This case study examines secondary school leaders' perceptions of their ability to build positive relationships with the adolescents in their care as a means for improving students' academic performance. A sample of administrator participants was chosen from four suburban high schools with similar demographics located in the South Central Pennsylvania region. Participants were surveyed, interviewed, and observed in an effort to identify whether or not their self-perceptions of how they build positive relationships with students and their actual behaviors align. A comparison between leadership styles and the gender of the participants was also made to determine whether or not gender influences the behaviors of school leaders as it explores the use of justice-oriented and care-oriented approaches to school leadership. This study is grounded in a theoretical framework based on the works of Shapiro and Stefkovich (2011), Noddings (2005), Kohlberg (1975), Gilligan (1982), and Tannen (2001) as it investigates how secondary school administrators use transformational, ethical, and authoritative behaviors in their daily interactions with students. Using four case studies and the results of an electronic survey, this study examines whether or not school leaders' perceptions of their success in building relationships with students are accurate. The findings of this case study illustrate that transformational and care-oriented styles of school leadership are the most effective in building positive relationships with secondary students. Additionally, there were no significant differences between the survey or interview responses of male and female participants, demonstrating that in this particular study, the gender of the participant did not increase the likelihood of transformational or care-oriented behaviors being used. This study asserts that all school leaders can be more effective in meeting the demands of accountability while still caring for the well-being of students' social, emotional, and cognitive growth by prioritizing the building of relationships over accountability itself, and by developing their own overall capacity to balance both transactional and transformational responsibilities. This research contributes to existing literature on ethical educational leadership, gender-related styles of communication and leadership, and secondary school leadership. [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.]