Women are beginning to vie for and attain executive positions around the world more frequently. Currently, 24 countries in the world have a woman president or prime minister (UN Women). Historically, more than 70 countries worldwide have had a woman executive. However, most countries, around 65%, have never had a woman executive, including prominent and powerful countries such as The United States and Russia (Britannica). In this research, I aim to answer the question: given the historical absence of women in executive positions and the recent numerical increase of women executives, what social and political factors enable women to rise to the highest level of government? In this regard, I use the regional case of Central and Eastern Europe (CEE). Noting that most of the 19 countries that I survey in CEE (13 of 19) have had a woman executive, I analyze the paths to political power of several women leaders in the region, including Ana Brnabic of Serbia and Zuzana Caputova of Slovakia. I also analyze the cases where there have been no women executives, such as Montenegro and Albania to provide women not attaining executive power. In terms of organization, this research first puts forth a global picture of women executives, noting the disparities in terms of countries and regions. Subsequently, the paper highlights the countries of Central and Eastern Europe, using case studies as example of divergent paths to power by women executives and cases where there have never been women at the executive level.