Scope and Method of Study: This Naturalistic Inquiry Case Study examines principal succession at two small, rural high schools through naturalistic inquiry presented through the lens of Mary Douglas' grid and group cultural typology. A grid and group cultural analysis survey was sent to all school employees then in-depth, follow-up interviews and observations were conducted in order to gather the personal side of the principal succession process. This method provided a constructivist perspective. Findings and Conclusions: The results of this study are meant to contribute to the body of literature on principal succession. The findings provide insights that are helpful for incoming principals as they traverse through the first year in a new assignment and for central office administration as they place and mentor principals placed in new positions. Findings included the need for the principal to provide credibility, stability, listen and gather input and to earn trust and respect before any cultural changes could be accomplished. [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.]