A growing number of traditional school boards and city mayors are looking for the next generation of school superintendents to come prepared with a variety of professional backgrounds to provide instructional leadership for school districts. The primary purpose of this qualitative study was to examine and describe the experiences, of five urban non-traditional superintendents. Associated research methods, namely interviews with study participants and the identification of major themes emerging from the data, were employed. Six emergent themes were revealed, including change agent, accountability, political connection/clout, school reform, student achievement and excellent leadership. Profiles of the participants were offered to provide a context for the results of this study. In relation to the major themes, these participants believed that their backgrounds in corporate worlds and other professions uniquely prepared them for the increased challenges of today’s school superintendency. They all indicated that they assumed the helms in their respective school systems for altruistic reasons. However, once on the job, the participants noted that they suffered personally and professionally. They found themselves victims of little respect from the community, media and from their own governing bodies. In terms of preparation for the job, the non-traditional superintendents practiced self-study through reading leadership and journal articles and by attending conferences. The participants also experienced different challenges in gaining certification for the superintendency due to disparate state regulations governing licensure. Several recommendations resulted from the findings of this study. Since academic performance is the primary indicator of success or failure in education today, future researchers in this area might consider a quantitative analysis of student achievement in districts led by non-traditional superintendents compared to academic performance in those systems led by their traditional counterparts. In addition, it is suggested that these participants’ views on superintendent preparation and certification and on governance issues may be considered by school districts, state and federal agencies and by universities as they develop future policy and programs. Other recommendations addressed the need to study female non-traditional superintendent governance and non-traditional leaders in smaller school districts as it relates to these issues.