The following qualitative study examines a social learning initiative to support the leadership development of women in sport. Specifically, a Community of Practice (CoP) of femininity was cultivated to inspire women (and male allies) to develop their leadership capacities in the androcentric field of sport. Data were generated from 12 sport leaders (10 women and two men) over a year and a half to collect their experiences of participating in this initiative. Data collection included interviews, observations, surveys, and informal discussions and were analyzed using thematic analysis. The themes discussed include: supports to develop confidence, improved leadership skills, self-awareness of leadership capacity and influence, increased leadership opportunities, men supporting women in leadership development, and the value of social learning. The authors hope these findings will inspire others to implement similar initiatives to fields where masculinity is dominant. This may allow other CoPs of femininity to emerge to support women in their leadership development.