In this interview, we explore the inspiring journey of Mary Ann Stiles, General Counsel at CCI Insurance and Founder of Mary Ann Stiles, P.A. law firm. Raised in humble beginnings, Mary Ann’s path to success has been marked by perseverance, hard work, and leadership in the legal profession. Through her experiences as the first full-time woman lobbyist representing the business community in Florida, she has helped shaped many laws in Florida but none more than the workers’ compensation laws and paved the way for many women in the field. Join us as Mary Ann shares her challenges, leadership style, and aspirations for the future. Discover how she has influenced the legal world and the legacy she hopes to leave behind.
Insights into Early Life
Mary Ann Stiles was born and raised in Tampa, Florida, as one of seven children in a modest family. Growing up in rural Hillsborough County without modern conveniences like electricity indoor plumbing, or running water, she learned resilience early on. Her father left school in the fourth grade to work in Kentucky’s coal mines, and her mother had little formal education. Despite these challenges, Mary Ann was determined to build a better life for herself. When she was ten, her family moved into the city, finally gaining access to basic necessities. This shift marked a new chapter for Mary Ann, but her early years instilled in her a work ethic and determination that would shape her future.
Role Models and Influence on Leadership Style
Books about inventors and world leaders shaped Mary Ann’s early sense of ambition. While working as a legal secretary at the age of 23, Mary Ann found a real-life role model in Bob Banker, an attorney who influenced her early legal career. Later, Jon Shebel, President of Associated Industries of Florida (AIF), became a significant mentor, teaching her about lobbying and leadership. At the time, there were few female role models in her field, but other influential figures like Attorney Ellen Davis and several colleagues at AIF helped guide her along the way. These individuals not only encouraged her but also shaped her approach to leadership, which was built on resilience and self-determination.
Challenges Faced and Overcoming Adversity
One of the most significant challenges Mary Ann faced was deciding to go to college and become an attorney at the age of 26, despite receiving little support from those around her. People from her socio-economic background, particularly women, were not encouraged to pursue higher education, especially not at her age. Nevertheless, Mary Ann pursued her dream, starting at Hillsborough Community College, while working full time, where a close friend, Dovree Broderson, encouraged her. She later graduated from Florida State University also working to support herself and went on to law school at Antioch School of Law supporting herself with work study monies, scholarships, and part time jobs. Along the way, Mary Ann faced criticism, especially as a woman trying to break into politics, but her determination never wavered. Her experience in workers’ compensation law and legislative work became a turning point in her career.
Defining Leadership Style
Mary Ann Stiles describes her leadership style as tough yet fair. She has always worked hard and expected the same level of commitment from her employees and colleagues. As a leader, she was generous in helping others, though some may have considered her too lenient at times. However, her experiences taught her to be understanding of the unique challenges that women, in particular, face in the legal profession. These principles—hard work, fairness, and compassion—have guided her decision-making throughout her career.
Qualities of an Effective Leader
According to Mary Ann, consistency is one of the most important qualities of an effective leader. She believes in teaching newcomers and listening to their concerns, recognizing that external factors in a person’s life may affect their work. Maintaining an open-door policy, being genuine, and being honest are central to her leadership philosophy. For Mary Ann, a successful leader must not only manage tasks but also understand the human side of leadership, especially when dealing with complex challenges.
Growth and Development as a Leader
Setting clear goals and striving to achieve them has been key to Mary Ann’s continued growth as a leader. Staying motivated and maintaining a positive mindset are essential elements of her leadership journey. In the future, Mary Ann aims to seek —n a aid board position at a large national company where she can apply her experience and leadership skills. By staying true to her values and continually evolving, she remains committed to making a difference in her field and beyond.
