Leading with Heart: Theresa Mason of American Share Insurance On The Power of Authentic Women’s Leadership

An Interview With Pirie Jones Grossman

Inclusivity of thought is important. You can’t be authentic without including varying views and opinions — that’s what makes you grow. It doesn’t mean decisions won’t be made that are contrary to input, but it means you’ve considered those viewpoints in your decision-making process.

In today’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Theresa Mason.

Theresa Mason serves as the Chief Executive Officer of American Share Insurance, a private deposit insurance company committed to protecting credit unions since 1974. Prior to her current role, Mason spent 16 years with Grange Insurance and the Kansas City Life Insurance Company where she directed highly effective finance, operations, sales and IT teams. Mason is a CPA and also carries her CMGA (Chartered Global Management Accountant). She also holds affiliations with the American Institute of Certified Public Accountants (AICPA) and the Ohio Society of CPAs.

Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Before I joined American Share Insurance (ASI), I was working at a property casualty insurance company. I am someone who is always eager to expand my horizons and take on new challenges, and I was at a true inflection point in my career.

When the opportunity with ASI arose, it reconnected me to my childhood. My dad worked in the railroad industry his entire life and was actually insured by American Share Insurance — talk about a full circle moment! In fact, I still have my credit union passbook from when I was five years old.

The credit union was integral to my family while I was growing up — when my father was sick and couldn’t work and we needed a mortgage on our house, the credit union was there. You hear these stories every day of how credit unions have helped communities and families, and I wanted to be a part of continuing this mission.

It almost felt like fate when I was given the opportunity to lead American Share Insurance. I am honored to spend my time working with the very credit unions that have paved the way for so many families like my own.

Can you share the most interesting story that happened to you since you started your career?

**Theresa thinking on this one

Many interesting things happen to you over the course of your career, but some stick out to you. For me, getting to this point of my career has been a blend of working with amazing people and a family that has supported me along the way. That doesn’t come without a foible or two. I remember working late and being on pick-up duty. I was just trying to get one more thing done, and I was running to pick up my kids from swimming practice. Cell phones were new, and I certainly didn’t appreciate all they could do, but my kids did. I got a call from my son asking where I was because practice was over. I told him I was on my way, to which he then asked me why my location showed that I was still at work. Busted.

It’s not always easy balancing my career and my home life, but I’ve always allowed my kids to be privy to what’s going on at work, especially during the difficult times that might require me to be less present at home. Honest conversations have gone a long way in building our relationships.

What do you think makes your company stand out? Can you share a story?

Our company stands out because we are the only organization in the U.S. that offers private deposit insurance for credit unions. Simply put, we allow so many credit unions around the country to exist and continue doing what they do best — serving their communities. We have the unique ability to create innovative and agile solutions to complex issues.

Take for example the Silver State School District in Nevada. While this was quite a while ago, the school system came under financial strain in 2008. We were able to not only get them back on track but help them thrive in ways they hadn’t experienced before. At our crux, that’s what we do. We’re here for the people that need us and help them to be stronger and better than they were before.

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Grit: For me, grit isn’t about talent. Grit isn’t about luck. Grit isn’t about how bad you want something. Instead, it’s really about what some researchers call an “ultimate concern” — a goal you care so much about that it gives meaning to almost everything you do. Without this inherent grit, I wouldn’t be where I am today. It’s the driving force behind any success I’ve encountered in my career.

Integrity: Honestly, I never thought that I would be “the leader” — I have a hard time looking at myself that way. I still sometimes have to pinch myself when I look at where I’m at. But, no matter where I’ve worked or what I’ve done, I’ve always pushed for quality over quantity, for integrity, and for authenticity with my colleagues. And that has earned me the opportunity to lead, which is something I don’t take for granted.

Being Inquisitive: Asking questions is the best way to uncover the information you need to move forward. I’m notorious for asking questions — in fact, I’ve been told that no one asks as many questions as me…and honestly, that’s a badge I’m happy to wear.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Before I joined American Share Insurance, I led a company that was in the process of being purchased. Boy, can that be a scary time for folks. And, honestly, it was really scary for me personally. Was I going to lose my job? Was I going to need to find another way to support my family? All of these questions ran through my mind.

But, as a leader, I had to put those personal concerns aside and focus on my team. If I was feeling anxious, I couldn’t even begin to imagine how they were feeling. And once I made that decision, I went full force ahead in getting questions answered, disseminating information, and ensuring that I calmed fears as best as possible. While there was a lot we didn’t know, there was a lot that we DID know.

