Since 2016, the Massachusetts Probation Service has worked to increase diversity within its ranks. Pamerson Ifill, who was recently promoted to become the first Black commissioner of probation, leads these efforts. Diversity within the agency has steadily grown under his leadership, resulting in a bigger hiring pool, a diverse workforce, job satisfaction, and successful outcomes for people on probation. We spoke with Commissioner Ifill about how he approached the problem, attracted a diverse pool of candidates, and ensured that they not only grew in their jobs to serve people supervised by probation but also that they achieved personal and professional satisfaction.