The aim of this study was to explore the application of culturally responsive school leadership (CRSL) in an out of school time organization (OST). This was accomplished by analyzing how the actions of leaders both enabled and constrained CRSL. Research was conducted with Inspire Mentoring an OST organization that provides mentoring services to approximately 90-120 high school students of color from freshman through senior year. Approximately 60% of the mentors identify as people of color. The data collected for this qualitative case study occurred over 6 months and included: 6 semi-structured interviews with executive leaders and adult mentors, 5 observations of organizational meetings and community workshops, and reviewed documents from Inspire Mentoring. The leadership practices observed were analyzed using the behaviors of CRSL. This study suggest that positional OST leaders should become more connected to their community understanding longstanding inequities, interrogate their own worldviews, and work in tandem with minoritized youth and community members to address cultural youth development needs.