Thirty Minute Mentors Podcast Transcript: Liberty Mutual CEO Tim Sweeney

I recently interviewed Liberty Mutual CEO Tim Sweeney on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a fortune 100 CEO and the leader of a business that generated more than $52 billion in revenue last year. Tim Sweeney is the CEO of Liberty Mutual, one of America's largest and most successful insurance companies. Tim, thank you for joining us.

Tim: Well, thanks very much, Adam. Great to be here.

Adam: Great to have you on. You grew up in Lowell, Massachusetts, 30 miles outside of Boston, headquarters of Liberty Mutual, and 30 minutes away from Harvard, which is where you went to college and where you went to grad school. But in many ways, Lowell is a world apart from both. Can you take listeners back to your early days? What early experiences and lessons shaped your worldview and shaped the trajectory of your success?

Tim: Yeah, sure. You'll still detect a mild Boston accent, given that I didn't travel very far for college or for the majority of my adult career. Here at Liberty Mutual. And so I like to say that the world came to me. So Harvard's global university and people from all over the world came to my backyard. And Liberty Mutual now is a global company right in the backyard of where I grew up. So, as you say, it's 30 miles, but it's a world away from where I grew up. And so I grew up the son of a pharmacist and a nurse. So I was always a healthy kid for obvious reasons, and we had a normal lower middle class upbringing. We had everything we needed, but nothing extra and nothing more. And I spent eight years in Catholic grammar school with the nuns and really learned values and right and wrong, both from my parents and from my early kind of religious education, if you will. And my parents used to always tell me that we had been given great gifts, and it's our responsibility to use those. And so if you were doing well in school, how are you going to deploy your energies to something bigger than yourself? So my mom particularly always reviewed my report card with me, and as long as I was doing my best and working my hardest, that was enough. But she always challenged me to make sure that I was doing that. And then, look, I would say we all have many innate traits in us, and I just always somehow was inspired to personally just because I get the best grades in classes and be the best math student. And so some of that I think was just innate. But I had wonderful teachers early on and just amazing parents. My grandparents used to live in Boston, so a 30 minute drive away and whether the spelling bee was coming up or the math tests were coming up, my mom would spend the 30 minutes in the car drilling me with math tables, multiplication tables, spelling words, et cetera, et cetera. And so just really supportive parents, a little bit of just my own innate desire to achieve and then really supportive education. I then went on to public high school. I'm a graduate of Lowell High School. I think I had a class of 600 at Lowell High School and kind of a big public high school where you really had to fend for yourself, and there were great teachers there, but you had to seek them out. If you just wanted to glide through, you could glide through. And so two things there. I learned to take the initiative and to make sure I was seeking out the best teachers. But number two, I was immediately, at a very early age, exposed to diversity of people from all different walks of life, went to Lowell High School, immigrants, people of different demographic backgrounds and ethnicities, etc. I think my hometown of Lowell now is. Majority nonwhite, and so I never really noticed that that was different. It was just normal to me. But as I look back on it, I realize that growing up in such a diverse environment and going to a high school that was so diverse really normalized that for me, and made working with and collaborating with people of all backgrounds just normal and business as usual to me, which in hindsight is a gift.

Adam: As you reflect on the lessons that you learned, as you reflect on what helped you become such a successful leader, talking about diversity, why do you believe diversity is so important, and how can leaders build truly diverse and truly inclusive organizations?

