Monica Caldas of Liberty Mutual Insurance: People listen to every word you say, so be careful that you don’t send an inadvertent message

…people listen to every word you say, so be careful that you don’t send an inadvertent message; you are human and need to take breaks/vacations and organizational health is step one in building a strategy, so pay attention to that first.

As a part of our series about strong women leaders, I had the pleasure of interviewing Monica Caldas, CIO, Global Retail Markets, Liberty Mutual Insurance.

As the Global CIO of Liberty Mutual’s Global Retail Markets, Monica brings cross-industry experience to the global stage to lead as a change agent. Monica’s most critical mission is to unify an operation that has grown through 20+ acquisitions over the last decade and historically operated autonomously. She unites employees across 15 countries and relies on her transdisciplinary training in operating technology, solving problems using data and executing change in complex global economies to deliver business model innovation through a robust digital strategy.

Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I think about my career as a set of foundational building blocks.

The first is that I developed an early interest in problem solving as a child; watching my immigrant parents make their way in the US without education and many resources. It taught me how to be resourceful and hardworking and that no problem is too big to overcome.

When I went to college, I developed a passion for technology and how computers could solve problems quickly, automate and process logic quickly and I chose to pursue my first job out of college in a Technology Leadership training program at GE that pushes the limits of problem solving with technology. It was an energizing job that kept me glued to the journey of a technology leader that looks to solve problems.

Subsequently, I selected and was chosen for roles that had big complicated problem statements across various industries and parts of the world. I never shied away from a challenge and I was lucky to have mentors and sponsors that were there to guide or give me feedback. I learned to listen and keep adjusting, thus the concept of continuous learner.

Ultimately, I can summarize it as four key ingredients. A combination of 1) a love of solving problems 2) gaining experience in many aspects of technology to get a wide range of hands-on exposure, 3) a wide network of mentors and 4) a willingness to take risks and go do the jobs that others did not want to do.

Can you share the most interesting story that happened to you since you began leading your at company?

In my first 12 months, I traveled to 18 global sites to meet my team and functional partners in person. Also, to understand deeply the local context of how we operated in the market. One of my trips was to Bogota, Colombia. In this trip, many people made a comment on my last name being associated to a region of Colombia. Being that I am a native of Portugal, I was surprised. Upon further inspection, my last name is three times more frequent in Colombia than in Portugal. It was interesting to learn this and when I have more free time, it will be a good heritage research project to take on!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I first started, my funniest, and unfortunately frequent mistake, was getting lost in the facility. I would be navigating the Boston campus looking for my next meeting and in the first two weeks, I think I was escorted by a kind colleague almost every time. I learned early in my career to ask for help, so it’s a good reminder that it applies to all aspects of life.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CIO or executive that most attracted you to it?

It is very rewarding to apply technology in meaningful ways to solve problems and grow ideas. I love the fluidity in the type of work that sometimes brings me deep into transactions and problems, while other times I spend time on the big picture and get to design the future and chart the course forward. Finally, it is inspiring to grow teams and leaders. To help develop a culture that endures.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

The difference is how you spend your time. I think any leadership position requires the person in that role to focus on developing people and ensuring the work we do is connected to the outcomes we are trying to achieve. When I moved into executive roles, my scope was wider, so I had more levers in which to drive results. The role involves helping to implement solutions or rolling up the sleeves to help the team problem solve or make choices about the best approach. However, most of my time is spent coaching teams to enable them to drive change. I also spend a significant amount of time thinking and planning transformation via technology solutions and leading problem-solving sessions about innovations we can bring to our business to transform how we operate.

What is the one thing that you enjoy most about being an executive?

I enjoy growing teams and driving change through coaching. I like helping to bring people together and role modeling thought leadership that enables people to openly challenge the status quo — the concept of “what got you here, won’t get you there.” It’s ultimately about propelling our organization forward.

What are the downsides of being an executive?

Finding ways to balance and create the space to re-energize is hard in any occupation, but it is a downside to the executive level roles. We often talk about balance, but it is frequently elusive. The best analogy I have heard is, “think of life as a stove with burners that are on (family, health, work and friends)”. Sometimes one needs to be turned up, but instinctively, you need to balance. You need balance and take the time to recharge regularly, not just once a year. Do it daily. As a result, I have improved my meditation practice.

