Community College Men of Color Initiatives (CCMCIs) are increasingly popular strategies utilized to promote retention and completion among Men of Color (MOC). CCMCI directors offer a unique positionality in understanding how their identities, institutional contexts, and power dynamics affect their design of programs and participating students. Using a critical phenomenological approach, the authors of this study explore the lived experiences of CCMCI directors in conceptualizing, implementing, and assessing these initiatives.