Tim: I live the benefit and value of diversity every single day and my role as CEO. If you were to look at my leadership team of the company. So I'm 30 miles up the road from Liberty Mutual's global headquarters. We do business in 29 countries, so we are a global business. I have a leadership team of ten people. My leadership team were born in five different countries. They are more than half female, and they are roughly 50% white and 50% nonwhite. And we have the most amazing, remarkable debates and discussions. Folks come at things from all different perspectives and backgrounds and life experiences, and you just have this richness of discussion and debate. And then, you know, we've created a team culture where after the debate and once the decision is made, we lock arms and move forward together. But the diversity itself, the fact that I have folks from five different countries sitting around my table every time we have a leadership meeting, just unleashes incredible creativity and innovation and different perspectives that improve the richness of the ultimate decision and thus the direction and success of the company. And so no one needs to convince me of the business benefit of value, of diversity or DEI. I live it every single day, and I also benefit from a diverse organization where we have been deeply committed for about 15 years, long before it became in vogue to have DEI programs and DEI leaders. We've been at it for quite some time, and we have ERGs for all sorts of different groups. I think we have eight ERGs now. We've got a pride erg and an erg for women and Asian Americans and Latinx and our black colleagues and our veteran colleagues, and the list goes on. We've got one called Abel, which is for folks with invisible and visible disabilities and their caregivers. And so I try to attend as many of those employee resource group meetings as I can, because I learn they make me a better person. They make me a better leader just by hearing storytelling and the challenges and microaggressions that people feel. And it helps me to create an environment where all are welcome and all can be included. We call our veterans employee resource group valor. I was just at a valor event yesterday, and we had a couple of veterans that are now in wheelchairs talking about all that they have overcome and their resilience and how they stay positive given all the challenges and trauma and tragedy that they've been through. And it puts in perspective, you know, the small things that I might get annoyed about any given day and it just makes you a better person. I've gone to a women's group, ERG, and learned about the challenges as moms go on maternity leave and have babies, and then how difficult it is to then come back into the work environment and leave those beautiful babies at home. And just hearing the challenges, the emotion, the mixed feelings about it all enriches the decisions that I will make and our benefits programs and how we think about parental leave, et cetera, et cetera. And so it just creates a richness of perspective, enhances your empathy, and ultimately leads to making better decisions. Because ultimately, we want to be financially successful so that we can ultimately keep our promises to our customers but you don't do that without being a best place to work, and we want to be the most trusted brand, a best place to work and financially successful so that we can fulfill our obligations to our customers.

Adam: Not only did you make a great case as to why diversity is essential for anyone leading a business, leading any kind of organization, but you shared some great tips on steps leaders should take to get there. Being personally invested. Showing up. There's no substitute for being there. There's no substitute for being present. Attending the employee resource group meetings. Making it a priority for you as a leader and prioritizing it not only with your dollars, but with your time.

Tim: I've long said nothing signals a leader's priorities better than how they spend their time. So it's not the words that they say, it's how they choose to spend their time. And where they choose to show up is really the indicator of what's important to them and by extension, what's important to the organization.

Adam: What do you believe are the key characteristics of a great leader, and what can anyone do to become a better leader?

