Concerns about a strong positive correlation between leadership and student success (Wood et al., 2013) coupled with community input around hiring from outside an organization, or hiring from within and selecting existing employees to fill superintendent vacancies contribute to the complexity of the hiring process. The limited research available on this issue has highlighted the concern of the shortage of highly qualified superintendent candidates available to fill vacancies (Grissom & Andersen, 2012; Grissom & Mitani, 2016; Kamrath & Brunner, 2014). The role of district superintendent can be cumbersome, yet with the optimal personnel, it can be a role worth pursuing. The information gathered for this ethnographic study was derived from the responses from various stakeholders' opinions, feelings, and experiences as it relates to the superintendent position and 'grow your own' hiring practices in rural districts. Fink and Brayman (2006) make note that the recruitment and selection of administrative candidates have become a national dilemma for the educational domain. It is crucial to attract and employ high-quality applicants when hiring for this essential district role. The information gathered for this ethnographic study was derived from the responses from various stakeholder's stakeholders' opinions, perceptions, and experiences as it relates to the superintendent position and 'grow your own' hiring practices in rural districts. This study revealed there are both advantages and disadvantages to implementing the GYO approach. While implications include limiting the pool of qualified applicants, and contributing to a gender-bias impression on the pool of potential candidates, the building of a culture of leadership and shortening the learning curve are identified as advantages of a GYO hiring approach. This study is significant to the educational community for educators seeking to advance their careers into leadership positions. The study is also significant to school district leadership teams when assessing internal and external strategies to consider in order to find the best candidate to fill an administrative vacancy. [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.]