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The importance of school leaders to student learning has become increasingly evident, as has the influence of leadership preparation programs on the effectiveness of those leaders. Eight participants (novice leaders) from three different non-university-based programs were interviewed multiple times over two to three years about their experiences and challenges moving from leadership preparation into leadership roles. The ways in which leadership preparation, prior experiences, and context shaped their practice was specifically investigated. Cross-case analysis of the leaders’ case studies revealed key themes discussed in the paper, including the degree to which high-intensity programs prepared new leaders for challenging situations, common leadership challenges, and the nature of the positions in which leaders were placed.