Tim: First and foremost, and everyone in my organization knows this. Integrity. Full stop. You have to have integrity and be truth-telling because people will sense when you're not being straightforward. And so first and foremost, a sense of integrity and always doing what is right. And I like to say to my organization, if achieving our business and financial results is at odds with doing what's right, then we will miss our financial and business results because it means our plan is wrong if we have to cut corners to achieve it. Number one, number two, and the one that I think is most lacking sometimes as you go out and about Corporate America. Our global corporate world is courage. I always distinguish courage as the thing that is the difference between a manager and a leader. A lot of folks are good managers. They can make sure that things run on schedule. They can make sure that tasks get done. They can hire and fire as needed. But to really lead and to have people follow you and trust you, you have to have the courage to take the hill. You have to have the courage to make decisions in a complex world where you don't have all of the information you need at the time that you need to make decisions. And I've seen many managers, I guess, get paralyzed and not able to make those difficult decisions. And so you have to have the courage of your convictions. You have to know that if 70% of your decisions are right and 30% are wrong, that's very, very good. You're going to make the wrong decision. Sometimes, once you know it's the wrong decision, you need to admit it, correct it and learn from it, and then move forward. So courage would be number two. I think particularly in this world where there's so much over communication and social media and bombardment of information, digital and otherwise, coming at people. Clear, concise, repetitive communication is really important for leaders. So my mantra at Liberty Mutual is integrity first and then profit and then growth in that order. And we have another mantra which is win with purpose together, where we have clearly defined what winning means. We always remind people of what our purpose is, because purpose is what gets people out of bed in the morning. And we exist to help people embrace today and confidently pursue tomorrow. So people wouldn't buy homes, they wouldn't drive cars, they wouldn't start small businesses, they wouldn't build green energy plants and sustainability without insurance, without the products and services that we offer to help them manage the risk of those endeavors. And so we define what winning is from a commercial perspective. But we always talk about the purpose of the organization and then finally together win with purpose together because collaboration and alignment of a team. And I've got 50,000 people in 29 countries speaking multiple languages around the world. And how do you create the alignment to make sure that we charge that hill together? And that has to do with simple, clear, consistent communication in a way that is relevant and resounds with everyone. And so creating that sense of purpose, creating that alignment and communicating it in a really clear and compelling way, so that all 50,000 of those employees can see a clear line of sight from what they do every day, to what the goals and purpose of the broader organization is. Because no one wants a job, they want to be part of something that is having positive impact on the world and on society. And so those are probably the bigger things that I think are the key ingredients to being a good leader and leading a large, complex organization. It's not about being the smartest person in the room. I have people on my team that are smarter than me. It's about being the best leader and creating followership by building trust in the room.

Adam: You mentioned that you have an organization that consists of 50,000 people. That's a staggering number for many leaders out there. What do you look for in the people who you hire, and what are your best tips on the topic of hiring?

Tim: First thing I look for is cultural fit. Far and away the most important thing. Regardless of the accomplishments and experiences and intelligence of whoever's sitting across the desk from me, first in my mind is, will they fit here? Will they be culture carriers? Will they do things in a collaborative manner? Will they treat their peers, their employees, their managers, our customers with dignity and respect and decency? Will they make sure that integrity comes before financial results? And so that's at my company. That's the depth of the culture at my company. Other companies clearly have different cultures, but those are the things that are very important to us. We put people first. We keep things simple. We make things better. I'm kind of digging off the values of our company and making sure that folks are going to come in and be successful and drive the business forward in the right way that is consistent with our culture and values is number one. Number two, there was a general manager of the Boston Celtics years ago called Red Auerbach and smoking his cigar of course, he used to get up in front of the sports press every year before the NBA draft, and they would say to him, are you going to draft a guard or a center or a forward? And he every year would say, I'm going to draft the best available athlete. And so I've long had that in my head as I'm thinking about hiring decisions. There are some highly technical jobs that you need a narrow set of skills for. So that's a little bit different. But typically speaking I'm looking for the best available athlete. I'm looking for well-roundedness, especially in this day and age as the world is changing so quickly, the demands and pressures and risks in the world are changing so quickly. Technology is changing so quickly. It's really difficult or probably short sighted, to hire people that are just right at this moment because this moment is going to change. And so that notion of best available athlete, someone that obviously has the skills, cultural fit and the kind of work ethic and intelligence to do the job, of course, but someone that's got that versatility, that well-roundedness, that adaptability, that ability to collaborate and interact with others and create followership and create networks and drive results without full control. So surely you will drive results in a company by leading and instructing and holding accountable your team. But in today's large, complex corporation, you really need to get things done through influence too. And so that well-roundedness is really important.

Adam: Tim, you brought up a lot there that I'd love to dive into, starting off with the importance of hiring for cultural fit. When you lead an organization of 50,000 people as the CEO of the organization, you have limited influence over who each of those 50,000 people are and how each of those 50,000 people show up every single day. You're only one person, but what you can do is you can prioritize bringing in people who reflect your values and who are representative of the kind of culture that you want to build at your organization. And by prioritizing people who are going to be the right ambassadors for your culture, that's how you do it.

