The Pursuit of Transformational Change with Ron Carucci and A More Beautiful Question with Warren Berger

You wouldn’t know it but even leaders can be terrified of asking for help. With their position, they are expected to know everything and they’re supposed to carry everyone on their backs. So when they ask for help, the misconception is they are lacking and also not confident. Ron Carucci believes that these are actually the leaders to look for because they are in the pursuit of transformational change. He explains that people rise within the organization because of their technical skills and emotional quotient. Questions lead to innovation. This is why kids today seem to know a lot of stuff. Questions help shape the way we interact with people. However, as we grow up, this way of communication becomes difficult. Warren Berger explains the importance of questioning in leadership and in relationships.

TTL 182 | The Pursuit of Transformational Change

We have Ron Carucci and Warren Berger here. Ron Carucci is the managing partner of Navalent and he’s a seasoned consultant who has more than 25 years of experience working with CEOs and senior executives. Warren Berger is an author specializing in innovation, creativity and questioning. Between the two of them, we are going to find out a lot about how organizations can improve.

Listen to the podcast here

The Pursuit of Transformational Change with Ron Carucci

I’m here with Ron Carucci, who’s the managing partner of Navalent, and a seasoned consultant with more than 25 years of experience working with CEOs and senior executives of organizations, running Fortune 50s to startups in pursuit of transformational change. His consulting has taken him from to more than twenty different countries on four continents, and he’s consulted some of the world’s most influential CEOs and executives. It is an honor to have you here, Ron. Thank you.

Thanks for having me.

I was watching your interview with Jeff Hayzlett, who I’ve had on my show and he’s a great guy. You do work with the C-Suite executives. His group is an interesting group because you get different perspectives from all the different specialists and consultants out there. When I was listening to your talk with him, it was bringing up some of the things that I’ve talked to other leaders and coaches on my show. How many leaders don’t feel like they know what they need to know it, but they don’t know where to go for help? What do you do for somebody like that?

I’m always grateful for somebody who at least is going to acknowledge they need help but they didn’t know where to get it or what kind to ask for. That’s always, for me, a great step ahead of the game. If you’re a leader, you need help. Those that want to go alone and who believe that they’ve got it all together and don’t need the advice, that’s the dangerous leader. That’s the leader to avoid especially when you’ve arrived at a higher opportunity in an organization where things can be very disorienting. I hear it described as an alien in a foreign planet when you get up there because the political currents are different. The rules are different, the relationship dynamics have completely changed, your time horizon for how you can achieve results has elongated, and so all that disorienting material when you get up there can be unsettling for leaders.

Just normalizing that, that’s the case for everybody who arrives. It’s necessary to talk about it with somebody and ask for help. Once you decided you need it, finding credible and experienced people, whether they’re people who’ve been in those shoes before, who you trust, or people who advise people in those positions or just plenty of great reading material out there, but do something to take to get inside your own head and disconfirm your own choices because at that point, most of the conclusions you’re drawing are probably not reliable. Disconfirming data and getting a broad level of protected from other places to help form your choices about what to do next, that’s important.

A lot of us don’t know what we don’t know. You’ve worked with so many industries from health sciences, biotech, consumer products, retail, and food. Each industry is so unique, but every leader is so unique. I wrote my dissertation on emotional intelligence. It was something I saw a lot of leaders had issues with. Do you run into a lot of leaders that you deal with? Maybe you need help with their levels of EQ?

I don’t know what leader that doesn’t apply this. I’m building my next article on the dark side of emotional intelligence. We portrayed the workplace with a great deal of good information about relationship intelligence, RQ or EQ. Being self-aware, being self-regulating and phatic, having good social skills and being good in listening, the consciousness has been raised, but what those things actually look like in real time and whether you’re any good at them or not, I still think that’s the gap. Many leaders rise to the top of their organization because of their technical skills, because of the results they’ve achieved, and because of their relational capability or their EQ. Some really smart folks making decisions about succession recognize that with this ability to build deep and interesting connections with others and influence them very well was important.

Those leaders did that but too often that’s not one of the criteria or the gravy. “They’re very smart and people liked the message that I did,” but it’s almost not the fundamental criteria for advancement, and that’s unfortunate because at the top of an organization, garnering the ability to build important and reliable connections with your peers and your direct reports and your bosses is so fundamental and it’s one of the major derailers to most leadership careers that are otherwise very promising. People get to the top and they are a relational nightmare and they don’t even know it. They don’t even realize that people are backing away from them and withdrawing support, because they can’t see it.

