The purpose of this study was to examine mentorship and its effect on assistant superintendents' emotional intelligence, challenges, and the desire to become a superintendent. The 149 participants surveyed in this study were assistant superintendents in Nassau and Suffolk Counties in Long Island, New York and Westchester County, New York. An independent sample t-test between assistant superintendents who have a mentor that were superintendents versus assistant superintendents that do not have a mentor was performed, followed by an item by item frequency analysis. The results show that assistant superintendents who have a mentor are more willing to take on the challenge to be a superintendent. An item by item analysis shows that assistant superintendents have 20% more value in the importance of items challenge and social networking.