The purpose of this qualitative study is to explore women’s ascension to leadership positions. Two women CEOs were interviewed for this study. The literature on women leadership shows that many women might not be attaining CEO positions because of a lack of mentors, leadership-career aspirations, and experience, gender inequality, and companies’ preference for leadership styles based on masculine characteristics. The literature shows these factors affect women’s ascension to such leadership positions. This study found that women fall under the masculine leadership styles, even though their preferences differ. Furthermore, gender inequality seemed to be tied to age discrimination as well. The article concludes with an examination of nuances concerning gender inequality as it relates to leadership ascension, that is, the minute micro-aggressive messages that might be perceived as part of the culture. Furthermore, the implication that women need more mentors to prepare them for leadership roles is examined. This implication holds further ramifications as leadership approaches play roles in empowering or disempowering women.