Women in male-dominated sectors face significant challenges to progress their leadership aspirations. While organizations have activated policies and practices that ostensibly assist women to progress, they still face entrenched gendered practices and cultures that create ongoing obstacles. In this paper, we examine the gendered social practices from insights of 15 women leaders in Australia as they attempt to advance their careers. In particular, on formal policies, informal practices, narratives and social interactions, and informal patterns of unconscious bias and merit, they negotiate in three male-dominated sectors: Trades, Sport, and Surgery. The findings indicate a disconnect between policies and their application. Women were conflicted about the importance of quotas, and often felt unable to access flexible work arrangements upon returning to work after parental leave. Career pathways were often unclear, and women felt a lack of support from their organization, particularly when they attempted to navigate dominant masculine cultures. Drawing on these findings, we argue that executive leaders are central to changing the systemic sexism and discrimination in organizations that persist in male-dominated sectors. To create organizational changes necessary for women to step into leadership roles, we propose four target areas: create accessible and visible career pathways, provide networking support, activate mentoring opportunities, and address unconscious bias.