Tim: Oh, for sure. And look, I'm a big believer in tone at the top and cascading, tone at the top is really important and I communicate a lot to the organization through streaming videos and town halls. And I was just in Asia doing town halls for thousands of our employees over in Singapore and then Australia. And so, again, clear, consistent messaging, but not just what I say, but what I do and where I spend my time sets the tone at the top for what we will tolerate, what we won't tolerate, what we expect of our people. And then I make sure that everyone on my team, our culture carriers and fit the culture of the organization. Because values beget values, talent begets talent, and people look up to the senior levels in the organization and see how we conduct ourselves, how we behave, what we say if our actions meet, our words and what's important to us. And then over time, you create reward systems and promotional systems where only people that fit the mold, not just because you delivered good results in the wrong way, but because you did it in the right way, and ultimately the people that are fitting the desired culture and values of the company are the ones that emerge and rise up in the organization. And then you need, particularly when you're a values driven company like Liberty Mutual, you need a strong compliance function. And when lower in the organization, you have folks that are violating integrity or violating our values or managing people in the wrong way. You have to take action because you ultimately you get what you tolerate. And so this is the kind of the downside of almost cultural enforcement. But when people don't do things the right way, I want people do violate our code of conduct. They have to not be with the company anymore. And so tone at the top, cascading by making sure everyone at my table and then everyone at their tables lives our values and is a culture carrier enforcement at the bottom in terms of folks that don't do the right thing and a lot of communication in simple ways, and making sure that our leadership actions match our words and magical things happen because that culture that you create is what helps people make decisions when their manager isn't around. So you may not know the answer. You may not be able to talk to your boss or your manager or your CEO, but the culture gets baked in and helps instruct people as to what the right decision is. So it literally is the secret sauce of people making decisions when they have to do it on their own, without direction or guidance.

Adam: Something else you brought up a couple of times the importance of creating followership, which you linked to being able to build trust. How can leaders build trust?

Tim: I think trust is hard earned and easily lost. And I think authenticity and vulnerability, those are buzzwords these days, but I think they're really important. The notion of an all-knowing CEO was always a myth, but now at least we can talk out loud about it being a myth. I do not have all the answers, I will admit. When I don't have the answers, I will lean on my team. If anyone on my team doesn't know more about their part of the business than I do, then I have the wrong team. And so I think a notion of just being myself, being able to say, I don't know, being able to admit mistakes, being vulnerable in my interactions with folks throughout the organization, spending a lot of time one on one with folks, doing coffees and other chats with more junior people in the organization. Being humble, not thinking you're better than anyone in the organization just because of the role that you're privileged to play, and ultimately doing what you say you're going to do, and doing it with a sense of optimism because no one wants to follow a cynic or a pessimist. People want to follow and trust in someone who's optimistic and tries to expand the opportunity set for your people and for your company. I view my role now as giving people the tools and challenging them to achieve more than they ever thought that they could accomplish. And my joy and my job now comes not from any accomplishments of mine. I've had plenty of accomplishments over the course of my career, but my joy comes from the accomplishments of others that I've seen come up through this organization. And so mentoring, personal relationships one on one, not just the quantity of time that you spend with people, but the quality of the time, make sure you're paying attention, that you're focused, that you're not dabbling on your phone or otherwise distracted. Give people your undivided attention. Tell them the truth. Create a track record of integrity and honesty. Create a track record of success and progress and admitting of mistakes. And once you've conquered several hills in that manner, you've created trust in your organization to charge the next hill with you.

Adam: You ticked off so many of the most important characteristics essential to successful leadership authenticity, vulnerability, humility. The most successful leaders deeply care about the people who they're leading. It's not about you as a leader. It's about the people who you have the opportunity to lead. We spoke earlier about visibility, showing up, being present, being there. There's a difference between showing up and being on your phone and being distracted and checking a box and showing up and being committed, listening very different and being on the other side of the table. You know the difference.

