Elite-level leaders in business and government make significant and far-reaching decisions influencing many facets of society. However, relatively few of these powerful positions are held by women. This article explores gender in leadership by focusing on the difficulties women experience in attaining and being seen as effective in top leadership positions. It begins by revealing the lack of parity between the sexes in leadership and in the remaining sections it addresses empirical research that serves to illuminate the leadership labyrinth, or obstacles to women’s progress, also known as the glass ceiling. In the first section, research on gender and leadership styles, traits, and effectiveness is reviewed followed by a consideration of how both domestic responsibilities and current organizational cultures differentially impact women and men on their journey to top leadership positions. The focus then shifts to examining how stereotypes, prejudice, and discrimination contribute to women’s under-representation in elite leadership roles by both impacting perceptions of and responses to women as well as impacting the experiences of women themselves. The final section concludes with thoughts on promoting parity in top-level leadership.