Mentorship and Supporting Emerging Leaders
Mary Ann takes immense pride in mentoring younger professionals, particularly women in law. She shared the story of a young lawyer in her Tampa office, Heather Byer Carbone recognizing her leadership skills early on and trusting her to manage the Jacksonville office. Under Mary Ann’s guidance, this individual went on to become a successful partner at a prestigious law firm. Another, Donna Remsnyder became a Judge of Compensation Claims. So did a male attorney Jack Weiss. Several others serve as partners in other law firms. Her niece Samantha Worthan used her training to continue work as a Paralegal for a well-known law firm. For Mary Ann, mentoring is about recognizing potential and providing the support and opportunities needed for others to thrive.
Balancing Professional and Personal Life
Achieving a balance between professional responsibilities and personal life is something Mary Ann learned later in her career. She admits that, for much of her life, her work consumed her time and energy, and it took her husband, retired NFL player Barry Smith, to help her realize the importance of personal time. Reflecting on this, Mary Ann emphasizes the importance of finding balance and prioritizing family, friends, and personal well-being, particularly for individuals in demanding careers. Today, she works part-time as General Counsel for CCI Insurance, enjoying the challenge of working with a young leadership team headed by Brad Dempton, Tobin Robeck and Kimberly Curry. She considers these leaders to be the brightest and most motivated individuals with whom she has ever worked.
Goals and Aspirations for the Future
As Mary Ann nears the end of her intense workaholic career, her goals have shifted. She plans to reduce her workdays to just one per week and hopes to secure a paid board position on a national board of directors. She also aspires to complete the autobiography she has been working on for the past decade. Personally, she looks forward to traveling with her husband and continuing their adventure together. Mary Ann takes extraordinary pride in her family, including her two stepchildren, Andrew Smith, and Amanda Smith and two grandchildren Andi and Walker and is excited to be able to spend more time with them.
Envisioning a Legacy as a Leader
Mary Ann hopes to be remembered as a trailblazer who made a significant impact in the lives of women. As the first full-time female lobbyist representing the business community in Tallahassee, she takes pride in seeing the increasing number of women in leadership and lobbyist roles within Florida’s Capitol. She also reflects on her contributions to workers’ compensation law, which improved conditions for both employees and employers. Mary Ann’s legacy is one of perseverance, dedication, and breaking barriers for future generations of women.
Staying Adaptable and Resilient in a Changing Industry
Adaptability and resilience have been cornerstones of Mary Ann’s success throughout her career. Today, she runs her own law firm, Mary Ann Stiles, P.A., with the help of her sister, Millie Stiles Reflecting on the importance of family support, she credits her sisters Millie and Glenda Stiles Lucontro for their unwavering encouragement over her entire odyssey to become an attorney and to become one of the top attorneys in Florida. In navigating industry changes and unforeseen challenges, Mary Ann believes that adaptability is key—embracing change and finding effective ways to manage it has allowed her to continue thriving in her profession. She learned that lesson the hard way.
Advice for Aspiring Leaders
Mary Ann offers simple yet profound advice for aspiring leaders: trust your instincts, work hard, and develop a “fire in the belly” that fuels your ambition. She passionately believes that, in America, it is possible to achieve success through dedication and perseverance, no matter one’s background. Having overcome numerous challenges herself, Mary Ann knows that success is within reach for anyone willing to work for it.
Reflecting on Success and Lessons Learned
Looking back, Mary Ann acknowledges that she should have diversified her investments and business interests sooner, rather than relying on a single client. However, she sees this as a valuable lesson learned too late in her career. To her, success is not just about professional achievements; it is about balance, personal fulfilment, and being surrounded by loved ones. She measures her success by the impact she has made on others, particularly the women who have followed in her footsteps and the family she cherishes.
In conclusion, Mary Ann Stiles’ remarkable journey from her challenging upbringing to becoming a trailblazing figure in law and leadership serves as an inspiring testament to resilience and determination. Her dedication to breaking barriers, mentoring future generations, and leaving a lasting legacy reflects her profound impact on the industries she has shaped. Through her unwavering passion and commitment, Mary Ann has not only achieved personal success but has also paved the way for others, demonstrating the power of perseverance and the importance of giving back. Her story is a powerful reminder that with courage and vision, true change is possible.
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