Be Yourself: Interview with Damon Hart, Chief Legal Officer of Liberty Mutual

I recently went one on one with Damon Hart, Executive Vice President, Chief Legal Officer & Secretary for Liberty Mutual Insurance.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Damon: I spent the first 15 years of my career in Boston law firms as a generalist litigator where I had a variety of clients, including some insurance clients. In 2014, I joined Liberty Mutual to lead employment law. I enjoyed the experience and felt like coming to Liberty Mutual offered a broader value proposition in terms of the type of work, leadership, and quality of work vs. how many hours I was billing at a firm. I was promoted in 2016 to the general counsel leadership team – still leading employment law. After a few years,  I was pulled up to help lead the litigation group consisting of 86 legal professionals. Shortly after that role started, Covid hit. I was still leading the team and the process but was doing it all from my kitchen table or basement. In 2021, I was promoted to Deputy Chief Legal Officer and spent about 15 months shadowing the former CLO Jim Kelleher, really learning the nuts and the bolts of the role. It was a thoughtful way of doing a transition and I’m grateful that I had the opportunity to sit with Jim and learn from him. I feel like it set myself and the organization up for success. On January 1, 2022, I officially took on the Chief Legal Officer role and haven’t stopped running since! Reflecting back on my career, I feel fortunate that I haven’t experienced any major challenges or setbacks. I have, of course, experienced micro setbacks like losing a case or feeling like I could have done better at preparing for big meetings, but with all things that don’t go your way, there are lessons about what you can do better next time. Having a mindset of continuous improvement is so important. You don’t carry around those setbacks, but instead, you learn that it’s all about making you better.

Adam: In your experience, what are the defining qualities of an effective leader?

Damon: I’m a big sports fan, and I like to think that being an effective leader is very similar to being a professional athlete. On a squad, everyone plays a different position and has a different but complementary skill set. It’s important to know the value each player brings, to value the discipline and teamwork, and how to be your best when the pressure is on while motivating those around you. In my experience, the best leaders are transparent with their communication and empathetic to the needs of their employees. Empowering their employees and nurturing their growth allows them to implement effective policies and core values to inspire team alignment and momentum. Creating a sense of belonging for your team will serve as a catalyst for overall efficiency and productivity. Fostering a culture that nurtures diversity, equity, and inclusion allows people of all backgrounds to thrive. We are a global company, servicing a diverse customer base. Having a diverse and inclusive organization promotes innovative thinking, which yields stronger business results, and ultimately work that reflects and better impacts those who we serve.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

I personally love professional development. I’m always actively doing something formally or informally because as a leader, you can’t pretend to know everything. My advice for aspiring leaders is to be honest about your leadership skills and where you stand – whether through a formal assessment or conversations. All of the advice that feels like criticism isn’t wrong. Set out on a path that seeks to learn from the people that know things you need to know. Connect with them, ask questions, and see what you can contribute back to them. Stretch yourself to learn something new.

Adam: What is your best advice on building, leading, and managing teams?       

Damon: My leadership style is rooted in teamwork, draws the best from the past while also constantly evolving. My best advice on building, leading, and managing teams is to focus on creating an environment where people can be themselves and do their best work. Credibility and trust are essential. I am direct, but always empathetic with my teams - I don’t get caught up in hierarchy. I’m grateful to work with a team that is great with structure because I don’t always paint within the lines and they help keep me balanced. 

Adam: How can leaders build a more equitable workplace?

Damon: Fundamentally, legal departments should care about justice. In the end, a lot of DEI is about justice – so it’s marrying up the business imperative with the moral imperative. It’s good for business and frankly, it’s the right thing to do. As a values-based organization, Liberty Mutual exhibits and walks its values as a company every day. In a lot of ways, the legal department has been an innovator and leader in this space. Diversity is like any other business problem – we address it head-on, we partner with others to ideate and innovate. We are shining a light on underrepresented talent and bringing them along and we are committed to making Liberty Mutual a great workplace for legal professionals. 

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders? 

Damon: The world of entrepreneurship is not that great of a departure from that of executive and civic leadership. My three tips across the board are to be optimistic and adaptable, prioritize upskilling and growth, and engage with your team in a way that allows you to be empathetic. Whether an entrepreneur or a C-suite executive in a company, challenges and setbacks are inevitable. As we have seen following the onset of the global pandemic, the entire business world has transformed and the companies and business owners that have been able to weather the storm have been open to adapting their business models to cater to the needs of their employees. There has been a great shift from prioritizing customer needs only, to those of the workforce, especially following the Great Resignation. Being flexible and open to new benefits and work perks are necessary in order to stand out in the competition for talent.  Additionally, the most effective leaders can inspire and motivate their teams even in the most trying of times. Maintaining an authentic yet optimistic mindset is contagious and builds team morale when the going gets tough. The saying ‘lead by example’ couldn’t be more relevant to the point of constantly seeking growth opportunities as leaders. To my previous point, in the ever-changing world we live in, there are always new ways of working and technological advancements to indulge in. Keeping up with the latest business trends and upskilling can help you to be a more effective leader, and encourage your team to strive for more as well. Finally, having a people-first mentality is truly paramount. The workforce is as diverse as ever, with a combination of multiple generations, with a variety of needs and it is important to listen to what is important to them and get to know them in a genuine way. This allows for a unique and immersive perspective as a leader which can help inform important decisions about the company’s culture and policies. 

Adam: What are your best tips on the topics of negotiations and dealmaking?

Damon: To be a front-runner in the negotiation and deal-making arena, you have to be a great listener. Dealmaking is really about listening and understanding everyone around the table and what they’re trying to accomplish through the deal. The people that do it well articulate up front what their client needs and understand that they can compromise on all of the other details. The value isn’t to hammer out every detail, but to find a common ground and build from there.  

Adam: What are your best tips on the topics of mentorship? How can anyone find a great mentor and cultivate a successful mentor-mentee relationship?

Damon: I think of my mentors as my own personal Board of Directors. I really sought out a diverse group of people – across race, gender, background, expertise, and so forth. These are the people that I’ve learned specific areas of law from, or different areas of the business, etc. I’ve learned a lot from people that look like me, and I’ve learned a great deal from people who could not have been more different than me, and that diversity of thought, and perspective and background matters. I’ve approached mentorship in the same way. A few years ago, I wanted to get all of the people that I’ve mentored together around the holidays, and I was so proud of the level of diversity that I’ve invested in and who’s invested in me. It made me feel like I was in the right place and doing work that matters. 

Adam: What is the single best piece of advice you have ever received?

Damon: On the evening before a big job fair in which I had four interviews with prestigious law firms, my now late father who spent his career working hard building cars at a General Motors plant, gave me some incredibly poignant advice. He imparted wisdom despite his lack of specific knowledge about the intricacies of law firms when he said these three things: “1.) Wear your dark suit; 2.) Give a firm handshake and look them in the eye; and 3.) Be yourself. That's always enough!” I've been following this sage advice ever since and it's served me well. In fact, when I walk into a pressure-packed situation or have to deliver in a new situation (e.g., a board meeting or speech to a thousand people), I often close my eyes and say, "Be yourself. That's always enough."


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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