This study investigated the structured mentoring program provided to novice superintendents by the SSA (School Superintendents of Alabama). This study examined new African American superintendents' perceptions of the facilitating factors and barriers that influenced the success of the program and the benefits in terms of attaining district goals and their own career goals, personal growth and development. A qualitative research approach was implemented as the method of inquiry for this study. Purposeful sampling was used to provide an in-depth knowledge of the structured mentoring program. Data sources included archived superintendent surveys and superintendent interviews. This study sought to provide significant information to the body of work related to mentoring programs for new superintendents from the lived experiences of those involved in the program. Mentoring has been proven to be an effective way to support new leaders in many other disciplines. However, the perceived effectiveness of structured mentoring programs has not been studied in depth. The impact and benefits of mentoring on underrepresented and minority school superintendents remains limited.The findings of this research indicated that the SSA structured mentoring program appears to be beneficial for new African American superintendents. Participants indicated that they have seen positive changes in the development of their leadership skills, better understand their roles and available resources and that they are more equipped to handle the demands of the position. This study verifies the importance of providing a mentoring program for new school administrators. There are areas that need further development, but the program appears to support the clear majority of the needs identified by new administrators. The findings also identified program components that needed strengthening which were additional training, transitions/next steps and the selection and mentor matching qualities. The components and elements identified in this research are closely related to the elements used in the conceptual model by Zachary (2009), which served as the conceptual framework for this study. This study fills a gap in the literature and presents new information that should be of value to practitioners and researchers interested in processes focused upon the effective development and growth of new administrative leaders. Although the findings cannot be generalized to other settings, it is hoped that this study will be helpful in creating exemplary mentoring programs for all new superintendents. [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.]