I recently interviewed Charles Conn on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a leading technology entrepreneur and investor. Charles Conn was the founding CEO of Ticketmaster, CitySearch, a pioneering internet company whose portfolio included Match.com and Evite. Charles is also the author of the new book, The Imperfectionists: Strategic Mindsets for Uncertain Times. Charles, thank you for joining us.

Charles: It's really a pleasure to be here. Thanks for having me. 

Adam: The pleasure is mine. You grew up in Massachusetts, which is where you went to college and grad school before working in the world of management consulting, ultimately becoming a partner at McKinsey. Can you take listeners back to your early days? What experiences and lessons were most instrumental to shaping your worldview and to shaping the trajectory of your success?

Charles: Yeah, well good question. The memory that really popped into my mind was a third-grade memory, which is being asked to bring in a baby jar full of water from a local pond in Concord, Massachusetts, where I was a kid. So this is a pond not three miles away from Walden Pond that the role made famous. And we looked at a drop of that pond water in a microscope and saw all the creatures inside the local pond water. And that was one of those incredible awakening experiences for me. And in many ways to problem-solving. discovering these incredible worlds within worlds was one of those, yeah, transformational experiences for me. Good thing that I always think helped shape who I became is that my dad is an MIT engineer, and my mother is an artist. I think it's really healthy to have the interplay both of formal science and structure which engineering is representative of, and creativity in whimsy, which the humanities and arts are more redolent of. So I think that's been pretty fundamental for me.

Adam: What were the most important skills that you developed early on, as you were rising within your career, and what were the most important skills that you've utilized as you were leading people and leading teams throughout your career?

Charles: The most important skill for me all the way along has been problem-solving. My brother was an amazing athlete who played hockey for WIU. And I always wanted to be that. And what I ended up being good at was taking apart complicated problems, figuring out what the most important part of them was, and then providing good answers to the solution. So that capability has been the thing that's been the real backbone of my set of careers. As you pointed out at the beginning, I've done a lot of different things. That's the strand, the main strand of it. What I learned leading people, of course, is just how, and this was a rude awakening. Because as you say, I started at McKinsey. And in McKinsey, almost everyone you work with is a type A analytic. And you, therefore, assume that a particular way of solving problems is the only way to solve problems. And when I became an entrepreneur and started building companies, I discovered that there's a much richer set of capabilities out there in the world. There were people who work for me, who couldn't balance their checkbook, but who could do amazing artistic renditions of websites so or there were web architects who could create these most remarkable systems for supporting our technology, who couldn't look you in the eye and have a conversation with you. I discovered at that time in my career, how many different diverse skills it takes to build something enduring like a company. And it gave me respect for a broad set of ways of cracking problems, not just my analytic approach to it.

Adam: And it really plays into a few key themes that I think are critical to success as a leader and critical to success as an entrepreneur. First and foremost, self-awareness and understanding what makes you great, understanding what makes you unique. Recognizing that, to your point, what might make my brother great, what might make my brother unique, is something that I don't have isn't a defining characteristic for me. But what defines me is something that many, many, many other people don't have. And that's what makes me special. Recognizing that is a critical first step. And that allows you to understand who to surround yourself with, that allows you to understand how to build the right team around you.

Charles: Yeah, that sounds right. Part of that transition is moving from being the clever young person who's telling to being a little bit wiser, and instead shifting to asking. I wish I could say that was a transition I made early and easily.

Adam: A transition that you made early and it sounds pretty easy. Was this transition from McKinsey consultant to highly successful entrepreneur? How did you make that transition? Why did you make that transition? What advice can you share with listeners from what you learned from making that transition?

Charles: Well, I would say that was a really hard transition. And again, I think there was lots of coming up. And in that transition, that world of strategy consulting, played particularly well to that skill set, being clever and good at taking apart other people's problems, was valued very highly in that strategy consulting environment, what I got excited about, which is the internet was starting to happen in 1994. And I felt like I was missing something just as an advisor to other people, rather than being a principal or having my hands in it. And so I went to my partners in McKinsey, and I said, I gotta go will be part of building something. I thought that I knew about 90% of what you needed to know, to build a company and that I would have to learn this very difficult 10% that I didn't know. And as you could probably already imagine, I discovered very quickly that I knew about 10%, about what was important to working with other humans to build something, and that I had 90% to learn. And as I described earlier, recognizing that there's this incredible diversity of talent, and learning to respect and draw up on all those different contributions took me years and wasn't easy at all.