Tim: The humility thing is really, really important because a lot of the theme of what we're talking about is how you become a CEO or how you have a successful career in business or other types of organizations. And the humility part is really important because I can tell you all the tactics and all the smart things and all of the great things about me that might have helped me get ahead here and there. But the reality is, a fair amount of it is luck and serendipity. There are several people at Liberty Mutual that could be the CEO. I just am fortunate enough to have been offered the role and been ready when the role was available. And last summer I talked to 2 or 300 of our summer interns in a kind of town hall type session, and one of them raised their hand and said, what advice would you give to we college seniors that want to be CEOs someday? And I said my first advice would be don't want to be a CEO, don't aspire to be a CEO. Because I'm blessed and lucky to be the CEO of a fortune 100 company. There were only a hundred of us to state the obvious, and there's a fair amount of luck and serendipity and people helping you along the way. And so I'm proud of my career and the role that I play. I'm fortunate. I don't feel like I deserve it. I've earned it, but it doesn't make me any better than anyone else. It just means I have certain skills that are being leveraged. But I've been with Liberty Mutual 31 years. I love the company and I would have been very, very happy with my career if I retired 1 or 2 jobs ago. I did not need the CEO, and I think those end up being the best CEOs, the ones that didn't strive for it and frankly, the ones that enjoy the journey. Because that's the other thing I say to those younger folks is you don't want to be singularly focused on your career are singularly focused on this is my career accomplishment to the exclusion of other things in your life, friends and family, and having fun. You know, I turned 60 next month. Life goes fast, and people that kind of somehow implicitly think in their head that once they achieve their goals, they will then be happy and they will then have enjoyment. It's just not how it works. So the biggest advice I can give to people is enjoy the journey. Work hard, be ready for opportunities when they come, but there's luck involved and you need to be comfortable falling short of your goal. As long as you've had a good journey and good experience, and you've worked with great people and you've accomplished a lot. And I think back to well-rounded people. People need to enjoy their lives and not over index on just career aspirations.

Adam: I really love that. What were the skills that helped you get to where you are today, and what skills do you believe are essential for anyone to develop to get to where they want to be?

Tim: Yeah, like I said, I'm not going to be the smartest guy at the company. I'd like to think I'm the best leader or among the best leaders at the company. As I think about what has helped me to advance within such a large, complex company, it is making sure I picked a company with the right culture so that the way I approach things is the way that can be successful at this company. And I could have worked at other companies where the culture is different, the expectations are different, and perhaps I wouldn't have been as successful. So making sure you're fitting in the right company and making sure that you're loving what you do every day, you have to enjoy it if you're going to be great at it. If you're not having fun, you have to do something different. I would say relationship-building skills and engagement and collaboration and creating a network. So people always ask me, who was your mentor? I've never really had a mentor. I view mentorship as a buffet table. I've had several, many mentors along the way where I've learned this from this person and that from that person, and then you stitch it into a mosaic that fits you and your style and your personality and who you are. And so I think creating a network and establishing relationships both inside and outside the company is really important. One thing that sometimes I like about myself and sometimes it annoys me about myself, is restlessness. I'm always restless. I never rest on success for very long. Do I celebrate it? Yes. Do I make sure my teams feel appreciated and celebrated? Absolutely. I get nervous when I feel like everything's perfect or everything's good. It makes me then immediately start to worry about what could go wrong. Where could we be better? There's no way we're perfect at everything. And so the reason I say I like and I dislike it is I like it because I think it fuels success for any organization or part of an organization that I lead. I dislike it because I don't allow myself to enjoy success or progress for very long before I'm starting to think about what else could be better, right? And so courage. I mentioned courage already, but courage to take chances, to admit mistakes, to learn from mistakes. Those are probably the big ones. Hard work and commitment and dedication and loyalty to your boss. Having your boss or the team that you report up into, having their success or that person's success be more important than your own success, ultimately, is the most important thing to your own success. People think you have your own agenda, or you're working for your own success, and not for the teams or for your leaders success. That can be a bit of a derailer you really want to be working in service of something bigger than just yourself.

