What enables women to take on leadership roles? What inhibits them? What are the gains when women take on leadership roles? Is leadership gendered in the Philippines? These are some of the questions that were asked to unravel the leadership experiences of Filipino women. The Philippine statistics showed obvious gaps in women's leadership in the country. However, their significant contribution to community development and nation-building could not remain hidden and muted. Two cases were selected to unravel the narratives of leadership experience of women. One case was focused on women leaders in agriculture, specifically in farm production, and the other was focused on women leaders in a national peace negotiation towards ending a protracted armed conflict in Southern Philippines. Using qualitative methods and a social constructivist lens, this paper connected the emergent patterns of how the Filipino women leaders navigated leadership in a stereotypically male-dominated arena of agriculture sector and peace negotiations. Results showed that gender bias stood out as a common inhibitor to women's leadership. Nonetheless, like any barrier faced by women in life, gender bias was confronted, addressed, and tamed. In both cases, the women were able to successfully overcome well-entrenched gender bias in navigating their leadership experience by maximizing existing structural mechanisms, optimizing strategic support, galvanizing social engagement, and allowing themselves to be driven by a purpose for the greater good. Findings offered insights into some practical implications on strengthening women's leadership in complex realities.