Through a basic qualitative approach this study examined the leadership styles of superintendents to determine if the styles of leadership have a positive, negative or no impact on student achievement. The perceptions and practices of the leadership styles of traditional pathway and alternative (non-traditional) pathway of superintendents is also examined as it relates to their ability to impact school district effectiveness. In the past, studies have only examined the characteristics of non-traditional superintendents from among the largest school districts in the country (Council of the Great City Schools, 2019). This study focused on the similarities in the leadership styles of traditional pathways and alternative pathways of superintendents was warranted, because as the school districts follow the vision, mission, and direction of those superintendents it is incumbent upon the district as a whole to meet their state outcomes requirements. The job of a school superintendent is demanding and challenging, the national average for a superintendent is five to six years in accordance with the American Association of School Administrators (AASA, 2020). Results from this study indicate the need for a robust and ongoing professional development after the completion of a leadership preparation program for the non-traditional (alternative) as well as traditional superintendents. The results lead to specific recommendations related to executive coaching, action research to study if use of personal data, tracking of new initiatives/interventions, or implementation of holistic and real-world experience impact on the competence of academic achievement or state student outcomes. [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.]