During Assistant Principals Week, AFSA is featuring profiles of some of our outstanding assistant principals.
William James Conroy—known as Billy—is an assistant principal fluent in English, Portuguese and Spanish. “I have a predisposition for language,” he says, a trait that has shaped his career in multilingual education. But his path to school leadership was anything but predetermined.
Born and raised in Bridgeport and Stratford, Connecticut, Conroy developed an early love for language and the arts. At home, his Portuguese-born mother and grandmother spoke to him in Portuguese, while his Irish American father and extended family created a nurturing environment that encouraged creativity. He painted scenery, wrote stories and explored his imagination—an important refuge during a difficult childhood marked by bullying.
“The support of my family and teachers made all the difference,” he says. “My fourth grade teacher, Loretta Williams, really believed in me. In seventh grade, Sandra Spadaccino told me, ‘You’re special, Billy. You just do you.’”
An introverted student, Conroy immersed himself in Greek and Roman mythology and spent time tutoring his younger brother and visiting his mother’s classroom. Though he once imagined a future as a painter or scenic designer, he initially pursued political science and Spanish at the University of Connecticut, with dreams of becoming a translator for the United Nations or the State Department.
“I can’t say why,” he reflects, “but after a while, teaching made more sense, and I switched to the School of Education.”
After graduating, Conroy began teaching third and fourth grades at Batchelder School, where he honed his craft in a supportive, family-like environment. He later taught at Capital Preparatory Magnet School before transferring to Bulkeley High School, where he found his passion working with multilingual learners in the New Arrival Program.
“There, I really found my purpose,” he says. “I even kept a map in my office and placed a star for every country my students came from—Southeast Asia, Africa, Latin America, Europe. I still have that map.”
His commitment to growth led him to a weeklong Harvard University workshop on continuous improvement through the Data Wise framework. Soon after, he was recruited to McDonough Middle School to establish a newcomers center.
“That’s when I fell in love with middle school,” Conroy says. “People warn you about middle school students, but what’s often called ‘disrespect’ is really a form of communication. When you learn to understand it, you can help students in meaningful ways—it’s like breaking a code.”
He credits colleague Zoraida Soler, an ESOL teacher, as a key influence on his approach to both teaching and relationships. In 2017, Conroy was nominated by his peers for Hartford Teacher of the Year, largely due to the success of the newcomers center.
Eager to expand his impact, Conroy earned a master’s degree in educational leadership and became an assistant principal—returning to McDonough just as the COVID-19 pandemic reshaped education.
“I joke that I want to write a book called How to Fall Off a Cliff to describe that time,” he says.
During this period, he worked with his team to strengthen school culture, emphasizing respect, restorative practices and Positive Behavioral Interventions and Supports (PBIS). For Conroy, this work is deeply personal.
“Because of my own experiences, I’m very present,” he says. “I’m in classrooms multiple times a day, paying attention to students as individuals and looking for signs that something may be wrong.”
He adds, “We’re very intentional about addressing bullying. One key is making sure every student has a connection to a caring adult. That’s what helped me. We’re only as safe as our least safe student.”
Conroy credits his principal, Marjorie Rice, as a mentor who has helped shape his leadership. He hopes to one day become a principal and continue advancing multilingual education at a broader level.
Beyond his school, Conroy is an active member of the Hartford Principals’ and Supervisors’ Association, AFSA Local 22, and supports community partners, including Catholic Charities and Integrated Refugee and Immigration Services.
Outside of work, he enjoys yoga, fitness, painting and studying Greek. He and his husband, John Longo, share a love of travel and have recently visited Spain and Portugal, with plans to explore Italy and France in the future.
No matter the topic, Conroy’s focus always returns to his school community.
“I’m very proud of McDonough,” he says. “As part of the Commissioner’s Network, we’ve sustained meaningful change over four years. Our chronic absenteeism rate has dropped significantly, and in the Next Generation Accountability Report, we’ve shown growth across all areas. We’re proud—but we’re not done yet.”
