The public school superintendent has been studied since the early 1800s. Throughout history, the role of the superintendent has evolved into an increasingly challenging role. Between 1860 and 1960, school boards categorically selected superintendents who met a predetermined set of characteristics. White middle-aged males dominated the field. During the 1960s and 1970s, superintendents sought advanced degrees and preparation programs. Mentorships became integral components of the preparation programs that were designed to prepare prospective superintendents to meet the increasing demands of the job. During recent history, superintendents have been plagued by a multitude of academic, societal, and political challenges that are threatening the position of the school superintendent. Increased turnover rate and a declining interest in the field, compounded with the issues of financial management, staff recruitment, instructional leadership, communication, school governance, and strategic planning, are affecting the organizational stability of school districts. Upon entry, the superintendent must balance decision-making responsibilities with leadership strategies regarding the multidimensional functions of the school district. The literature is rich with studies regarding these compounded challenges within the organization of the school district, and research demonstrates that superintendent longevity is linked to organizational sustainability. However, the research literature lacks qualitative research studies focusing on superintendent entry plans, associated superintendent sustainability, and organizational stability. / text