Female Leaders Making a Difference: Karen Freeman-Wilson

From her early days in the courtroom to her current position as CEO of the Chicago Urban League, Karen Freeman-Wilson's journey reflects the courage to rewrite the narrative. With courage and determination, Karen is writing the remarkable story of the female leader pioneering a new path from political arenas to non-profit governance. We hope her profound commitment to problem- solving, equity and servant leadership will inspire you to forge ahead on your own path.

Karen Freeman-Wilson, the pioneering Female Leader who went from political arenas to non-profit governance

In the annals of history, women have wielded their intellect, resilience and compassion to shape societies and catalyse change. From the suffragettes who fought for voting rights to the trailblazers who shattered glass ceilings, their indomitable spirit echoes through the corridors of time, inspiring generations to strive for a more equitable world.

Among these female leaders stands Karen Freeman-Wilson, a beacon of empowerment and progress in her own right. With a career spanning the law, governance and community advocacy, Freeman-Wilson’s journey mirrors the resilience and determination of those who came before her. As she navigated the complexities of public service, she not only broke barriers but also forged pathways for others to follow.

In the complex reality of leadership, Karen Freeman-Wilson’s story is a milestone in the enduring legacy of those who dare to make a difference and lead with purpose.

Today, I have the privilege to converse with the distinguished Karen Freeman-Wilson whose career trajectory has carved a path through the corridors of state and national government to the dynamic streets of city leadership, and now to the helm of an influential non-profit organisation, the Chicago Urban League. Her experiences have not only shaped the political landscape but also offer valuable insights into the interplay between gender, power, and public service.

From the Courtroom to the Community: Education, Giving and the Bedrock of Parental Support

Freeman-Wilson’s academic and emotional preparation began in the classrooms of Gary Public Schools, where she was nurtured by exceptional educators and mentors. Reflecting on her upbringing, she credits her parents for instilling in her the values of generosity and service. Her mother’s teachings on giving and her father’s lessons on enjoying life while making a difference laid the groundwork for her future endeavours.

How did you prepare yourself academically and emotionally to do what you do?

Regarding my academic and emotional preparation, I was blessed to attend Gary Public Schools and have incredible educators and mentors there. Dorothy Ford was our principal in elementary school, and I remember her being larger than life. Recently I saw her in Chicago and marvelled because she and I are the same height. I got a big chuckle from that. At every level of education, there were teachers who influenced me. I also attended Harvard College and Harvard Law School. I am proud to say I gained admission due to affirmative action and succeeded due to the foundation provided by the Gary Schools.

My ability to navigate a world distinctly different from Gary was by God’s grace. Emotionally, my parents laid a great foundation. Growing up as an only child, I was spoiled, but I also knew that I was blessed, I was taught that we are all blessed to be a blessing. My Mother was a giver and taught me to give. That always reminds me of the scripture in Luke 6:38. My Mother taught me how to live that scripture. My Dad taught me how to have a great time while doing it.

Pioneering Problem-Solver:  A Legal and Civic Odyssey

Can you share your career journey and how it led you to your current role as CEO of the Chicago Urban League?

 I began my career as a litigator–first as a Deputy Prosecutor and then as a public defender and private counsel. I spent time as the elected judge of the Gary City Court. I was also blessed to work at the state level as Director of the Indiana Civil Rights Commission and the Indiana Attorney General. I led a nonprofit, now called All Rise in Washington DC.

I credit my experience as a drug court practitioner and as CEO of All Rise as grounding my entire career in problem solving. So often, we focus on surface issues. In treatment court, we address underlying causes and I have approached my entire career that way. Additionally, experience at the local state and federal level equipped me to serve as Mayor of my hometown at one of the most challenging times in the history  of the city. All of this has given me great tools to lead the team at the Chicago Urban League.

Leadership Insights from Political Arena to the Non-Profit

What leadership insights have you gained from your diverse experiences in government and now leading a non-profit?

 As I think about my leadership journey, I have tried to never lose sight of the team and that God has placed me in positions for service. This is true even when I am the focal point as an elected or appointed leader. Each of us is only as good as our team. I have always believed in consensus building. Everyone should get to weigh in on decision making even though the leader may have the final say. You are getting the best decision and equipping others for leadership. Finally, I believe that the best leaders are excellent followers. I am not always leading. Whether it is the Sorority, professional associations, church or citizenship, I understand that it is important to be a good follower AND a good leader. 

A Leadership Philosophy of Caring and Serving

Can you articulate your leadership philosophy and how it has evolved over time?

 My leadership philosophy can be summed up in saying that people don’t care how much you know until they know how much you care. I also believe in servant leadership and that humility is more important than any other leadership characteristic because that equips you to learn from everyone and every situation. 

Forging Progress: Decisions at the Helm of Leadership

Can you provide examples of impactful decisions you have made in your various leadership roles?

As the Civil Rights Director, I led the team in educating legislators about the new Americans with Disabilities Act which allowed us to make Indiana the first state to become substantially equivalent with the federal government.  As the leader of a national treatment court organisation, I emphasised the importance of diversity in treatment courts so that everyone could have an opportunity at rehabilitation and a clean record.

As Indiana Attorney General, I led the team in prioritising health with the dollars from the tobacco settlement. As City Court Judge, our team started the first treatment court in the State of Indiana. This program created positive change for individuals addicted to alcohol and other drugs, their families and the entire community.  

