Despite the dramatically increased entry of women into general surgery and surgical subspecialties, traditionally male-dominated fields, there remains a gross under-representation of women in the leadership positions of these departments. Women begin their careers with fewer academic resources and tend to progress through the ranks slower than men. Female surgeons also receive significantly lower salaries than their male counterparts and are more vulnerable to discrimination, both obvious and covert. Although some argue that female surgeons tend to choose their families over careers, studies have actually shown that women are as eager as men to assume leadership positions, are equally qualified for these positions as men, and are as good as men at leadership tasks.Three major constraints contribute to the glass-ceiling phenomenon: traditional gender roles, manifestations of sexism in the medical environment, and lack of effective mentors. Gender roles contribute to unconscious assumptions that have little to do with actual knowledge and abilities of an individuals and they negatively influence decision-making when it comes to promotions. Sexism has many forms, from subtle to explicit forms, and some studies show that far more women report being discriminately against than do men. There is a lack of same-sex mentors and role models for women in academic surgery, thereby isolating female academicians further. This review summarizes the manifestation of the glass-ceiling phenomenon, identifies some causes of these inequalities, and proposes different strategies for continuing the advancement of women in academic surgery and to shatter the glass ceiling.