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The Pursuit of Transformational Change: People get to the top and they are a relational nightmare and they don’t even know it.

It’s interesting to talk about the things of why leaders fail. Sometimes it’s the Peter Principle, someone’s value keeps getting higher up and you finally get to the point where you’re not meant to be where you are. How often do you run into that, or is it more that they just need help?

When we hear, “They weren’t a good fit,” almost always that’s never the case. From our ten-year study, we’ve learned that more than half of executives appointed fail in the first eighteen months of their assignments. It’s almost always an unnecessary failure. It could have been anticipated, but this is a great example about how we often set them up to fail. In the selection progress we’ll say things like, “Look at the great brands you built in your other organization, that’s what we need,” or “You’ve turned on to other supply chains. We need that here,” or “Look at these great technologies you’ve advanced in those companies. That’s exactly what we need here.” In that message we said to them, “You have a formula, you have a recipe for success and we need it here.” We’ve given them permission to ignore context. We’ve given them permission to be relationally toned down. We said, “In here, and just slap on your recipe.” When they do, they we’re shocked when it doesn’t work. When they have not adapted, when they’ve not read the context as well, when they’ve not thought about what wisdom can they bring here and realize that the context has as much to change in them than they have to change in it. We give them a hall pass to skip past all of that. They just come in here and start slapping on. When it doesn’t work, they slapped harder, and the harder they slapped then we get the, “They weren’t a good fit.”

It is interesting to see what’s transferable and how much context you need. How do you define failure in that?

They’re no longer in a job, not by their own choice.

What made you look at that particular timeframe? What happens after eighteen months, and what else did you find in the study?

We got to use some great AI analytical tools to look at the data. We isolated a hundred leaders to understand what were the landmines. We’ve known for twenty years that more than half fail. It has been true for twenty years. It depends on whose research you conduct to. Ours was in the mid-‘50s, but there are some studies that say it’s as high as over 60%. Between 40% and 50% has been the norm for twenty years. When they started to become our clients and CEOs are calling me and saying, “I pay you help this guy? What’s going on?” It became personal. We thought, “How is it that we’ve allowed this level of carnage?” You think about the damage to careers, to opportunities, to families who will be relocated, to people who are in the middle was seen as high potential and all the bells and whistles that come with them, they’re a bag of chips. Then one level higher suddenly it’s disaster. Why hasn’t anybody before now said, “That doesn’t make any sense?”

For us, we can do better, and we have to do better. We began to unpack what could possibly be going on here that is setting these otherwise very promising women and men up for the disasters. What was exciting about the research was that it will isolate four very recurring patterns. One of the questions we asked was, “What’s the other 50% doing? If they’re sticking the landing and sliding once in a higher altitude, how are they doing it?” We were able to isolate four very recurring, very clear choices that they made that not only made them thrive but highly influential in their organizations. The problem with the data was no matter how we cut it, and even after 99, my research team did 99 different personalities. They finally said, “Not enough, it’s not going to change.” The issue for me was there had to be all four. You have to do all four then that puts you in the group. The bar is too high. How do you tell people, “Be perfect?” The best part of what we discovered was all four of these patterns, you can learn. They are things that people acquire along the way. If you wasted your first assignment as a vice president, probably not a good idea, but they can be acquired.

The first one was called context. They could adapt. They were curious, they ask questions, and they try to understand the environment before they impose their ideas. They didn’t start with start with, “I have an idea you need or I have an answer to a question you may not be asking.” The successful leaders started by wondering and asking questions and figuring out how do they adapt their ideas and their approaches. The second one is breadth. These leaders understand that if they rise up in organizations, their job is to integrate cohesion. If they’ve grown up in marketing, obviously they see the world through the lens of the consumer. If they grew up in finance, they can see the world through economic lens. They need to see how all the pieces of the realizations fit together. You can look at the seams of the organization where value is actually created and stitch both teams together and create a whole from the parts. Too many leaders get up there and they actually remain so narrow in their views they actually make the division and fragmentation in organizations. They make it worse.

