The changing ways in which organizations serve society combined with the rapidly changing demographics of the people that these organizations are comprised of requires us to reexamine what we need from our leaders. While transformational leadership has received a lot of attention in organizational leadership research and organizations have placed increased attention on shifting their leaders’ styles to being more transformational, not enough effort has been made to understand how to develop transformational leaders from traditionally marginalized communities. Despite historically and continually being natural leaders in their communities and society at large, women, and women of color in particular, remain an untapped transformational leadership resource in organizations. This dissertation examined the existing research on the style and effects of transformational leadership and leaders, the relationship between race, gender, organizations, and leadership, and the stereotypes and perceptions that women in leadership positions face. The research methodology was a three-phase process, utilizing Grounded Theory to inform each subsequent phase, and included an observation phase of all participants in a setting showcasing their leadership function, an interview phase with one participant from each site, and a focus group phase that grouped the women together by their job site. Participants consisted of 7 women from two different sites with at least 15 years of work experience, including at least two years in formal leadership roles. This research has a wide range of future implications, including illuminating the ways in which successful female leaders leverage emotional labor in their leadership roles to engage transformational leadership qualities, and highlighting opportunities to foster these traits in other future leaders. This research identified various implications for researchers, multiple social institutions and organizations, leaders, faculty members, and practitioners to positively impact women leaders’ entry into and advancement through leadership positions.