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Turnover is a serious problem facing the American public school superintendency. This paper reports the findings from a qualitative study, which examined how novice superintendents described the support and mentoring experiences they received throughout their careers. The study revealed that the supports superintendents receive throughout their career trajectories are iterative, with both topics and sources of support changing throughout their initial interest in, training for, aspiration to, and eventual achievement of a superintendent position. Clear themes emerged throughout the phase of superintendents’ career trajectories. Additionally, a delineation between technical and social-emotional support emerged.