The third is called choice. These are the leaders that could make difficult decisions. Committee leaders get up to the top of the organization and are so focused on buying well or pleasing people. They do way too many yeses, and they dilute the focus of their organization. Successful leaders were able to narrow the focus of the organization by saying no. They were comfortable disappointing people if they had to, for the greater good to prevail, so that they could keep people narrowly focused on a few choices to be successful rather than trying to make everybody happy and do it all. The last one is connection. These people had phenomenal relationship with bosses. They were trusted, they were credible, and the key differentiator was they were seen as trying to make other people successful. They prioritize their stakeholder management by people whose agendas they could help advance, not who they get something from. You can see four high bars and to be effective at all of them is not an easy task, but if you think about failing three or four of them, you can see why the failure rate is so high.

The first one you mentioned was curious. I’m writing a book on curiosity and the importance of it. Do you think you can develop that in a leader? Does it come naturally? A lot of the people I meet who are successful, that’s one of the words they use to describe why they think they’re successful. Why do you think some people need help in that area?

As you rise up in your organization, you unfortunately lose your capacity to be naturally anthropological. Leaders who are predisposed or too gratified to being an answer ATM rather than a question asker, yes, I do believe you can cultivate it. You have to put them in an environment outside their comfort zone and put them in places where are naturally unfamiliar to see how they thrive. Because if their natural instinct is to reach back for answers or approaches that are used in the past, try and take the unfamiliarity and impose on it my certainty that tells you they’re probably going to struggle. If they, in a controlled environment of unfamiliarity, are willing to suspend disbelief and actually adapt and be okay with discomfort and ask different questions, that’s going to tell you that they’re going to be able to adapt. You can cultivate that ability to be anthropological, to be naturally fascinated, to ask them specific questions. Some leaders have to say, “Here’s the list of questions you have to ask before you can make any declarative sentences in this meeting.” You have to mechanize it sometimes but people can learn it for sure.

I’ve worked on several boards of advisors. How important is it to get people to advise you that are outside of your industry to give a different perspective?

There are two sides to the story. There’s this more innovative novel out-of-the-box thinking that might come from somebody off your context, and then there’s, “I have enough knowledge of your environment and I’m going to give you credible advice.” Every leader has a personal kitchen cabinet where they have one silver bullet advisor. Every leader, especially toward the top of organizations, ought to have a variety of folks from whom they draw advice and from whom they are constantly and actively seeking and just confirming data. You should always be looking to have people who will test your assumptions, to just to poke holes in your thinking. For me, whenever I take on a new executive or CEO to work with, my first question is I want the name of your therapist, your nutritionist, and your trainer. The four of us are going to work in concert. We’ll go ahead and build on four or five other folks in a variety of context that you can draw advice from. This is your core team. If you haven’t got someone caring for you, physiologically caring for your emotionally and psychologically and caring for your health, then you have no reason to be asking me to care for your leadership.

I interview a lot of people about coaching and mentoring and sponsoring. How does that apply to leader? Do they know where to get the mentoring and the coaching and the things that we expect for lower levels?

So many leaders think that when they get to the top, they’re done. They have arrived. They just assume that if you arrive into any broader assignments thinking, “This is evidence that I’m finished.” It’s highly likely you will fail. That’s when your greatest disorienting starts. The notion that having a coach is a sign of weakness or a sign that you need to be fixed or repaired in some way or be defective in some way is so false. I hired my own coach three years ago. For me at this point in my career, I thought I’ve got to start taking my own medicine here. It was one of the best decisions I made. After 30 years, and it’s not that I’m calibrated for that long, but to be intentional about calibrating and find my own influence in the world. All of us should have some source of eyes on our life, that third pair of eyes that’s just watching us in motion. The gap between our intentions and our impact gets wide. It was the best of circumstances, which were mostly not every day but mostly everyday is a pressure cooker.

It’s ten hours of nonstop decision making, trade-off making, appointing people, dealing with people tasks, dealing with rivals, dealing with shareholders, and dealing with the media. If you haven’t got somebody intentionally watching you in that space to see if the intentions you have and the impact that you’re making match, there’s no way any of us, no matter how much self-awareness and self-regulation we develop can ever make a consistent set of accurate conclusions just based on our own third eye. If you haven’t got help with that, that’s dangerous. That’s like a pilot flying with the radar off.

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The Pursuit of Transformational Change: If you haven’t got help with your decisions, that’s dangerous. That’s like a pilot flying with the radar off.

There’s different amount of help and different kinds of help you need based on how big the organization is. I talked to a young guy who owned a company in Cambodia. He’s great in marketing and he was great in sales, but he doesn’t understand the production operations efficiency and trying to decide whether to go with somebody to buy part of his company or to go out to get a consultant for advice. What do you tell somebody like that? What’s the next step to get better?