Adam: Recognizing the importance of surrounding yourself with the right people, an important early theme. What did you look for in the people who you hired? And what are your best tips on the topic of hiring?

Charles: So first of all, hiring is the first, second, and third job of building anything. And it's almost always the difference between doing really well and not doing well. And it's amazing to me that so many people in business, leave hiring two firms and other firms compensation and recruiting firms. The most important thing to my mind and hiring is to be very personally involved in it, not to let other people do the interviews. And then once you found someone who you think might be a nice fit for the job, to do reference checks, off-road meeting people that they didn't tell you to check references with, and not stopped doing reference checks until you know what the issues are. Because everyone has issues. And once you know what those issues are, you know how to work with that person. So it's not mostly about knocking people out. It's about knocking people in and knowing in advance people's strengths and weaknesses. That's something I think you should never devolve to other people. That's the lesson I learned.

Adam: I love that advice. It speaks to a broader theme that we're going to talk a lot about over the course of this conversation, which is the importance of understanding imperfection. No one is perfect. And oftentimes, is the imperfection and understanding of how to live in a world of imperfection that allows us to become successful, recognizing that no candidate is going to be perfect, recognizing that no candidate is going to have every single thing that you want. But understanding what does each person bring to the table? And what can I live with? What can't I live with? And if they bring something to the table? That is too problematic for me to live with. Okay, I'm not going to hire them. But by recognizing their strengths, recognizing their weaknesses you understand as a leader, this is how I can most effectively lead them.

Charles: Yeah, that's right. That sounds exactly right.

Adam: What do you believe are the key characteristics of an effective leader and what do you believe anyone could do to become a better leader?

Charles: I don't think there's one formula for being good at it. And I don't think any one company or any one nonprofit is a mirror to all leadership. That is I think part of leadership is contextual. But if we were to try and draw some lessons from good leadership, I think maybe the most important one, and it's one I learned from working with Yvonne Shannara. Patagonia is to set very high goals, so very audacious goals. And to constantly ask ourselves, can we do better? Not in a way that's mean-spirited, but in a way that leads you to constantly ask yourself, can you do better? And you step up. So that is probably the most important role for a leader, which is to lead by painting a vision of where you can go and making sure that vision is worthy and substantial enough. And then at least what I hoped for with myself, is you're as far away as you could be from being a micromanager that you really give people the freedom to operate within their space, working toward that common goal that you've established. And I think to do that, right, you have to be speaking to people a lot speaking with each other a lot. And that's the theme that we talked about a lot in the book, which is experimentation is critical to doing anything that's worth doing. And encouraging, working together to figure out what experiments are the ones that are going to lead your business or nonprofit forward. And making sure that you're capturing the lessons from both successes and failures.

Adam: Set high goals, set high standards, give people freedom, give people room to fail, and prioritize communication. Can you describe your own evolution as a leader? How did you grow into becoming the leader that you became CEO of this highly successful company? You lead, what is now Ticketmaster, you lead this conglomerate of major technology companies. What was your journey? And how did you get there?

Charles: Well, yeah, and I think my comments have probably painted some of that path, which is, I started by thinking that having the right answer was everything. And that if you had the right answer, people would naturally follow that and make it happen. And of course, what you realize pretty quickly is that doesn't work at all, that you actually need to cut, you know, you can set goals together big, big, audacious goals together. But the whole art of leading and building something together is not to say I know the answer, please do this. But to say, here's our goal. What are the ways we can achieve this together? And that's the journey that I went on from being well, it's sophomores, isn't it? It's the definition of wise fool. The sophomore, thinking that having smart answers is the whole way forward, when in fact, problem-solving together? Definitely, without knowing the answer is the only way to build something that's genuinely big.

Adam: Was there a particular experience that smacked you in the face and gave you no choice but to understand that?

Charles: Yeah, I was sitting in a hotel room. And I remember I was laying on the floor with my feet up on the bed. And I was talking to my dad. And I was just talking about what was happening at work. And I probably talked for 15 minutes, and he was just listening, and finally getting interrupted and he said, “Son, you're not very nice”. I thought, shit. I've never forgotten that. And then I realized that I was doing that thing that people do, which is I was running people down, because they weren't doing what I thought they should be doing. Instead of actually, working together with those folks so that we could accomplish something together. It was more of a judgment approach as opposed to a collaboration approach. And my dad's fairly sharp comment, I hope will be on a different route.

