Often life’s greatest blessings are found in its detours. We plan a path and life presents us with moments of growth, both encouraging and challenging, that lead us away from those plans into a life that is more rewarding than we could have imagined. T. R. Williams knows this experience all too well. The new Senior Director of Development at the United Way has taken a path that, though winding, has divinely directed her into a rich life in Madison that she did not anticipate.
Williams is a proud Milwaukee native that has Madison home. She left her home in Milwaukee for the first time when she went to Vassar College in Poughkeepsie, New York to pursue a degree in Political Science and Africana Studies. She returned to Wisconsin to attend law school at the University of Wisconsin-Madison. After finishing in 2013, she encountered her first professional detour when she chose to work in Milwaukee instead of following her plan to return to the east coast. She practiced family law and was an assistant state public defender for a few years before stepping away from legal practice to coordinate alumni and student engagement for Milwaukee Public Schools.
While at MPS, Williams participated as a fellow in the Wisconsin Women’s Network Policy Institute. This experience changed her trajectory. She made her greatest career shift to date when she accepted a position as Advocacy and Government Relations Specialist for the Wisconsin Primary Health Care Association in 2018, which brought her back to Madison. Williams remains connected to the Wisconsin Women’s Network as the Policy Institute’s lead facilitator.
The position with the Wisconsin Primary Health Care Association brought Williams fully into the lobbying space. As one of the few Black women registered lobbyists in the state, Williams describes her work there as “blocking and tackling at the state and federal level on behalf of the federally qualifying health centers in Wisconsin.” These centers are commonly known as community health centers. She led a diverse coalition of organizations and advocates to bring dental therapy licensure to Wisconsin.
As a lobbyist, Wiliams was a fixture in the State Capitol. When Governor Tony Evers was elected in 2019, he selected Williams to serve as the Deputy Director of External Affairs for the State of Wisconsin. She declined. She enjoyed her lobbying work and did not see herself making another shift so quickly. After a candid conversation with her mother, Williams changed her mind and decided to lean into another detour. She was able to accept the opportunity and began working in the Governor’s Office in January 2020.
Just 2 short months after moving to the Governor’s Office, COVID changed the nature of Williams’ work. Evers deployed her to the State Emergency Operations Center. She was part of “Operation Checkmate,” the Community Resilience and Response Task Force that created policy, plans, and standards for congregant living settings such as carceral facilities, nursing homes, and other places where multiple unrelated people dwell together.
Williams’ work with Operation Checkmate caught Evers’ attention, in 2021, he elevated her to Assistant Deputy Secretary in the Wisconsin Department of Health Services. She served there until Evers’ first term ended in 2023.
After leaving the Governor’s Office, Williams thought that her next step would be a more national role, so she took her lobbying skills back to Boston to work for a health startup. But she missed Wisconsin and decided to return.
This detour thrust Williams into the world of entrepreneurship. She founded TRWConsult414, LLC, a boutique agency supporting small nonprofits who cannot afford a lobbyist. She pairs her lobbying expertise with a love of teaching to help these organizations to understand the policy making process and develop an advocacy strategy.
In 2024, a colleague reached out to Williams to ask her to serve as a Loaned Executive and Campaign Fundraising Specialist for the United Way of Dane County. A loaned executive is a temporary employee who is borrowed from a company to volunteer as an ambassador for a nonprofit. Williams shared her United Way story to encourage giving. This position gave her a taste of development work, and she came back for more in summer 2025. But when she returned, there was a position open for a Senior Director of Development. Williams followed this detour into her current position, which she began in September.
While some may perceive her career as disjointed, Williams sees a throughline connecting the practice law, lobbying, and development. She says, “There is a platform and an invitation to use the power of words, which I think is art, to encourage someone to see things the way that you see them. I think that’s a unique platform to have.” She sees this opportunity in each facet of her career, which has allowed her to continue growing and to maintain commitment to her core principles. Through these turns, she has developed a tenacity that helps her to endure the inevitable losses in law, lobbying, and development and to savor the wins.
Williams is clear that Milwaukee is responsible for helping her to build this tenacity. Her pride for her hometown is palpable. While her parents now live in Hartford, Wisconsin, she visits Milwaukee consistently to spend time with her sister, brother-in-law, and her two favorite people, her 13-year-old niece and 6-year-old nephew. Family is Williams’ bedrock. She describes herself as “a Daddy’s girl and Mama’s baby,” but it is clear from her conversation that her favorite role is “Tee Tee.” “They force me to lock in,” she says. “I look forward to seeing the world through their eyes.”
Williams’ professional life is full of interactions with people that can feel all-consuming. Since making Madison home, she has made a concerted effort to expand her personal circle. She joined the Madison Metropolitan Chapter of the Links, Inc. and is preparing to celebrate 1 year as a member of Alpha Kappa Alpha Sorority, Inc. this month. She has also built connections with “dope people with dope organizations” like the YWCA of Madison, The Foundation for Black Women’s Wellness
Williams was surprised by the number of Black Madison natives. She recognizes the university and companies in the city who made investments to the 1970s through the 1990s to recruit Black talent to graduate school and professional positions, which has led to a new generation of Black Madisonians.
While she likes the pace of Madison and venues like the Black Business Hub and Café Coda, she sees the problem of recruiting and retaining Black talent in Madison as an issue of quality of life. “What kind of life can people build here?” she asks. She describes racism as “potent” in Madison and longs for a time when Black people will be able to occupy public space in the city without being watched or questioned. At the state level, disparities in infant and maternal mortality rates and incarceration also make Wisconsin feel inhospitable for Black people. “It really thumbs the nose at our credibility and authenticity in trying to be a space for all Wisconsinites.”
Looking ahead, Williams plans to continue bringing the fullness her vast experience and focused work ethic to her development work at the United Way. “I am excited to do my very best. That’s what my family and my faith have taught me to do.”
