Eighty percent of Colorado's students attend schools in rural or small rural school districts, but the majority of those students consistently perform below or well-below expectations on the state performance assessment (PSAT). In order to hold staff and stakeholders accountable for implementing successful strategies that lead to systemic changes, the principals are tasked with developing systems that use student achievement data as the metric to assess the effectiveness of the changes put in place. This research aimed to provide educators with a better understanding of the specific organizational leadership characteristics that lead to the development and implementation of enabling structures within rural high schools by examining the effects of enabling school structures and academic optimism on student achievement scores in rural high schools through principal- and teacher-reported data. The theory of academic optimism, which combines three school-based elements and has been shown to influence student success outcomes even when controlling for socioeconomic status, served as the conceptual framework for this study. Collective efficacy, the emphasis placed on academics in a given school, and faculty confidence in parents are some of these constructs. The study was framed by the theory of enabling school structures as an organizational leadership model in addition to the theory of academic optimism. In this study, school administrators' views on enabling school structures and academic optimism were compared to student achievement data and outcomes for rural high school students in Colorado. Although the study's findings did not corroborate the aforementioned theories, they did demonstrate that enabling school structures can produce beneficial effects in institutions serving students from lower socioeconomic backgrounds. [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.]