A persistent marker of women’s political inequality is the gender gap in heads of state, so how do women break this glass ceiling? Women’s Paths to Power asks two questions of interest to anyone studying the gender politics of executive office: (1) under what conditions are women likely to be appointed or elected president or prime minister and (2) what pathways do women take in their successful pursuit of these offices? Evren Wiltse and Lisa Hager construct a new data set for their multimethods approach to analyze three main pathways—family, activism, and political career—by which women have successfully pursued executive office. The book is a useful comparative study that adds important depth to understanding the dynamics of gender and executive political office. The book unites two strands of literature: the pathways women use to achieve executive office and the institutional/political features that support women’s ascension to executive office. This unity allows the authors to present novel conclusions regarding the relationship between the personal and the institutional. The first half of the book uses qualitative analysis to build theoretical expectations explaining when women pursue familial, activist, or political careerist paths to executive office, joining historical analysis of 1960–2020 with descriptive statistics. The second half of the book uses global data from 1990 to 2015 to examine political and institutional dynamics, the impact of previous women leaders, and the “longevity puzzle” in relation to these three pathways, concluding that the path women take to office and particular institutional dynamics matter in explaining how women come to power. Perhaps most striking is that their results provide only mixed support for previous research. Wiltse and Hager claim that their more comprehensive data set provides more nuance that may erode earlier claims about the importance of region for whether and how women achieve executive office. At the same time, they provide more nuance in considering the importance of institutional features, like appointment or election, and broad importance of political careerist paths to office. Most novel is the pathbreaking question explaining how long women serve in executive positions. They find that women executives in the Global North and those in presidential systems tend to serve longer terms. These scant results suggest the importance of ongoing research for understanding executive longevity.