Given the importance of understanding how gender bias impacts the advancement of women into upper leadership, this second-order meta-analysis attempts to explore and summarize previous developments in the gender and leadership literature in order to present the current state of the literature and identify a roadmap for future research. This dissertation delivers three primary theoretical contributions. First, I conducted a systematic review of the leadership and gender literature to create a primer, with relevant definitions and theoretical frameworks, for gender and leadership theory. This review highlighted that little theoretical integration exists to synthesize the literature on gender and leadership. Second, I present a second-order meta-analysis and subsequent relative weights analysis to demonstrate the relationship between personality, gender and follower evaluation of leadership constructs such as leader emergence and other leader behaviors (ex: transformational leadership, ethical leadership, etc.). The final meta-analytic correlation matrix included 89 meta-analytic estimates (total k=1,404; total n=366,329). Results indicate that variation in the evaluation of leaders can be explained by gender, however, the subsequent relative weights analysis indicates that for no construct is gender the dominant predictor. Finally, this dissertation presents a research agenda based on the current findings that will advance the field, including research questions ranging from resolving methodological issues related to the measurement of evaluations of behaviors rather than actual behaviors, to further understanding further moderators of the relationship between gender and leader evaluations.