Women represent only 15% of the executive level leadership in the United States and only 2.4% of the chief executives positions. Research into the factors that empower and propel some women leaders and not others into executive management is seriously lacking. The current study was conducted to investigate the drivers and restrainers of female progression in the workplace and the influence they have on career progression. The study was also conducted to research and investigate the surrounding factors that would qualify a woman for consideration for an executive management position and to capture the perceptions of the executives, their backgrounds, and other characteristics pertinent to their leadership role. A qualitative phenomenological method was used, and 21 executive level leaders, women and men, participated in the study. Leaders from education, government, services, and non-profit organizations were interviewed in the City of Phoenix Arizona. The resulting data were analyzed across the genders to measure any similarities or differences that may have existed. The results of the study support that gender stereotyping and bias are still playing a prominent role in the progression of females in the workplace and their advancement to the executive leadership positions within an organization.