In Kentucky, over 100 school principals are replaced yearly. In many cases assistant principals will be the replacement principals, but they must have the leadership experience and skills necessary to prepare them for the principalship. This descriptive action research gathered principals' recollections about their own preparedness levels in the roles and responsibilities of the principalship. Additionally, the project was designed to gain information about experiences and training practices that helped or hindered transition. Participants were current practicing principals from one cooperative region in Kentucky. All participants completed a survey, and two were chosen for follow-up interviews. Data from the study were compiled and analyzed using open coding and Chi-Square. From this research, recommendations for preparing assistant principals were fashioned, which include training supported by local district personnel and strategies to be implemented by principals around communication, mentoring, and experiences. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]