That’s a major strategic decision making. I’d want to know first of all, what is his strategy for the organization? What’s the competitive set? How was he planning to differentiate himself? If they’re planning to compete on service or on innovation or on some other mechanism where you can outsource production, or you can have somebody else make your product for you and your margins can tolerate it, that’s one thing. If you’re planning to separate yourself from your competitors, the question I ask all the time is, “Why should people pick you over somebody else?” Too often, you get the mission statement, you get the vision statement, you get the product quota, you get some strategic counterfeit, but until they can answer what are the capabilities that you’ve chosen to invest in, that if you put a dollar, you can get your pile on the door? In your case, that type of planning to compete on cost and price, he can’t afford to outsource that part of his organization. The price is not what’s the easiest or what’s the best thing for this company based on what I know, it’s what’s based on its competitive requirements and how you believe you could win in the marketplace and how you believe the people you’re going to serve, the consumers or the customers you want to reach wants to consume what you offer and why they would choose you over somebody else doing what you do. If you have the data and the insights and the experience to know what that is about your organization, you’re going to be flying blind.

My first question for any leader that is looking to influence the organization is what’s their strategy? Any good socio-technical systems thinking starts with, “Who are you trying to be? What is your identity?” Too often, entrepreneurs especially think that’s for companies. For us little guys, we’re trying to make our way up. My advice to most entrepreneurs is that it’s especially important for you to start tracking your field and get your swim lanes defined, because otherwise every yes you get out is the strategy. Costco called, that’s strategy. Walmart called, that’s the strategy. You’re chasing whatever revenues you can get through the door, the lights on, that’s not sustainable. Those leaders confuse growth and scale.

Let’s say they don’t have a business education. Is there a start for to learn about how to even develop their planning and strategizing?

You can spend a week at HBR’s website. They have all kinds of great information about strategy. They have great strategy planning tools. Just a simple Google Search can get you on with a ton of very basic insights and tools on how you begin to shape any of your organization. There’s a whole bunch of great pieces we use on strategy for entrepreneurs. How do you shape identity for a start-up? How the important fundamentals of strategy shaping apply to startups that they do to mid-caps or more mature companies? There’s podcasts. There are courses you can go take. There are also great advisors out there. You have to be able to afford them, and there are plenty of advisors out there who are affordable. You can afford to engage them for a few months to invest in; getting a good. If you can’t do it yourself, you did MRI.

Did you ever walk into a cardiologist and say, “I’m having chest pains right now,” and the cardiologist say, “That’s your upper ventricle, you can sit there and let’s operate on it right now.” You can say, “Don’t you want to look?” “No, I’ve seen it before.” You should run petrified from the room. You shouldn’t be operating on your organization unless you have an MRI, and it needs a good, robust diagnostician to do that. You have to pay a fortune for it. Your colleague in Cambodia ought to be thinking about somebody should look at this from a marketplace perspective, from a scientific perspective and say “What’s the potential? Where can it grow? What does the marketplace want from it?” If you own it, you’re biased. You’re already predisposed to believe that. You should believe in your baby that much, but you also should know that somebody can shoot babies out of the way and you should know who it is and why.

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Rising to Power: The Journey of Exceptional Executives

When you’re so in it, you don’t see everything, because you only know from your perspective. It’s important to get an outside perspective. You’ve written so many books. You’ve got these unbelievable bestselling books. Is your most recent one Rising to Power? How do you find time to write so many books?

I’m actually a writer, not an author. Writing is how I learn. The great questions you’re asking right now, when I see my clients not asking them the way they should, I go ask them on their behalf. The intractable, persistent, unresolved, and complex challenges that don’t seem to make any sense. When I feel like I’m happy no one asked me this question. I don’t have enough point of view, and a Google Search isn’t going to cut it or my friends at HBR aren’t going to help. I want to go deep. I’m going to go find out, “What the heck?” For me, writing is how I learn. It’s the research part of it and looking at patterns and trying to detect previously undetected patterns. For me that’s the itch I scratch and say, “Now I can go back to offer some incredible thoughts if and when the leaders would ask them.” For me, that’s the reason I do it, is to learn. I’m an introvert but my personality never gives it away. We all know that my people points run out pretty quick. Retreating into my own thought leadership, retreating into, “How would I say this? How would I articulate?” is one of the reasons I started enjoying writing for Forbes and HBR, which was a chance to go away and just collect my thoughts and think.

