The purpose of this research was to examine the accomplishments and obstacles of central office administrators who have followed traditional educational career paths with those who have followed non-traditional paths. The demographic markers, educational backgrounds, administrative responsibilities and tasks, and significant positive and negative experiences of five traditional central office administrators (have served three or more years in educational capacities) and five non-traditional central office administrators (have served less than three years in educational capacities) were analyzed. The methodology included a pilot study and individual interviews. Themes, patterns and discrepancies of the data were identified. The experiences of traditional and non-traditional administrators were categorized according to those outlined in the New York State Council of School Superintendents' Model Board of Education Evaluation of a Superintendent. As relationships were noted, further analyses compared and contrasted data within each competency. This study may be of significance to both traditional and non-traditional administrators, who may benefit from identifying particular areas of strength and weakness connected to their respective career paths so that they may be properly prepared for the evaluative process, whether it is formal or informal. [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/en-US/products/dissertations/individuals.shtml.]