Lisa A. Small Thompson (AKA, Legal Lisa)

What if the law wasn’t about winning, or losing, but about healing? What if justice wasn’t served in cold courtrooms, but in warm spaces where every voice matters? These aren’t hypothetical questions for this edition’s Woman Empowered, they are the foundation of her revolutionary approach to law and mediation.

In a world increasingly divided, where conflicts escalate and communication breaks down, our Woman Empowered has created something extraordinary: a legal practice that functions as a sanctuary. The Guest House Legal Options is a living testament to the possibility of resolution without division.

Her journey didn’t begin in legal lecture halls, but in the “why” of human behavior.

Lisa A. Small Thompson describes herself as “A rolling stone who has collected all these achievements,” but beneath the accomplishments was a young woman searching for her place in the world.

“I was that bookworm who spent a lot of time in the library,” she reflects. “I spent a lot of time exploring the lives of other people. I didn’t know who I was to myself, not knowing what I was able to do.”

This self-described, “shy, quiet one,” who was always observing and wanting to help would eventually transform her natural empathy into a powerful tool for conflict resolution, but first, she needed to understand conflict from the inside out.

Before Lisa ever entered the legal field, she logged years in high-stakes negotiation and crisis management. Working in airline and hospitality management, she faced daily crucibles of irate co-workers and unpredictable emergencies. It was there she discovered something profound; every argument contains two truths and a silent demand to be heard.

“I started seeing employees being ill-treated at the airlines, so I joined the union,” Thompson recalls. This experience ignited her passion for advocacy, particularly for women in positions of power. “I found out that there is power in numbers, especially when it comes to Black women in Toronto.”

A realization came during a pivotal moment in her life (fall 2012) while she was navigating a divorce. It was in this personal crisis that her legal future became clearer. The woman who once dreamed of dancing, who was told “There is no money in that,” and redirected toward computer technology, finally found her way back to what seemed her destiny.

What makes Lisa’s approach to law so revolutionary? It begins with how she views the legal system itself. What makes people clash? Why do simple misunderstandings metastasize into full-blown disputes? How can the hurt, the unheard, and the alienated find their way back to connection?

She never saw the law as a set of cold bylaws stacked on dusty courtroom shelves. For her, it was always a living, breathing space (a guest house) where the doors remain open to every story, every struggle, every soul in need.

This philosophy became the foundation for The Guest House Legal Options, a practice built on holistic, mindful, and culturally non-discriminative mediation. In her hands, mediation is a chance for: personalization, healthy communication, and even retreat. Clients may arrive angry, or lost, but they leave with their dignity intact, heard and whole. It’s a transformation that mirrors her own journey from uncertainty to purpose.

Behind every revolutionary is often an influential figure who shaped their worldview. For Lisa, that person was her father. “Even now, just the word father, brings back a lot of emotions,” Lisa shared. I heard the sadness in her voice as she continued. Her father, known as “Mr. T,” was a constable in Jamaica: respected, disciplined, yet gentle with his family. “He would take on other people’s children as his own. He was a God-fearing man,” Lisa shares.

He was also her first teacher and confidant. “He was my Google before there was Google,” she recalls. “Whenever I asked questions, he would feed it back to this; ‘Life trying to teach you something. If you don’t listen, you will go through it again.’”

This early lesson in reflection and growth became the cornerstone of Thompson’s approach to mediation and conflict resolution. It instilled in her a love for learning that continues to drive her work today.

With decades of experience guiding others through crises, how does Lisa process her own struggles? “Fear was one of my biggest hurdles,” she admits. “My fear was controlling a lot of things for me, and it was making it difficult to advance. I had to overcome fear, I had to champion fear, and get in front of fear, and know that anything I am afraid of, I had to deal with.” This confrontation with fear transformed not only her personal life, but her professional approach. “I am not afraid of confrontation anymore,” she says. “It is about changing perspective. It de-powered the fear element.”

This fearlessness allows Lisa to enter spaces of conflict that others might avoid, creating possibilities for resolution where none seemed possible.

Even the most accomplished among us have moments of reflection and regret. When asked which chapter of her professional life she would rewrite, Lisa doesn’t hesitate. “I would have rewritten the chapter around motherhood,” she says. “There were so many opportunities that I could have been more helpful to my children, and I would have paid more attention and care to the decisions that I made at those times. I would ask smarter questions.”

This vulnerability, this willingness to acknowledge imperfection, is perhaps what makes her so effective in her work. She understands that we are all human, all doing the best we can with the awareness we have at the time. “I did the best that I can,” she concludes. “I feel that.”

Lisa’s approach to law and mediation provides a model for how we might address conflict in our communities and our world. By treating the law as a “guest house” rather than a battlefield, she demonstrates that justice and healing aren’t mutually exclusive. By prioritizing listening over lecturing, understanding over overcoming, she shows us a way forward through our most challenging conflicts.

In a world that often seems more divided than ever, Lisa A. Small Thompson reminds us that the path to justice begins with a simple act: opening the door, listening deeply, and making space for every voice to be heard.

Her story isn’t just about one woman’s journey through law and mediation, it’s about the possibility of transformation, for us and our communities, when we approach conflict with courage, empathy, and an open heart.