ABSTRACT
This research uses a postcolonial feminist perspective to examine how Filipino women leaders turn challenging situations, often referred to as glass cliffs, into opportunities for personal and professional development. Based on unique cultural stories of Filipino women leaders from different sectors, we present three theoretical mechanisms: cultural capital conversion, cultural ambidexterity, and cultural resilience. These concepts are illustrated through cultural archetypes, the hero, the matriarch, and the responsible older sister, which show how influences from pre-colonial matriarchs and Filipino values such as bayanihan, pakikisama, and utang na loob influence leadership experiences. We extend the glass cliff phenomenon by showing how colonial histories and cultural values alter its expression in postcolonial settings. This study contributes to decolonizing leadership research by showcasing how cultural values form unique paths for women’s leadership success, questioning the universal relevance of Western theories, and promoting more inclusive theoretical frameworks in organizational leadership.