This research explored the influences that sexual orientation and gender norm adherence play in impacting perceptions of a leader’s hirability into and evaluation within a leadership role. Though sexual minority issues in the workplace represent a growing field of research, investigations into sexual orientation’s impact on outcomes relevant to leadership remain scant. As increasing numbers of openly gay and lesbian men and women take positions of leadership, there is a need for more information regarding the experiences of sexual minority leaders, with potential benefits to these individuals, their organizations, and related stakeholders. The research conducted here was intended to address this gap by investigating the effect of a leader’s sexual orientation and adherence to gender role behavioral norms on perceptions of their leadership in both stereotypically masculine and feminine leadership roles. Participants were asked to review and evaluate the qualifications of a male or a female candidate of heterosexual or gay/lesbian sexual orientation for a managerial position in retail sales. This position was described in particularly masculine/agentic or feminine/communal terms. They then viewed the candidate’s interview video, with the applicant displaying either an agentic or a communal behavioral style, and subsequently provided an evaluation of his or her effectiveness as a leader. Drawing from both role congruity theory and sexual orientation research, it was hypothesized that discrimination will occur based on the distances between stereotypes of gay men and lesbian women (specifically, that gay men are feminine and lesbian women are masculine), gender role expectations of men and women, and beliefs about a leader role’s requirements. It was expected that gay men would be perceived as less hirable into a leadership position than heterosexual men, and even more so for positions with masculine-typed tasks, while lesbian women would be perceived as more hirable into a masculine-typed leadership position than heterosexual women. It was further expected that, when a male leader uses an agentic (masculine) style, they would be perceived as more effective if they are heterosexual than if they are gay. On the other hand, lesbian women who enact agentic behaviors would be evaluated as less effective than heterosexual agentic women. However, the masculine stereotype of lesbian women was predicted to null the effects of prejudice demonstrated in evaluations of communal female leaders’ effectiveness, so that lesbian women who enacted a communal (feminine) style were expected to receive more positive evaluations of leader effectiveness than heterosexual communal women. Although findings did not support hypotheses, several significant interactions were revealed in unexpected directions. Sexual orientation had no influence on men or women’s hirability into leader roles, regardless of the requirements, and no impact on ratings of female leader’s effectiveness. Similarly, both gay and heterosexual men received similar ratings of effectiveness when employing a communal style; however, while this rating did not change when gay men instead used an agentic style, ratings for heterosexual men were significantly lower. Implications are discussed in light of recent cultural shifts around beliefs about and attitudes toward LGBT individuals