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Identifying the elements of principal preparation program effectiveness continues to drive research and practice related to the preparation and development of school leaders. The purpose of this study was to explore identified determinants of effectiveness (Darling-Hammond, et al., 2007) in addition to students’ perception of leadership preparation program effectiveness. Using the responses of two cohorts on survey questionnaires, the data was analyzed, first through the research identified elements of effectiveness then through select subjective measures (scales) informing us of student sense of well-being. The findings showed correlational support for the need to consider student sense of preparedness through positive subjective measures, particularly as student sense of accomplishment in leadership preparation influences leadership practices, teaching and learning, and ultimately school outcomes.