Adam: And it really speaks to the importance of listening, the importance of humility. The most successful leaders are open to listening to other voices and are interested in getting the perspectives of those who can help them become more successful help them become better leaders. In this case, it was your dad, who gave you the feedback that you needed. Feedback as in the words of Bill George, the former CEO of Medtronic, he told me on this podcast, feedback is the breakfast of champions whether you're getting it from your dad, your spouse, another loved one, a friend, a colleague, a coach, a mentor, embrace it, seek it, get it.

Charles: That sounds exactly right, you said another word that's really important, which is humility, or humbleness in another form. And when people first are put into leadership roles, they assume that there's this model of leading from the front. And there's an element of telling people what to do. That's when I worked in a supermarket as a kid, that was the model of the leaders telling other people what to do. And I think there was this assumption that showing any weakness would open up opportunities for people to get away with something. And of course, that's entirely the wrong way to think about things that people want to see vulnerability in their leaders. And they they want to know when we don't know the answer, especially when we don't know the answer. Because it makes them feel like they can be co authors of what the answer is. And ultimately, people only put their everything into something if they feel like they're part authors of it. And they have some autonomy in their work. And if folks believe those two things, and you set the goals correctly, together, they'll do anything.

Adam: So many of the themes that we've been talking about, speak to the importance of culture. Any tips for listeners out there on how to build a winning organizational culture?

Charles: Yeah, so you're all this stuff about how to run companies or run nonprofits. The thing that seems the most important to me, is to actually trust people all the way down through the organization. And I think if you can operate with a very simple, powerful set of goals, you have a company culture, you said it a minute ago, where the values are very clear, you really can trust people to do the right thing. And then the last part of it is to not punish people when they make good experiments that don't work. And I think that's the hardest thing is companies get bigger. They want to think that they can make decisions on high and just have people execute them. And they get afraid of making mistakes. So they punish people who take experiments that don't work. When you look at great companies, they celebrate people who take the initiative and do experiments, whether they work or not. As long as those experiments are ones that are relatively modest cost, and reversible experiments or decisions that are very costly that the firm decisions or that are irreversible, we can't travel back through the door. Those are decisions that should be taken very carefully and higher up the organization. But most decisions aren't like that. And big companies act as if all questions are life and death questions, and they're not. You gradually disempower everybody down below. And you wonder why they work with subtle resentment.

Adam: Do you have any advice for people working within organizations where that culture might not exist? Because the culture you're articulating, is a culture that I've heard articulated from the best leaders who have come on this podcast. When I ask leaders who have built the most innovative cultures, the most innovative companies, companies that have fueled incredibly innovative technologies, multibillion dollar businesses, businesses that are growing and incredible clips, how do you create winning organizational cultures? How do you create cultures that fuel innovation? The answers they give are very similar to the answer that you just gave. What happens if you're working at a company that doesn't have that culture? What do you do? Can you change that culture from the inside? Is it not fixable? If you're not a leader? Do you need to go and get a new job? What advice do you have?

Charles: The short answer is sometimes you gotta quit. But before I quit, what I would do is ask for the ball. In all businesses and nonprofits, people are always excited when they have clever young people working with them. And if those folks say, hey, give me the ball. I want to run with it. And you trust folks enough to let them run with the ball, then you can maybe begin to change culture. Because you can demonstrate that even or especially the closer you are to customers, and what's sometimes called the coalface, the closer you are to customers, maybe the better decisions you make around what experiments to do. So my advice is ask for the ball. And if they let you have the ball, show him what you can do. And if they don't let you have the ball go somewhere else. Life is just too short to work places where they won't let you. 

Adam: I love that advice. A lot of what we've talked about really touches on the themes that you've explored in your new book, The Imperfectionists: Strategic Mindsets for Uncertain Times.  focuses on strategic problem-solving in times of high uncertainty. Right now, leaders are certainly grappling with how to lead in times of high uncertainty. What is your roadmap for leaders on how to lead in times of crisis, uncertainty, and major change?

