Recent literature shows an increased interest in generational differences among the workforce, particularly in Western societies. This has coincided with a focus on the role of women as successful leaders in the workplace. Despite this, the exploration and understanding of generational differences amongst female leaders in organisations has received limited attention, particularly in the South African context. The main purpose of the study was therefore to explore whether generational differences among women have an influence on how they approach leadership roles in a South African context. The study also sought to examine whether there are differences in gender identity across the generations as a result of socialisation. The study adopted a qualitative, life histories methodological approach to address the research purposes. Semi structured interviews were conducted with nine South African women in leadership positions from both the Baby Boomer and Generation X generational cohorts. The two generational cohorts were selected as they make up the majority of the current workforce while also being more likely, due to their age, of occupying leadership positions. The interviews were recorded and transcribed, and were imported into Atlas.ti for data analysis. The findings indicated that mothers played a dominant role in the socialisation of women, while fathers were significantly less present in the women’s stories. In terms of the effect of socialisation on career and leadership expectations, Baby Boomers were taught that they should be ‘stay-at-home-mothers’ and after having raised their children could then begin their careers. Generation X believed that they could be career women just as easily as ‘stay-at-home-mothers’. Despite both generations favouring a transformational approach to leadership, each generation differed in the way it practiced leadership. Baby Boomers led in a shared, structured and empowering manner, whereas Generation Xs focused on being attentive, unlocking potential, identifying talents of followers, and assisting in the growth and development of followers within their leadership approach.