So, I spent weeks negotiating and trying to meet the needs of our people. I worked to manage facts versus emotion and get everyone comfortable with the uncomfortable. I’m proud to say that within that first year of being sold, we didn’t lose a single person. People stayed on board without jumping ship out of fear.

I still look back on this experience with an immense amount of pride. I was able to understand the needs of my current colleagues while working to address the issues of the company that was coming in to acquire us. It was certainly a humbling time that has shaped how I lead today.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?

Coming from a finance and CPA background, I’m used to delivering facts — things like “this is your revenue, this is your income.” I lived in a very black and white world, and it’s all I knew.

When I moved into a new role of leading a life insurance company before I joined ASI, my world become a lot grayer. This was especially visible during Covid. Leading a life insurance company during an unprecedented pandemic is jarring…and quite humbling.

I still remember receiving our very first claim during Covid that involved an elderly couple in a nursing home. One passed away from Covid, and the couple wasn’t able to see each other before this tragedy happened. It was truly a difficult moment for all of us. I vividly remember bringing my team together and telling them that while this was not a “rah rah” moment, it was a moment of significant poignancy to try and balance work, fears, emotion and hearts. We were essential workers of a different type during the pandemic — perhaps not the type you find in hospitals, but the ones who helped the survivors to continue living when their loved ones were gone. It was incredibly important for my team to lean into their emotions while also getting the job done for those that needed it most.

Traditional leadership might tell you to stick to the script, stay the course and not show emotion. I did the exact opposite and chose to lead with empathy during a time of extreme fear. It’s changed the way I communicate and has made me a better leader.

In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?

There was someone in my previous organization who passed away from cancer. She had been at the company for over 30 years, and while I hadn’t known her very long, she was one of those employees that was synonymous with the organization. They just went hand-in-hand, so losing her was truly monumental for everyone.

This is where a very delicate and empathetic balance needs to come into play. I needed my team to know that I deeply cared about their relationship with her, and I needed to allow them the space and time to mourn her death, even if that came as a cost to company operations. Did some people think that maybe that was “too much?” Perhaps. But did I let that change my course? Absolutely not. It was more important to me to give my team the space to mourn and heal so that they could come back stronger when they were ready to do so — and they sure did.

Resilience and vulnerability go hand in hand, and when properly balanced, they can be your superpower.

As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?

Too many times (I don’t have enough fingers to count!), I’ve seen males go for the jugular to show their dominance. It becomes dog-eat-dog…almost like a match. I’ve never approached things this way. I’d much prefer to implement a strategic leadership style that is collaborative and allows others to come alongside me.

For example, if I don’t agree with something that’s being proposed, I’ll often say “I don’t quite understand that. Can you share more?” This way, I’m encouraging and allowing a two-way dialogue that helps me to get to my end goal rather than sending that other person into full attack-mode. It’s never good to question someone’s theory or logic- it’s better to engage in conversation. And most times, when I approach things this way, I get the same result as the “jugular” route but in a better, more collaborative way. Or, sometimes the conversation will be the impetus for an entirely new approach.

It can be difficult to work somewhere where you aren’t heard or don’t feel like you’re impacting change. Then, it just becomes about clicking your timecard and going through the motions. That is not who I am. I need to work in an environment where opinions are not only heard but encouraged. And, as a female leader, I strive to demonstrate this every day.

How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”

Anytime I ask a question, I don’t give my answer until everyone else around the table has been able to give input. At previous companies, I’ve seen that some questions were not being asked, rather answers were being dictated. I’ve worked hard to create a cultural shift here that allows for meaningful dialogue.

It’s interesting, but many times I’ve seen that there is some kind of dominance that takes place when a new leader comes in — a “it’s my way or the highway” type of approach. I want to make sure that people understand that I want to create a safe space for sharing thoughts and opinions. That doesn’t mean I don’t have my own answer, but it means that my answer may shift based on collective input. I certainly don’t want my way of thinking to drive every company decision — I welcome feedback and different ways of thinking as that’s always when the best ideas and solutions come to life.

The financial industry can be pretty traditional. It’s my goal to learn from and respect the past while reshaping the future through new ideas and insights.

What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?

It has given me wings to fly. I’ve grown the most in my career when I’ve had a mentor in my corner. It’s given me the support I’ve needed and has allowed me to gain confidence in my abilities, all while providing me with challenges that consistently push me to be better. When I think about my mentors, I’ve been very intentional — I look for someone who is authentic with very diverse views on leadership styles. It helps me hone in and find my own authentic sweet stop.