Charles: So let me first say that I think a lot of the models that many leaders were taught about how to do strategy or really outmoded. Most people in leadership positions today were taught strategy in a world that doesn't exist, they were taught strategy when industries had clear boundaries, and there were clear players, and you could assess those players' relative strengths. That model or set of models, is basically we understand the market, we understand the structure of competition, therefore, we understand the conduct of the players. And you set up strategy paying attention to that. Michel Porter's Five Forces is a classic of that way of thinking. And most people didn't stop and update that as the world today. So now we live in a world where we have artificial intelligence, automation, robotics, programmable biology, and faster and faster change. In this world, industry boundaries are much less clear that a competitor that topples you, if you're a leader in a particular space, is more likely to come from outside your existing competitor space from entirely left field than has ever been shared before. And we live in a world where there are super competitors, companies like Apple, or Amazon or Google, who compete in multiple industry segments, and are constantly entering new words. In that world, that bold market structure conduct way of thinking doesn't work at all. And what's happened is in both nonprofits and for profits, when people's strategic planning process, which is kind of an annual process starts to work, nobody knows what the hell to do. And so what it's led to is people freezing, becoming risk averse, and sitting on their hands, which paradoxically makes them even more vulnerable to disruption by others. And so, in that context, I think the right formula for developing strategy is the one that you and I were hinting at already, which is to become an experimentalist. And to learn about the game that's being played in the structure, and that's out there by actually making small moves that help you build knowledge that helps you build skills help you build assets. So if I can make that concrete, look at how Amazon entered consumer financial services, did it use its giant balance sheet to buy a bank or consumer finance company? No, it didn't. What did it do? It made an investment, a little FinTech company, it hired the team of a failed FinTech operator. It bought some IP from another player. And it started a couple of little tiny skunkworks initiatives inside Amazon. Almost all those steps look like they failed because they were shut down. But over time, Amazon was building an idea about how to compete and consumer financial services that was radically different from anybody else. From 2007 to 2018-2019. They did a set of very clever small moves that slowly positioned themselves to the point where Amazon pay is got a 24% payment share across the U.S. economy. That's really clever. And they didn't do that by having a strategic framework or by making a bet the farm acquisition. This is this idea of imperfections and experimentalism, that's core to the book.

Adam: And so much of it really comes down to read thinking the way that we think of the word failures. When you think of the word failure as something that is terminal. And that's it, you fail, you're done by by this framework doesn't work.

Charles: That's right. And I think, what are the elements of that? And you talked about them earlier, like humility is actually part of that, which is accepting that we don't know. And that the leader doesn't say, here's the answer. The leader says, here's where we need to go. Here's our goals. You guys figure it out. And the elements of that are fundamentally curiosity, which big organizations often squash, curious people ask questions. And that's annoying. Experimentalism. So instead of just accepting existing datasets that are out there, try and find a natural experiment. As I said, hire a team. From over here, the worst thing that happened is you can decide that that team isn't any good. Buy a piece of IP, do experiments. The third piece that seems really important to me, is to be honest enough to know that the people with the right ideas may not be inside your existing organization. Bill Joy, the founder of Sun Microsystems is famous for saying the smartest people are not in your room. And so how do you get them in your room? Well, Bill Joy did it by open source software. Right, he was one of the architects of Unix, when he was at Berkeley before he became part of Sun. That idea that we don't need to find the source of every bit of intelligence inside our existing organization frees you up to use, for example, crowdsourcing via platforms like Kaggle, or open sourcing way many software companies develop themselves to bringing ideas in from outside that may be a critical kernel that also requires humility, because it says, even if I'm IBM, I don't have all the ideas. Even if I'm Amazon, I don't have all the ideas. Those three elements are just critically important to developing this and perfectionist approach.

Adam: I love it. It speaks to a number of other themes that are critical to leadership that are critical to success in business critical to success in anything, collaboration, empowerment, the notion that you don't always have the best people on your team, recognizing that it's impossible to have an A in every single department on your team. It's great in theory, but on paper isn't really going to happen. So that intellectual honesty is essential to success.

Charles: Yeah, we call it epistemic humility, which is like deep in your theory of knowing, you accept that you can't know everything. And I think that extends to management. Obviously, as organizations get bigger and more complex, the idea that one person could actually be the conductor or architect is observed. One person can be an Inspire. One person can set an example one person can live certain virtues or values. And I think invention art in a place like Patagonia does that. But that person can't be the architect of everything.

