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This article contributes to an emergent literature of empirical studies on how emotion impacts leadership. The purpose of the study was to examine how secondary school administrators derived meaning from critical incidents of significant emotional events retrospectively, and how the understanding impacted leadership. A conceptual framework of emotion as a critical element of leadership, and emotion as an element of authentic leadership, was used for sensitivity in examining and analyzing the data from a multi-case study with nine practicing USA secondary school administrators. Four themes relating to emotion in leadership were found, and a model was conceptualized. The article concludes with recommendations for further research.