This qualitative case study of six principals and their district-level supervisors examines how principals' self-efficacy is influenced by the feedback they receive from their supervisor, as well as the ways the experience and influence of this feedback varies by the principals' gender. The messages conveyed to principals about entering formal leadership early in their careers were starkly different according to principals' gender, and these messages influenced the principals' persistence and self-efficacy. Specifically, rising male principals received messages of support and encouragement to expectantly fulfill the role of principal. Conversely, rising female principals received mixed messages encouraging them to pursue leadership credentials rather than principal positions. Females were faced with messages aimed at conjuring feelings of guilt for advancing, and navigated barriers to entering the formal leadership rank. Additionally, although female and male participants initially framed effective leadership similarly, the feedback they felt they received regarding their skills, their conceptualizations of themselves as leaders, and their access to employment were sharply divided based on gender, with men favored in both categories. This difference had real implications for how women viewed their leadership capabilities and potential success as school leaders. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]