This study examines gender differences in leadership style and the influence of these differences on perceived leader effectiveness in higher education. Leadership style is defined in gendered terms, which include traditionally agentic styles for men and communal styles for women, and therefore transformational and transactional leadership styles are closely examined. Data were gathered from a two-stage national survey of college presidents and their senior-level leaders, faculty, and administrators from over 200 postsecondary institutions in the United States to analyze these differences in leadership style and leader effectiveness. Multiple block regression analyses demonstrate that gender has a mild correlation with perceived effectiveness, with female presidents being slightly more likely to be perceived as effective leaders. In addition, transformational leadership, which is often connected with communal leadership behaviors, is highly correlated with leader effectiveness. These findings are consistent with the literature in that transformational leaders that exert communal and relational leadership behaviors are usually viewed as more effective leaders than their transactional counterparts that enact agentic behaviors. Finally, institutional context also has a strong relationship with perceived effectiveness for both leaders and subordinates. The research results have implications for transformational leadership training, mentoring, fostering female leadership, and improving institutional context. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]