Adam: I want to go back to a concept that we've talked about touched upon, it's been an underlying theme of this conversation. And that's failure. You've obviously enjoyed enormous success over the course of your career, enormous success in so many different areas. You were a partner at McKinsey, the founding CEO of this incredibly successful company, you're a highly successful investor didn't even mention the fact that you lead the organization that oversaw all the Rhodes scholars the list goes on and on, we could have spent the entire podcast just listing off all the things that you've done so successfully. What do you consider to be the most significant failure of your career? And what did you learn from it? 

Charles: There have been many. I think you have to be honest about that. There have been many failures in any one of those jobs that look so great from outside, I have made really significant mistakes. And I described already at the beginning of what became City Search, Ticketmaster, and Match.com. I was a fool. I was a smart fool. And fortunately, I had friends and colleagues around me who help piece together a leadership team that was effective enough for me to learn enough to actually grow into be the CEO. But that was pretty touch and go and I will tell you, we miss payroll on a couple of occasions through that period where we hadn't done enough to be worthy of being investable and barely got the money we needed to keep the company going. So there was plenty of failure and all of those jobs jobs. Even recently, I took a job after doing the roads job doing a turnaround of a venture capital company here in the U.K. And I was fired from that job. I thought I was doing the right things. But I didn't convince the board that I was doing the right things. And I get fired. So there are lots of these careers that look wonderful from the outside. There's lots of failure. And there's lots of going back to the drawing board and thinking, oh, I didn't see that coming. What can I learn from that?

Adam: And it really comes back to not treating failure as terminal. It really comes back to recognizing that failure serves as a learning opportunity serves as an experience that can allow you to become all that much more successful.

Charles: But it's hard to do, right? Because your ego gets caught up in it. And so when something doesn't go well, and we all have that inclination to put it under the rug, or to run from it, or to say that it isn't, so this epistemic humility idea, is one where you just let go of the idea that you could be perfect anyway. And recognize that all successful people stand on the shoulders of others. It's funny, because President Barack Obama was criticized heavily for saying you didn't do this, or you didn't create this, or you didn't make this. I think he said he didn't make this in his speech. But of course, he was right. All great and successful people rely on the all the pre existing conditions that are even allow us to create great companies or great nonprofits. And then all those leaders also rely on all the people around them. And it's such a mistake to do this ex post attribution to a single person, you made this, you didn't. Hopefully, you played an important role in inspiring it. And hopefully, you created the right environment for others, so that they could be their best.

Adam: Charles, that is a really important point. And it speaks to the importance of recognizing that no one gets there alone. We all need the help of others, to become the most successful version of ourselves. Mentorship is critical. Having many mentors, having people in your life, whether it's someone who has a constant presence, or whether it's someone who, through one interaction, can help change your perspective can help change the way you think of things. Yeah, just think about my dad, my dad has done quite well over the course of his career came from relatively humble means. But if you talk to him about it, first thing I'll tell you is he was the beneficiary of public education, went to public schools grew up in an environment where, without that, where would he be?

Charles: Right? And that's what it means, you didn't make this. And the so-called self-made man, or self-made woman is fantasy. And there's an unbelievably deep arrogance. And then every successful person, there's a bunch of stochastic good luck and a bunch of other people whose work made the conditions for that possible.

Adam: Charles, what can anyone listening to this conversation do to become more successful, personally and professionally?

Charles: Well, I think we've touched on most of the elements of that, which is, we talked about the personal characteristics of curiosity, seeing things from multiple perspectives, rather than just your perspective, being willing to experiment and accept failure that comes from experimentation, being willing to admit that you need to take some of your ideas from outside, these are all these elements, those are all things you can do practically to make your career work better. Then maybe the most important thing is the thing we've been talking about here, which is values-based, which is to have a kind of epistemic humility, to understand that we rely on others. And therefore, I think there's a logical corollary that we haven't exactly said yet, which is to be successful ourselves. We need to bring out the best and others because only all together, do we achieve great outcomes. To bring out the best in others, you have to do something that's really hard, which is every interaction you're in, you need to ask yourself, how can I be of service to the person that I'm in the interaction with? Not what can I get from this person? Or what can they do for me, but how can I be of service to them? And if our orientation is not of service. Other people will be of service to us to humans are just animals. There's this reciprocal behavior pattern that people evidence if you behave like that, they will behave like that to you. And then you will achieve great things together because you will have shown people the fundamental respect, that you believe there's value in them enough to be of service to them.

Adam: Charles, thank you for all the great advice, and thank you for being part of Thirty Minute Mentors. 

Charles: It's been a great pleasure. I really enjoyed being on.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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