“Get Inspired” Throughout Your Life Phases with Cherylyn Harley LeBon

By: Brittany Maroney


In 2010, women made up 31% of the legal profession. By 2020, that number had climbed to 37.6%, with consistent gains for the last decade. As more women join the legal profession, the industry is seeing a growing diversity in terms of new perspectives and leadership that guide our regulatory and legal issues here in the United States and internationally. 

One of those brave women leading the charge is Cherylyn Harley LeBon, currently a Partner at the prestigious Dunlap, Bennett & Ludwig law firm. On November 17th, Par and Punchh invited LeBon to share more about her inspirational life as a woman in the legal profession, along with her advice on balancing family, a career, and a positive outlook. 

With a history of working with a vast array of businesses and government contractors across the country, LeBon brings to the table over 20+ years of legal experience with companies nationwide, along with experience in Washington, D.C., as a high-ranking official at the Small Business Administration (SBA), the Department of Veterans Affairs, and as lawyer in the U.S. Senate and U.S. House of Representatives. Her specialty? Providing guidance to companies of all sizes on business legal affairs, including entity formation and structure, corporate governance, and navigating the federal and regulatory environment.

When asked on how she was initially attracted to the legal profession, LeBon shared that it all began in a constitutional and political science class in an undergraduate class. 

Shares LeBon, “[I found that] the intersection of public policy and the law, was just fascinating, and I was immediately hooked. How public policy, decisions, and regulations were made and more specifically how they impacted people and the world we live in.”


From there, LeBon grew her career, first traveling internationally, before settling for a time in Washington D.C. Speaking four languages, LeBon was able to support a Prime Minister Candidate, as well as spend time working at a large German company. Her eclectic past has given her unique insights into both cultural diversity and sociolinguistics. 

“On many different levels, exposure to different cultures always has amazing benefits. I think working among different professional cultures is very humbling because no matter how fluent you’re still speaking another language, and frankly, it is just hard to say everything perfectly, every day,” explains LeBon. “There are these cultural nuances that I always say just keep you honest. Holistically it was just such a great learning experience for me.”


LeBon also spent substantial time working in Congress. During that time, she worked as a counsel to a member of Congress and served as liaison to the Education and Workforce Committee.

“My] former boss was also a leader in Congress on African issues,” explains LeBon. “So, I often collaborated with diplomats and African leaders from all over the world. One of the most pivotal and exciting issues that I worked on was the passage of NAFTA as a young lawyer in the 1990s. I also was a Senior Counsel on the U.S. Senate Judiciary Committee, a position that had me dealing with issues including the confirmation of federal judges and Administration officials, major business legislative and regulatory matters, and human rights issues.”  

I also joined the Committee a few years after 9/11, and this Committee dealt with some of the post-9/11 legislation, very hot button, timely issues of the day, as our country was shifting to a more national security role.

Serving in the George W. Bush administration, I was a presidential appointee at the Department of Veterans Affairs and the Small Business Administration. I would walk into the White House, saying wow, I am in THE White House. How amazing is this? And to be in the presence of the President of the United States, there’s so much I could say about these positions, but I want to leave you with the point that it was incredibly humbling.”


Throughout her career, LeBon admits that work life balance has not always been easy for her and that the key to her success has always been adapting to her life circumstances. 

“That question of work-life balance is a question many people deal with. One of the things that I learned early on in my career is that you have to view your life in stages and to be willing to be flexible depending on your priorities at that time of your life,” says LeBon. “For instance, when my children were very young, I was able to work full-time at a pretty demanding job working for the President of the United States. When they started school and my priorities shifted to after-school pickup and homework, I knew it was time to refocus. I formed my own company and built a business that enabled me to have more flexible working hours.”

LeBon’s new business was an immediate success, allowing her to support other growing businesses nationwide and provide counsel on regulatory compliance, growth strategies, and risk management. As her children got older, she was able to take on even bigger clients and travel more. She realized another phase of her life was upon her and she eventually moved to Dunlap, Bennett & Ludwig, and joined as a Partner in the Corporate and Government Contracts practice.


LeBon readily admits being humbled by the many opportunities she has been given and she always takes the time to truly appreciate and absorb from those around her. In fact, her quest for advice and guidance has allowed her to easily move through phases in her career by asking others and mentors, as they navigate their own journeys.

“I always say, don’t be afraid to ask people for advice. As I navigated those different stages in life, whether it be my career or other opportunities, I always look around and find those that are in the next phase, and I take the time to ask what is working and what doesn’t,” explains LeBon.

She also thinks this will help other women evolve in their careers; that opening ourselves up to asking questions and adapting our styles is helping grow organizations and leaders. 

“I think the concept of leadership has shifted in the last 20 years, away from a more autocratic style towards a much more collaborative approach, one that fosters productivity, innovation, and much more creativity,” says LeBon. “If you think about a collaborative style, these are already wonderful qualities that women possess, and therefore it can eventually help more women achieve leadership roles.” 

One book she recommends for fellow female leaders is “The Leadership Lab” by Chris Lewis and Pippa Malmgren. It talks about how leadership has evolved and the evolution of leaders on an international scale. Lewis and Malmgren guide readers through a theory on why individuals just are not accepting this autocratic style anymore. Society now wants leaders who are collaborative and creative, fostering teamwork that just makes sense.

To LeBon, this is the opportunity women have needed. The one that will help more women navigate their own professional and personal phases of life, opening doors and granting them the opportunity to lead. 

Our heartiest gratitude to Cherylyn Harley LeBon for all the wisdom that she provided in last week’s “Get Inspired” series. If you would like to learn more about PAR + Punchh’s WIT program or attend a future session, feel free to visit us at punchh.com/women-in-tech/

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