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, as opposed to hiring from within, contributes to the complexity of filling superintendent vacancies The limited research available on this issue is amplified due to the concern around the shortage of highly qualified superintendent candidates available to fill those top roles (Grissom & Andersen, 2012; Grissom & Mitani, 2016; Kamrath & Brunner, 2014). The role of district superintendent can be cumbersome, yet, 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 they related 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. Limiting the pool of qualified applicants, and contributing to gender-bias in candidate selection were challenges shared by the participants while the building of a culture of leadership and shortening the learning curve were identified as advantages of a GYO hiring approach.