I’ve had quite a few contributors at Forbes and different individuals on my show that have written books on similar topics, but you have such a variety of unbelievable amount of knowledge and I thought a lot of people would be glad to find out more about this because you have some great content. Can you share how people can reach you and get your books?

They can come to our website at We got a lot of research. We’ve got a quarterly magazine you can get a subscription. We have a free eBook called Leading Transformation in Organizations, it’s our playbook. If they go to, they can get the free eBook there. We do research a lot. We did 25 amazing individual leaders like Dan Pink, Dorie Clark and a bunch of great CEOs and great companies. 25 phenomenal thinkers on the topic of leading influences so they can create their own personal virtual summit watching those. There’s lots of great resource there. They can download Rising to Power there, so it’s a great treasure trove of stuff to come play in. You can also find me on LinkedIn and Twitter @RonCarucci.

Thank you so much for being on the show.


You are welcome.


A More Beautiful Question with Warren Berger

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A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas

I am here with Warren Berger who believes questions are more important than answers. He’s the author of the international bestselling book, A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. He’s the Founder of the popular website, He also writes for Fast Company, Harvard Business Review, The New York Times, and Wired Magazine. Warren has spoken at top level conferences such as TED and has been featured on The Today Show, CNN and National Public Radio. He’s an outspoken advocate for bringing more questioning into our schools and occasionally visits leading companies to talk about the importance of asking better questions and business. It’s so nice to have you here, Warren.

Thanks for having me.

Everything you do is right up my alley because you’re about asking questions and the importance of it. I’m very fascinated by some of the covers of your books, especially the one with the guy’s face.

The advertising book. I’ve written about advertising and I’ve written about design thinking, which is related to design but it’s more about innovation. Finally, it gravitated toward questioning, mostly as a spin-off of my writing about innovation.

You find all these different topics and then you’d go, “What’s so fascinating?” I like asking questions and then you go backwards a little bit.

For the first time, I’m going to stay with a subject for more than one book. I am going to do a second book on questioning because the first book was well-received and I enjoyed the subject. I felt like there were a lot more directions I could take it in. I’m doing another book on staying with the subject of questioning.

It’s important because you’ve been talking about Silicon Valley and if you’ve asked the right question, that makes a billion dollars.

With the first book, I had a lot of focus on innovation. That became almost the basis of that book to say questioning is very much connected to innovation. It could be thought of as the starting point of innovation. You’re asking the right questions and it gets you on the road to innovation. That was a big focus of that book, but I found that there were other areas I could talk about with questioning that we’re as important, like what is the importance of questioning in terms of leadership. If you’re a leader, how important is it to be asking questions, and what questions should you be asking? I also looked a lot at a questioning in relationships in the book, like how does questioning help shape the way you interact with other people, and how can it help you to communicate better with other people, or maybe overcome difficult communication situations across the divide with people, and how can questioning help you do that. The book is like staying with questioning but taking it in some different directions.

You started looking at what stopped us from questioning. You say that kids ask 40,000 questions between the age of two and five. According to a Harvard researcher, at around age four, we start to get that why stage. I was on a bus one time and this little Hispanic girl kept saying, “Porque, Mama? Porque?” Which means, “Why?” She said that a thousand times.

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The Pursuit of Transformational Change: Kids go into school and they start to get a little older, that question-asking begins to tail off.

It crosses all language and culture, even though the word changes, the same thing is going on and it is curiosity that starts to bubble up at age two or three and then seems to hit its peak at ages four and five because now the kids are able to articulate their curiosity. It takes the form of just many, many questions usually directed at the parents or whoever else was around, but the parents get the brunt of it. They get a lot of those questions. What the research suggest is that as kids go into school and they start to get a little older, that question-asking begins to tail off. Some studies that have been done found that a lot of questions in kindergarten or first grade, but then less and less as kids go through school.

That’s an interesting development, particularly when you put it alongside the other thing I talk about in my book, which is that questioning is so important. It’s so important for innovation and for growth and for lifelong learning. You put these two things side by side, you see a decline in questioning as we get older, and you see that it’s so incredibly important to your career and to innovation and growth. It suggests that there’s a problem there. If this thing is so important, we don’t want to get out of the habit of doing it. We want to somehow maintain that habit and maybe even strengthen that habit. That’s one of the main points I try to make them.

It’s challenging for teachers because they’re maybe teaching to a test or they have curriculum guidelines they have to follow, if every kid goes off in a different direction. Some of it is in the classroom and it’s just natural. How do we keep that sense of curiosity and still keep the classroom?

