This qualitative case study examined the research exploring how female teachers had perceived their potential challenges in becoming a principal, and how those perceptions actually changed as they made the move from the classroom to the principal's office. The purpose of the study is to investigate how female administrative candidates assessed and better prepared themselves for future work environments. The study is based on data collected from two interviews, one with a superintendent from a traditional school and the other from an online principal. The results of the study indicate that the school administrators had developed an administrative plan that helped them facilitate better transitions from the classroom to the principal's office. [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.]