Adam: In 2024, fortune named Liberty one of America's most innovative employers. In your experience, what are the keys to fostering a culture of innovation?

Tim: It's hard. It's challenging. You get to be such a large organization like we are, and hierarchy sets in and conservative mindset sets in because we are a large organization. And so tone of the top matters again. So I have personally invested my personal time not just as CEO, but in prior senior executive roles at the company, in visiting our innovation lab and making sure that our innovation was funded, and making sure that we celebrated failures and learnings from those failures, because you're not going to push the envelope hard enough to innovate and to come up with new ideas, to try new things. If you penalize failures, you know they need to be well thought out failures. They need to be things that weren't reckless or outsized before they were ready for prime time, but not penalizing manageable failures. Celebrating them, talking about what you can learn kind of fail forward as a mindset, if you will. Providing the funding, getting things to market as quickly as you can so you can start to see successes. Because success breeds success. And so you get momentum by having innovative ideas, by getting them into the marketplace. And two out of three of them are probably going to fail. But that one that succeeds. It will then get the fire in the belly of the folks to come up with the next one. Making sure that we focus on the customer. So some people will just want to innovate for innovation sake and chase the shiny objects. But it really has to start with your customers. And what are the pain points of your customers, and what are the unmet needs of your customers. And so you have to start there to really have relevant and commercializable and scalable successes in whatever business you're in. It has to be meeting an unmet need of a customer. It has to be addressing pain point of a customer. And if it's not doing either of those two things, you have to wonder why you're doing it. Next is creating a use case and literally writing a narrative as to how this innovation, or how this new product or service will roll out, will work, will make the customer ultimately better. And so not creating solutions in search of a problem, but really making sure that you focus quite a bit on use cases. Next is minimum viable product, which is pretty common terminology in the innovation space. Just getting the bare bones thing, proof of concept up, giving it a try, tweaking it, etc. Instead of consuming tons of resources and time driving toward the perfect innovative product. And so you really need pace, and you need to fail fast and move on to the next thing when something doesn't work. So, as I said earlier, culture is just as important as anything else. But you need to show visible leadership support. You need to fund innovation efforts. Even when you're not seeing an ROI, so to speak. You have to have an intuition that creating an innovative spirit and an innovation capability in your company is ultimately going to pay off. Now, ultimately, you need to see the ROI of the investment, but not trying to measure it in too short of a time because it takes time. Those are probably the biggest things.

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

Tim: So no substitute for hard work, hard work, commitment to whatever path you are choosing. Relationship building and truly, truly, I can't emphasize this enough. A belief in serendipity. A belief that opportunities come unexpectedly that you wouldn't have seen coming. And so I hate the question: what do you see yourself doing in five years? Or what do you see yourself doing in ten years? Because whatever you think is going to exist as an opportunity in 5 or 10 years is not going to exist, or is unlikely to exist or is going to have changed substantially. And so the notion of serendipity and believing in chance events, at one point in my career, our CEO, so two CEOs ago tapped on me to go run our distribution organization. I hadn't sold anything since my lemonade stand when I was 11 years old, and now I was running a major financial services distribution organization in the US and talking yourself into the deep end. And so back to Red Auerbach and the best available athlete. Your learning curve is the steepest when you're outside of your comfort zone. And so take chances with your career. Everyone has some level of imposter syndrome. Fake it till you make it kind of thing. And so don't seek to be perfectly comfortable in your next job or your next opportunity. Move horizontally as well as vertically. In organizations, it's where you will have your steepest learning curve when you are out of your element in uncomfortable situations. So that's probably the single biggest is get out of your comfort zone, and that's where your growth will be the most accelerated.

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

Tim: Great to be here, Adam. Thank you very much.


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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