We have to design or redesign some of the things we do in the classroom. I think some people are doing it already. If you look at the Montessori schools, you see various approaches that are a little different in terms of encouraging more inquiry and more collaboration among students. In general, our education process has to move a little bit in that direction. We have to get a little bit away from downloading information into students so that they can memorize it for a short amount of time and repeat it back on the test and then forget about it. That model is a little bit outdated. We now need to recognize that maybe the most important thing we’re going to impart to these students is not the facts themselves, the specific dates or facts related to certain things, but the ability. If we can give them the ability to find that information themselves, to even inquire about that information, develop their curiosity, develop their ability to wonder and then to try to search for answers to the things that they’re looking for or they’re interested in, that may be the most important thing that we can impart to kids as they’re going through school. We have to look at the way we teach and figure out how to strengthen those behaviors and that kind of thinking.

It’s important to ask the questions and as you said, “Questions are the new answers in Silicon Valley.” Steve Jobs said when they asked him what’s the single most important thing to his success at Apple was, and he said, “Throughout the years in business I’ve found something, which is I always asked why we’re doing things the way we’re doing them.” The Netflix Founder questioned why you had to pay late fees at Blockbuster, and that led to his company. You see great success stories. Is it something that you think that they are born with? Any of these big leaders, are any of them just naturally that way? Did they have a teacher maybe that promoted it?

It’s a combination of things. Some people are a little more inclined in that direction, but all of us can have that within us. It’s just a matter of whether we attempt to bring it out more and to strengthen it. There are people that have always been extremely curious and inquisitive their whole lives. A lot of the times that tendency sometimes when they’re young gets them into trouble, and some of the innovators and successful people, you find that maybe they didn’t always do that well in school. A lot of times they were considered outspoken. They were restless, they were challenging authority, including the authority of teachers. A lot of times they didn’t hit their stride until later on when they got out into the world and they started a company or started their own venture in some way and then all of that curiosity and questioning had paid off. Then it became a huge asset, whereas earlier it might have been seen in some ways as a trouble-making thing. Some people are more that way. It may have to do with their upbringing, it may have to do with just their personality. I do think all of us should find that side of us and try to bring it out.

We may be reluctant to do so because we’ve been conditioned to think that we should follow the straightened arrow and not necessarily question things, but just accept things as we’re told or as they are. All of us have the capability of moving in another direction, which is to be a little more of a questioner or an original thinker. The other thing about those people that made them successful is not only that they had a tendency to question the world around them, but once they raise the question, they would stay with it. They would pursue it, they’d work on it, and they wouldn’t give up very easily. That’s the second part of being a great innovator or change-maker, is you not only have to ask the questions, but then you have to be persistent about picking a question you’re going to work on and you’re going to devote yourself to and staying with it through all the trials and failures and things that are going to happen as you try to answer a difficult question. There’s two parts to it.

You brought up a questioning authority and made me think of the series about Einstein, Genius, which was awesome. Einstein’s always excited for things of curiosity. He said that if he had an hour to solve a problem and his life depended on it, he would spend the first 55 minutes making sure he was asking the right question. How do we know if we’re asking the right question?

You don’t always know if this is exactly the right question that’s going to lead to a breakthrough or lead to an innovation. You have to be asking lots of good questions and pursuing lots of good ones and some of them are probably going to lead to something special, and others may turn out to be just an interesting thing that you thought about and looked into for a while and maybe it led to something more and maybe it didn’t, but it’s still worth doing. It’s still worth pursuing. It’s still worth asking a lot of questions. What I’ve found in the cases of the innovations that came out of questions is a lot of times the person felt deeply about that question. There was something about it that stirred them. Maybe it was a problem that they were irritated by, “Why hasn’t someone come up with a better way to do x or do y?” It was something that meant a lot to them, because they were very annoyed by that problem and they and they wanted to see something better develop or come out of it. It’s a good question because it moves you. It stirs something in you, and it stirs a deep interest or passion. That’s probably one of the best measures of it. Then in the end, who knows if that question will ultimately lead to some type of breakthrough? The only way you’ll know that is to pursue it and see what happens, see what develops. In some cases, some of these questions may lead to something life changing, some of them may not. Some of them may lead to something smaller, where maybe you learn a few things and then you move on.

