This paper attempts to identify paths by which women can break the political glass ceiling of executive power in Asia. In doing so, it aims to answer the following question: Which conditions have been necessary and/or sufficient for women to break the political glass ceiling in Asia since 1998? This paper evaluates existing theories on women’s participation in executive power by applying those theories to Asia through qualitative comparative analysis (QCA). Overall, we find there are three alternative paths: 1) having the support of one of the two main parties in a favourable zeitgeist setting for women’s political participation; 2) having the support of one of the two main parties in liberal regimes where no woman has previously held that executive position; and 3) having both the support of one of the main parties and family ties to a political dynasty in liberal regimes. We also find there are two different configurations that keep women away from office: either lack of support of one of the two main parties in the country or a history of previous female executive leaders in contexts where there is a unfavourable zeitgeist for women’s political participation.