This study examined supervisory strategies for employees with criminal history from the perspective of supervisors with experience in overseeing formerly incarcerated employees. The primary goal of the study was to determine strategies used by supervisors that can be integrated into management training and disseminated to employers interested in hiring individuals with criminal history. For that purpose, 10 semistructured interviews were conducted with supervisors at Pioneer Human Services (Washington State, USA), a large nonprofit social enterprise that operates businesses employing justice involved individuals and reinvesting revenues into services that support this population. The purposive sample of supervisors consisted of individuals considered to be skilled in supervising employees with criminal history. Data were analyzed using a priori and inductive codes. Two supervisory strategies emerged from the interviews: supervisors should demonstrate cultural competence in their interactions with formerly incarcerated employees, and be knowledgeable about community resources to connect employees to resources.