<p> The Female-To-Male (FTM) transgender community has begun to receive a lot of attention in recent years. Academic research executed with a focus on the experiences of the FTM community is also growing quickly and exploring issues and concepts beyond transition. The effect of social expectations on the leadership experiences of FTM leaders has yet to be examined, specifically the influence of the social expectations of masculinity and leadership on FTM leaders. This dissertation seeks to capture the experiences of 4 transgender men who hold, or have held, leadership roles in their organizations of employ and to inquire about how the social expectations about what it means to be a man, or how to appropriately behave to be perceived as a man, affects themselves as leaders as well as their leadership experiences. The work also elucidates a relationship between socially-imposed stereotypes on gender identity development as well as the importance of gender identity gaining recognition as a workplace well-being issue.</p>