While more women than ever now participate in the paid workforce, it still can be hard to find women in top leadership positions. To understand why so few women are in top leadership positions, particularly in the Asia-Pacific region, the Center for Creative Leadership (CCL) set out to understand what factors help women achieve leadership positions, what factors prevent it, and how organizations could add more women to their leadership ranks. In this paper, the authors raise five key questions that women should reflect on as they consider their ambitions. They summarize five key lessons that came up repeatedly in conversations with women leaders who had worked their way into leadership positions. The authors also discuss some of the changes organizations can make to increase the number of women leaders. These include policies and changes in organizational culture. Research was conducted two phases. First, the authors surveyed 204 women leaders from Singapore, Australia, India, and Korea. The authors gave them a list of reasons that might contribute to the lack of women in leadership positions and asked them to select up to five items they most agreed with and five they most disagreed with. In phase two, the authors conducted 27 face-to-face interviews with women leaders working in Singapore. Women told their personal leadership stories, shared their perspective on women leaders' career enablers and blockers, and also completed the phase 1 survey. The authors learned that there is no single reason or simple solution. Increasing the number of women in leadership positions will require aspiring women leaders to develop themselves professionally and, in some cases, adopt new behaviors. But the organizational context that women work within is also important.