You’re obviously a curious person. When I was studying curiosity, I found there are so many things that hold people back but they fell into these four areas I was noticing, either fear-based or assumption- based, technology or environmental-based issues. You had a quote about Frank Lloyd Wright that you said, “An expert is someone who stopped thinking because he already knows.” To me, it’s assumptions. You think you know it all or you’re assuming you won’t like something. How do we stop that kind of thinking?

The only way you stop it is by being aware of it and by being aware of that trap and then challenging yourself to avoid the trap. A lot of times we fall into traps because we don’t know they’re there and we don’t see them. If we’re talking about a literal trap that an animal might step into or fall into, they fall into the trap because they don’t know it’s there. With any trap, it starts with awareness. Awareness that the trap is there and then thinking about some of the ways that you might avoid the trap. In case of the trap of expertise, just by being aware and making yourself aware that when you get fairly comfortable with your expertise or with your knowledge in a certain area, that there is a danger that goes with that always. The danger is that you will be too comfortable, and you will stop looking for new ideas, new ways of doing things, and you will assume that you know already, you will assume that the existing ways are the best ways, and the existing answers are the only answers, so you start to make those assumptions. Just knowing that that is a problem is the first step to overcoming it.

Then you come up with your own little strategies for dealing with that and for avoiding that trap. To me, the strategies are you have to make sure you always get input from outsiders, from people who maybe aren’t as steeped in that area as you are. In effect, you almost need the four-year old child of you, the naïve of you to go with your insider view. Sometimes that comes from talking to other people, sometimes that comes from trying to get yourself to think like an outsider. You can get yourself to do that. You can get yourself to say, “How would a child or a newcomer look at this particular situation? What if I put all my knowledge aside for a minute and I try to look at it in a fresh and naïve way?” You can do, anyone can do that kind of thing if you make the effort and you take the time to do it. That’s how we overcome those problems of assumptions. It can be as simple as asking, “What might I be assuming in a situation?” Simply asking yourself that question is the first step.

That just brings to mind the old, “What happens when you assume?” We may still make this joke and sometimes it goes back to that. You talked about the fears that we have in asking questions. I absolutely love that you cited Carlin because he’s one of my favorite. George Carlin said, “Some people see things that are and ask why, some people dream of things that never were and ask why not? Some people have to go to work and I have time for all that.”

TTL 182 | The Pursuit of Transformational Change
The Pursuit of Transformational Change: Some people ask why, some people wonder why not. Some people have to go to work and don’t have time for all that.

I used that line a lot when I go to companies and businesses. When I go to businesses, they’re very interested in questioning, but they have a mixed attitude towards it. The attitude is summed up in that quote from George Carlin, which is “Some people ask why, some people wonder why not. Some people have to go to work and don’t have time for all that.” It captures the idea that people may think it’s a good idea on a certain level to question more and to wonder and to be curious, but they also have to deal with deadlines and they have a job to do. In the real world, who has room for all of that luxury of wondering and questioning and doing all these things that take a lot of time? No one has time to do that because they have to just get their job done and meet the deadlines. That was one of the big issues around questioning, particularly in the business world where everyone is on a deadline, everyone is under pressure, that’s one of the challenges.

If you’re going to say, “We’d like a more curious questioning culture and we would like people within our organization to question more and to wonder and to use their imagination and their curiosity,” you can sell those things and it’s fine. It’s wonderful. But do they have time to do that? Do you give them the freedom and the space to think that way, or do you simply have them trying to keep their head above water every day and just hit the deadlines every day? It’s a conflict that businesses have to deal with. There’s no easy answer to it, but if you want innovation and you want creativity in your company, you have to come to terms with that conflict. If everyone is just trying to do the thing that’s right in front of them and trying to meet the today’s deadline or this week’s deadline, you’re not going to get a lot of creativity and you’re not going to get a lot of innovation. You’ll get efficiency, you will get efficiency, but you won’t get those other things.

You just brought to mind about how to know what to ask and how to know if you’re too close. If you’re in the company, sometimes you can’t see things because you’re in the midst of it all. It reminds me of a Neil deGrasse Tyson’s book, Death by Black Hole, which I’ve listened to a lot on audio and I love this book. He talks about how if you look at a painting, you see certain things. As you get closer, you see the paint strokes and the different things. You never know how close you need to get to something to see what you want to see. It’s a fascinating thing to know when to ask the questions and which questions to ask and if certain questions are not enough, you say why questions maybe aren’t enough. What happens if you don’t get the answer from why?

