Results: This chapter analyzed the leadership styles of female and male leaders in HEI management teams in Australia and Portugal. It found that both women and men in Australian universities valued transformational leadership skills, whereas the male respondents in Portugal saw traditional management as more effective, even though female respondents considered women demonstrated transformational leadership. It also found that while women's leadership is recognized in Australian universities, in Portugal men saw women's leadership as problematic. Originality/value of chapter: The findings suggest that there is more possibility for transformation in the academy if both men and women in HEI leadership value women's leadership role. Methodology: A total of 44 interviews with female and male university senior managers in Australia and Portugal were conducted by the authors and then analyzed using thematic content analysis. Purpose: This chapter examines if women in Higher Education Institutions (HEIs) are constrained in their leadership style and if the organizational culture makes them less valued in senior management teams. It then explores if the 7-S organizational framework has relevance to gender and leadership in HEIs. The nature of authority within HEIs increases the complexity of leadership within an academic context. Leadership is often vested in a single person, and the positional power of Rectors/Vice-Chancellors (VCs) is based on authority, discipline knowledge, experience, and peer and professional recognition. The literature highlights that HEIs continue to be male dominated and that women are underrepresented in university leadership.