I’ve kept strong relationships with several of my bosses, but the last CFO I worked for is someone who has served as an invaluable mentor. Whether it’s brainstorming ideas or talking through significant career moves and changes, she’s been there for me. She’s always asked me great questions, and rather than giving me an answer, she’s allowed me to talk through it and arrive at an answer that I think I knew all along but needed the extra push (and extra discussion!) to get there. I hope she knows how important she is to me, and I’m grateful to have someone who continues to be not only a mentor, but a friend as well.

Based on your experience and research, can you please share “5 Ways Leading Authentically as a Woman Will Affect Your Leadership”?

If you’re authentic, your leadership will be, too. Here’s some things to keep in mind.

1. Be true to who you are. For me, that means not playing games and pretending you’re someone that you simply aren’t. This type of approach is appreciated by my peers and bosses alike. I am who I am. That is how I was promoted to my first role as a President. Yes, I was qualified, but you knew what you were getting, and people can depend on that.
2. Build a foundation of trust. If you can do this, people will come to trust you and what you have to say, even if that’s saying that you don’t have an answer (that can be hard for many leaders to do). We’re expected to have all the answers, all the time. And that’s just not possible. That also means you’ll have to rely on your team and trust them, too.
3. Being candid is king. Say what you mean and mean what you say. This will require you to be more prepared and less “off the cuff” because you’ll need to think about different questions you may get asked, who your audience is, and how you’ll respond. When my previous company was sold, I had to be really intentional on how I responded to questions while also ensuring that those in my company felt heard. Building that takes thoughtful, transparent communication.
4. Be engaged and be committed. When I came to American Share Insurance, I was really overwhelmed. It was a new company and a new industry, so I was just going through the motions and checking boxes off the list. That’s not who I am, so I dug deep — I found new and exciting ways to connect to this industry, which allowed me to be engaged and committed to the credit union movement in ways I didn’t think were possible. If something is just a “job” to you, it will never work.
5. Inclusivity of thought is important. You can’t be authentic without including varying views and opinions — that’s what makes you grow. It doesn’t mean decisions won’t be made that are contrary to input, but it means you’ve considered those viewpoints in your decision-making process.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

Of course. If you’re an empathetic leader, people may perceive you as weak, indecisive, not qualified, and only making decisions by committee. However, it is just the opposite.

These can be addressed by letting people know that input is invaluable, and that leading with both your heart and your mind will land you in the right spot almost every time.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 😊

I am passionate about financial literacy, especially at the high school level. Mortgages, 401(k)s, lease vs. buy, put it on a credit card or pay cash — these are decisions all of us are faced with every day, and over time, they add up significantly. My own children have very fundamental questions about these topics since they weren’t taught in the classroom. Learning the hard way can cost people valuable resources that are scarce — time and money. I would love to find a way to help our youth become more financially responsible, and more than that, financially confident. While I know things like a checkbook are becoming obsolete, it’s critical that we teach younger generations to check in on their finances, as well as give them a place to turn when they need guidance.

How can our readers further follow you online?

You can follow me on Linkedin HERE. Make sure to also check out ASI’s website — I promise you the world of private deposit insurance for credit unions is really fascinating!

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About The Interviewer: Pirie is a TedX speaker, author and a Life Empowerment Coach. She is a co-host of Own your Throne podcast, inspiring women in the 2nd chapter of their lives. With over 20 years in front of the camera, Pirie Grossman understands the power of storytelling. After success in commercials and acting. She spent 10 years reporting for E! Entertainment Television, Entertainment Tonight, also hosted ABC’s “Every Woman”. Her work off-camera capitalizes on her strength, producing, bringing people together for unique experiences. She produced a Children’s Day of Compassion during the Dalai Lama’s visit here in 2005. 10,000 children attended, sharing ideas about compassion with His Holiness. From 2006–2009, Pirie Co-chaired the Special Olympics World Winter Games, in Idaho, welcoming 3,000 athletes from over 150 countries. She founded Destiny Productions to create Wellness Festivals and is an Advisory Board member of the Sun Valley Wellness Board.In February 2017, Pirie produced, “Love is Louder”, a Brain Health Summit, bringing in Kevin Hines, noted suicide survivor to Sun Valley who spoke to school kids about suicide. Sun Valley is in the top 5% highest suicide rate per capita in the Northwest, prompting a community initiative with St. Luke’s and other stake holders, to begin healing. She lives in Sun Valley with her two children, serves on the Board of Community School. She has her Master’s degree in Spiritual Psychology from the University of Santa Monica and is an Executive Life Empowerment Coach, where she helps people meet their dreams and goals! The difference between a dream and a goal is that a goal is a dream with a date on it!