To investigate the relationships among evaluator attitudes, the role congruity biases many people consciously and unconsciously maintain, evaluation practices, perceptions of leader efficacy and success, and leader persistence in two community college settings, a mixed-methods study was conducted. Leaders are the products of their experiences, environments, the greater society within which they live, their personal attitudes and biases, and the attitudes and role biases of others. Over time, a corpus of multi- disciplinary research into the complex web of societal, professional-organizational, and institutional attitudes, expectations, and behaviors that impact career choice decisions and career advancement opportunities for leaders, and how leaders are evaluated, has waxed and waned. A review of theoretical literature and past research relevant for application in the community college context is provided. Literature exploring four distinct research areas was analyzed, with emphasis on the latter three : (1) leadership style; (2) the functions attitudes and attributions play in leader evaluations; (3) the relevance of role congruity expectations on evaluations of leaders; and (4) the variables directly influencing leader performance evaluation process outcomes. In the past several decades, women have gained increased access to middle management and some supervisory positions, yet they remain a relative rarity in positions of elite leadership and as chief executives. A role congruity bias explanation for this phenomenon in the community college setting was examined. The study employed the use of both quantitative and qualitative methods to examine questions regarding the functions of evaluator attitudes, attributions, and role congruity expectations in leader performance evaluation processes. The study consisted of an embedded two-case- study comparison, conducted in two phases. The results of this study support the assertion that gender-role attitudes, as explained by a role congruity theory of prejudice toward female leaders, negatively impact the professional advancement aspirations, opportunities, and persistence rates of female community college leaders