The school district superintendency is one of the most challenging occupations within public education today and is characterized by high turnover rates (Yates & De Jong, 2018). At times, a public school superintendent experiences difficulties leading to their departure. Examples of such difficulties that require strong leadership skills are dissatisfaction from certain community members, tension with a local school board member, (Grissom & Andersen, 2012), and stress associated with regularly meeting growth and achievement measures set by the state department of education. Additionally, the superintendent is tasked with addressing constantly changing demands of internal and external stakeholders with multiple fiscal limitations (Tekniepe, 2015) while being expected to appropriately handle the demographic changes of the community and district, effectively manage the overall budget, and provide instructional leadership for the internal stakeholders of the district. These demands are difficult to meet when the superintendent does not remain in the position long enough to make substantial changes or is unable to effectively utilize specific leadership traits. This quantitative study set out to determine if a connection existed between tenure and the leadership orientation of Wyoming school superintendents in relation to how they utilize Bolman and Deal's (2017) frames of leadership when facing challenges and experiences associated with the position. The survey results and findings of this study detail the traits and frames of leadership utilized by current Wyoming superintendents when faced with common difficulties faced as a school district leader. [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.]