The purpose of this phenomenological study was to explore how novice female principals experienced preparedness upon completing an aspiring leaders program through a regional leadership development organization. This study provided voice to female principals and highlighted their lived experiences. Purposive sampling was utilized to identify nine female principals leading in public schools in the southeast region of the United States. A semi-structured interview protocol was utilized, and interviews were transcribed and open-coded for theme identification. The following themes emerged in this study: leadership story, courageous conversations, mentoring relationships, relevant on-the-job experience, and leading in a pandemic. Further, results from the inquiry suggest avenues for further research and implications for aspiring principals, school districts, higher educational institutions, regional leadership development organizations, and state departments of education. [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.]