The paper focuses on the South African Higher Education environment, engaging with men in leadership and their views on areas that have been identified as challenging in women's lived experiences and the advancement of women towards leadership. Men still dominate positions of leadership and as such, hold positional power and influence in transformation towards a more equitable and diverse leadership profile. Research in this area focuses predominantly on the voices of women, yet there is recognition that men should also exercise agency in this regard. Set within a framework of social justice, critical and social realism, the research considers whether men understand women's lived experiences and challenges of institutional culture, often described in gendered terms. It considers their perceptions of women as leaders, inclusive of their notions of leadership. It is an attempt to grapple with women's perpetual challenges in the Higher Education milieu and the globally persistent underlying barriers to women's advancement. A qualitative approach was adopted and six men in leadership positions were interviewed. Responses to open-ended questions, based on areas highlighted in the literature, were analysed using critical discourse analysis. The findings revealed that though men in leadership appeared to understand the challenges experienced by women, the deeper embedded (real) levels of patriarchy and institutional culture and the impact on women's lived experiences were not fully appreciated. The paper concludes that men's advocacy and agency, though not conclusively so, can be major game-changers in institutional culture and patriarchal practices. The appearance of a perpetual cycle of cultural and structural barriers, and a predominance of research on women's experiences of this cycle, led the researcher to engage with men in leadership to ascertain whether they recognise and comprehend this cycle and whether they exercise agency and advocacy in challenging the status quo.