I’ve found that it’s three different types of questions. There are many, many types of questions but I focused in on three different types of open-ended questions that I found had an interesting relationship to innovation. That is why questions, and then what if questions, and then how questions. It’s interesting to look at those three types of questions and think about the differences between them. Each type of question is doing something entirely different. If you’re trying to solve a problem, you would use each question in a different way. I found even that you tend to use each question at a different stage of the problem-solving process. If you’re asking why, you’re trying to understand something. You’re trying to figure out why is this a problem. Why did it happen in the first place? Why is it so difficult to solve? You’re trying to get your arms around it. You’re trying to understand the problem, but that doesn’t lead to a solution. That’s just the first step. If you’re only asking why questions, you won’t move forward on actually changing. All you’ll do is you’ll get an understanding of the problem, but you won’t move ahead on actually changing it. To begin to change the problem, then you have to ask what if, and what if is about imagining other possibilities. It’s imagining what if things were different from the way they are now. That’s what you begin to activate your imagination, and you begin to come up with ideas and you begin to think about alternate ways of approaching this problem.

Even that is not enough to get you to a change or solution, because when you’re asking what if, you still are just speculating. You’re imagining and you’re throwing out possibilities and you’re speculating, ultimately you have to get to doing something, and how questions are very important for when you’re actually trying to get something done. Of those three types of questions, why, what if, and how, I would say how are the most practical questions. Once you start asking how you’re asking, how can I take the first step, how much would this cost to try to do this, or how many people would I need to help me, you start getting into practical stuff of taking action and doing something. I found innovators would cycle through that process. They would start out with a lot of why questions, and then they would start to use their imagination and then eventually they ultimately had to get to how are we going to do this, and that’s usually the hardest part.

You’re a longtime journalist with the New York Times, Wire, GQ. You obviously are a heavy questioner and have a great curiosity. I know so many people would want to know how to find out more about you. Can you share how they can find you and your books?

The easiest way to find out more is through the website I have a lot of stuff on there about a lot of research on questioning, a lot of articles, a lot of posts, a lot of stuff about me and about the book. It’s just a place where you can wander around and learn a lot about questioning. You can take a quiz to see what kind of a questioner you are. There are lots of fun stuff on there. There’s a list of songs that all have questions for the title and if anyone has another song to add to our list up, please let us know. We now have a very large list of question songs. It’s just all kinds of fun stuff related to questioning. There’s information there about how to do questioning exercises if you want to get better at questioning. If you’re a teacher and you want to get kids in your class working on asking questions in a better way, there are all kinds of stuff like that on there.

I hope they take some time to check out your site. I hope they also look at Carlin’s Vuja De, the backward way of writing Déjà vu, which means beginner’s mind. We all could use that in how we look at things.

That goes back to what we were talking about earlier with getting yourself to not be too comfortable and not assume too much. Vuja De is about going somewhere or doing something that you’ve done a million times before but try to see it as if you’re seeing it for the first time. If we can do that in our jobs or even in our lives, it opens up a new way of thinking. It opens up new possibilities.

Thank you so much for being on the show. This has been so much fun.

Absolutely. It was fun talking to you.

Thank you so much to Ron Carucci and Warren Berger. They were great guests. If you missed any of our past episodes, please go to and you can catch all episodes there.


About Ron Carucci

TTL 182 | The Pursuit of Transformational ChangeRon Carucci is Managing Partner of Navalent and is a seasoned consultant with more than 25 years of experience working with CEOs and senior executives of organizations ranging from Fortune 50s to start-ups in pursuit of transformational change. His consulting has taken him to more than 20 different countries on four continents. He has consulted to some of the world’s most influential CEOs and executives on issues ranging from strategy to organization to leadership. He has worked extensively in the health sciences, biotech, and healthcare provider sectors and in the technology, consumer products, and retail food and beverage industries. He has led work on several large-scale merger integrations and subsequent culture change initiatives and enterprise-level global organizational redesigns.


 About Warren Berger

TTL 182 | The Pursuit of Transformational ChangeWarren Berger believes questions are more important than answers. He is the author of the international bestselling book A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. He is the founder of the popular website And he also writes for Fast Company, Harvard Business Review, The New York Times, and Wired magazine. Warren has spoken at top global conferences (such as “TED”) and has been featured on the Today Show, CNN, and National Public Radio. He is an outspoken advocate for bringing more questioning into our schools. And he occasionally visits leading companies (such as ours) to talk about the importance of asking better questions in business.


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