fix it into it to make it better. They were legitimate things to fix. And so he dropped this list on Brad Smith's desk and Brad would say, thank you, I'm going to work on it and add it to my other 25 things, and we're going to keep at it. Well, here's the moment of truth. And this is really unusual for senior leaders, especially a chairman of the board. They actually did 360 leadership feedback, not just on Brad Smith as CEO, but on Scott Cook, the chairman. And Scott got feedback that said, guess what? When you walk into Brad's office and other people's offices and you drop these lists of arguably good ideas into their workflow, it actually has a lot of counterproductive elements to it. You're complicating things in ways that are just not helpful. Now, Scott's rich. He's the founder. He's got every reason to not listen to the data, but he does. He then chooses to engage with an executive coach. He works on the issue for a couple of years. And now I'm going to tell you, here's what the conversation looks like. When he changed. He'd walk into Brad's office, then he'd say, hi, Brad, what are you wrestling with? And then he'd shut up. Wow. And Brad would tell him, you know, and it's a really important thing. Wait time is important. What are you wrestling with? If they really have a tough issue, it's going to take three to five seconds before they respond. And most managers want answers in one to two seconds. Give people wait time. So it's what are you wrestling with, Brad? Wait time. Thousand one, two, three, four, five. It's in those last two or three seconds that people realize you might actually be interested in the real issue. So then Brett talks to them about the real issue. And then he. And then Scott at the end of the conversation asks another question. How can I help? Conversation over. What are you wrestling with? How can I help it? Start at the top. Brad then realized this is powerful. He started doing the same thing with his direct reports. They realized the power of it. They started doing that with their direct reports. It was a piece. It was a single piece, but it was a piece of an innovation trajectory that literally was going down by an innovation premium metric. And it went back up over the course of the next five years. But I think part of it was that simple but significant piece of the puzzle.
Shows the power of questions. Absolutely. One thing I think what I heard. Just want to go one step back to Marc Benioff's question about basically was a powerful question, a very fundamental question about the business model. And here is what you were just describing with Intuit was very powerful question around how do we interact in a management relationship? Do you see a back to basic, very fundamental questions that some leaders might even be asking, hey, how should we organize? Do we stop using the traditional hierarchy? Do we distribute power A lot more than we've done so far, so we're ready for disruption when, when it happens. Are you seeing a trend towards some of these very basic and fundamental questions? Questioning the business model, questioning the management system, that might lead to some more fundamental innovation than what we're seeing so far around product innovation. Is that something that you're seeing emerge or is that just in my mind trying to see patterns that might not be there?
Well, great question, Alex. At a broader level, I'm working on a new project called Leadership in the Age of Outrage. And we live in a very different world today where both inside and outside of organizations, we are being pummeled with questions and concerns and issues that otherwise were not. I was recently talking with a group of CEOs about what are they sort of most attending to. And a big issue for them is politics. And it's not just government politics, but it's is the politics of this very complex, uncertain world we're walking into. At that level, then you've got sort of the next level down. Digital transformation is a fancy word, and AI is equally fancy. But at the end of the day, it is transforming not only what we do, but who we are. And so you've got senior leaders in organizations responsible for strategy who are being challenged both from digital work transforming the way they approach the world, to the.
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