Superintendents are leaving districts at an alarming rate across the nation, which can lead to detrimental effects for students, staff, and communities. Where once this was a position of prestige, it has become one in which educational experts are choosing to leave districts because of the various stressors that comprise their jobs. It is not known how or why superintendent tenure is influenced by school board relationships, politics, retirement/career advancement, school culture, or student achievement in Montana. The purpose of this qualitative phenomenographic study was to gather information on the perceptions and experiences of superintendents across Montana as they related to both the dissatisfaction theory and the push-pull theory. Fifteen superintendents were interviewed using semi-structured interviews. The analyzed data revealed that school culture was the greatest precipitating factor in determining whether or not a superintendent would end their tenure with a district. School board relationships with the superintendent were seen by many superintendents as part of creating either a positive or negative culture and also played a significant role in whether or not a superintendent wished to remain in a district. Potential implications of the results indicate that superintendents will not remain in a district long-term if their relationship with their school board is poor, and they are unable to enact a positive school culture. Future qualitative research exploring which aspects of school culture are the greatest triggers causing superintendents to leave districts is recommended. It is also recommended that there is further research exploring ways in which to strengthen the superintendent and school board relationship. It is strongly advised that school boards work to build positive working relationships with their superintendent if they wish to keep them in the district. [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.]