The purpose of this study was to examine gender dynamics in educational leadership doctoral cohorts and explore the propensity for educational leadership programs to unintentionally perpetuate inequity through continued silence and unawareness of issues related to gender. The study includes narratives from two women cohort members and two professors (one man, one woman), detailing their experiences in an educational leadership preparation program at the pseudonymous Southern University. The authors conclude that it is important for students and faculty to proactively engage gender inequity in both professional venues and during informal interactions. Professors who engage in these conversations create opportunities for students to facilitate discussions regarding gender inequity in educational leadership. The cohort model allows students to be in a supportive environment where difficult conversations can take place, but it can also perpetuate inequity and oppression unless gender dynamics are interrogated and dismantled.