As the first Mayor of Gary to govern after permanent property tax caps (an immediate 50% budget reduction), I led our municipal team in the development of diverse revenue opportunities and ensuring compliance with federal and state guidelines, for the first time in many years. We also restored the importance of civic engagement and transparency even when citizens might not like the news. We reduced the deficit from 17  mil dollars to 5 mil and gave it to the next administration to balance the budget but for the pandemic.  

As the CEO of the Chicago Urban League, I led the team in an agency turnaround while meeting the needs of the community during a global pandemic. 

Empowering Together: Our Community’s Collective Journey

How do you engage with the community in your current role, and what strategies have been successful?

In my current role with the Chicago Urban League, I engage with the community through our role as trusted advocates for the Black community, as the respected convener for the Black community and through programming in the areas of Workforce Development, Housing and Financial Empowerment, Entrepreneurship, Youth Services, and the IMPACT leadership program.  Some of my most enjoyable time at the League is spent with the community in events like the McDonalds Thanksgiving giveaway, our annual Back to School giveaway and our annual Gala with over 1800 people.  Each year we serve over 15000 people in Chicagoland. 

Navigating Gender Dynamics in Government and Leadership      

To start off, as a woman who has worked extensively in various levels of government, could you share some of the gender-specific challenges you’ve faced, and how have these experiences informed your approach to leadership?

 I have been blessed with amazing professional opportunities. Many of the roles like Judge, Attorney General, Mayor and Chief Operating Officer have been traditionally male. I have experienced gender bias in almost every role, however I understand God’s purpose in my life so I have not let people’s biases distract me.  I have felt it important to be very direct in addressing biased behaviour that has been overt. I consider it a teachable moment for me and all involved.  I think biased behaviour stems from ignorance. Other people’s ignorance makes me a more patient leader.

Transitioning Across the Spectrum of Public Service

Transitioning between governmental roles and the non-profit sector can be complex. Can you elucidate how your experiences in state and national government, and as a mayor, have influenced your approach to leading a non-profit like the Chicago Urban League?

 I have been blessed with amazing professional opportunities. Many of the roles like Judge, Attorney General, Mayor and Chief Operating Officer have been traditionally male.  I have experienced gender bias in almost every role, however I understand God’s purpose in my life so I have not let people’s biases distract me.  I have felt it important to be very direct in addressing biased behaviour that has been overt. I consider it a teachable moment for me and all involved.  I think biased behaviour stems from ignorance. Other people’s ignorance makes me a more patient leader.

Political Acumen as a Non-Profit CEO

Your political expertise—judge, lawyer, Indiana State’s Attorney General, Mayor of Gary, Indiana–  must be a significant asset in your current role. How has your political savvy played a part in enhancing the mission and effectiveness of the Chicago Urban League?

 My previous roles have all taught me the importance of collaboration. My experience helps me understand the availability of resources to assist our team in serving the community. For example, as Mayor I worked closely with the federal regional agencies in Chicago. When I arrived at the Chicago Urban League and had a meeting with the federal partners, it was like a reunion of friends. My prior experiences make me more effective at the League. 

The Lure of the Political Arena

After such a rich involvement in politics — do you find yourself missing the political arena, or does leading a non-profit fulfil a different aspect of your professional aspirations?

I don’t miss politics in my current role. For me it was a 12-14 hour a day job and I had little time for family or anything but city responsibilities. That was the reality of leading a city with many challenges. I have seen the resources that have been made available to cities after the pandemic and would have loved to have had that  financial support of our plan during my tenure as Mayor.  Now, I am content to allow others to pursue politics and am always happy to lend whatever advice or financial resources I can give. 

It certainly helps that I absolutely love my role at CUL. I work with an amazing team with corporate and government leaders who are very supportive of our work in the community. 

A Future of Balancing Personal and Professional Life

Lastly, managing a successful career across various demanding roles while maintaining a personal life can be a challenge. What is in your future? Do you have aspirations that are yet to be fulfilled?

 When I think about the future, I look forward to travelling and spending more time with my family. My youngest daughter will get married soon and I am now positioned to be more of a traditional grandmother. I also believe that my professional gift is solving challenging issues, so I want to continue to offer my assistance to cities, non-profit organisations, and other corporations.  

Thank you for taking the time to share your valuable experiences and insight. Your contributions to public service and your role in advocating for communities through the Chicago Urban League are truly commendable.

Looking ahead, Freeman-Wilson envisions a future filled with opportunities to continue her advocacy and problem-solving efforts. While she looks forward to spending more time with family and embracing her role as a grandmother, her passion for addressing societal challenges remains undiminished. Whether advising cities, nonprofits, or corporations, she remains dedicated to making a meaningful impact.

Karen Freeman-Wilson’s remarkable journey—from the courtroom to the community—serves as a testament to the power of servant leadership and unwavering commitment to social justice. As she continues to blaze trails and empower communities, her legacy will endure as a source of inspiration for generations to come.

Do you want to share your story and inspire our readers ? Know that  YOUR EXPERTISE is paving the way for a brighter, happier future.

Dr Shelley Fisher
Dr Shelley Fisher

Dr. Fisher believes that true leaders anticipate and initiate change, rather than waiting to react to external pressures. This proactive stance not only prepares organizations for future challenges but also empowers others to step into their own leadership potential.
Her commitment to leadership excellence is exemplified through her role as a speaker at various retreats and conferences, where she shares insights gleaned from years of experience. Dr Fisher has demonstrated an unwavering dedication to serving and uniting diverse communities.

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