What are the “myths” that you would like to dispel about being a CEO/CIO or executive. Can you explain what you mean?

We don’t have all the answers. I have been in roundtables with early career technologists who ask how it is possible to get to the CIO role when technology changes so fast. My response is that every leader needs to be a continuous learner and it is a myth that to be a CIO or any other executive you need to know all the answers. Instead, you must be a continuous learner and know how to ask questions and build teams that can work together to solve problems based on each other’s knowledge, not based on one person’s knowledge alone.

What is the most striking difference between your actual job and how you thought the job would be?

When I started in executive roles about eight years ago, I thought I could find more time to strategize, read and think about the future. However, the reality is that time is elusive. I had to adjust my routines to create space for thinking/contemplating first thing in the morning when I wake up because free time is hard to come by. The course of events throughout the day evolve and demands on the schedule are high.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

The traits of an executive include high level of satisfaction in engaging with people regularly and gaining energy from complex problem solving, while at the same time, having courage to set paths that have not been previously defined. Someone who prefers solitude and routines that don’t deviate will probably have difficulty in the fast-paced executive level roles.

What advice would you give to other female leaders to help their team to thrive?

Helping teams thrive should not be any different if you are a female or male leader. The components of helping teams grow and building the right teams are the same. It’s about human interaction and the intersection of diversity of thoughts and experiences with skills. Also, it is about balancing between feedback and coaching at the individual level so that you grow leaders and set people up for success.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My career started at GE where I applied my courage and grit mindset and developed bold leadership. I was lucky to work with terrific mentors and role models, and much of their advice has stayed with me to this day. However, one specific role model was Martha Poulter. She was a University of Connecticut graduate like me, from a Hispanic background, leading technology for a large organization, all while making bold moves to position our organization for growth. I was impressed by her humility and leadership. By having a front row seat, I learned that you must lead with humility and be a continuous learner that seeks to discover from those around and outside of your organization so that you have the wisdom to make difficult calls.

How have you used your success to make the world a better place?

I use my success to inspire more girls to pursue careers in STEM. Throughout my entire career, I have been engaged in affinity networks both inside the company and in the community. I believe it is important to role model and encourage girls to get involved with technology. At my previous company, I sponsored a global program that engaged middle school-aged girls through summer camps in STEM. In my role with Liberty Mutual, I am engaged in a similar program.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

The biggest thing that I wish someone told me before I started CIO roles is that it is hard to know what is really going on. We are flooded with information that is mostly curated. The informal channels where you can connect with team members to get more context become more guarded and it’s a balance to go seek information without undermining key reports. Thus, it is important to create time and venues like roundtables and seat rides to get closer to the process.

The other things I wish someone told me — people listen to every word you say, so be careful that you don’t send an inadvertent message; you are human and need to take breaks/vacations and organizational health is step one in building a strategy, so pay attention to that first.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I would focus on the movement of gender equality. The World Economic Forum has calculated that it will take women almost 100 years to reach gender equality. I would focus on the outcome of improving equality to yield better quality of life, but I would focus on tackling the processes that lead to the situation of today, like education and social biases.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The best quote that I have carried since college is from Will Rogers, “Even if you’re on the right track, you’ll get run over if you just sit.” It is about taking action and moving forward. I started as an immigrant child watching my parents pursue the American dream and the obstacles they faced by not fitting into the mold of others around them. They showed me that you must have grit and you live with this philosophy that “failure is not an option.” There is always a path — you just have to find it. I learnt courage and to not fear failure. Thus, I always look at my journey and ask myself if I am tackling the challenging problems or am I just sitting down watching the world go by?

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Sheryl Sandberg. I admire her success and to me, it appears that she is an authentic leader who knows how to build teams, how to drive change and how to transform operations. From a personal perspective, she is a woman role model in the tech industry and vocal about how women can succeed and need to advocate more for themselves while simultaneously calling out for men as allies to help mentor and sponsor more women in STEM.

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