Current and former CCL researchers (Diane Bergeron, Cathleen Clerkin, and Meena Wilson) argue that gender differences in access to leadership development experiences is a factor in the lack of women in top positions. In this updated chapter, using CCL’s Lessons of Experience (LoE) framework, they review gender differences in five key areas: challenging assignments, developmental relationships, coursework/training, hardships, and personal life experiences. Implications for practice and future research directions are discussed. Although Meena passed away in 2020, her contributions to this chapter remain.