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Using a phenomenological inquiry style of interviewing, this case study examines how emotions and emotional responses inform an iterative process of meaning making to inform leadership efficacy. An assistant superintendent’s navigation of organizational change during a district crisis is analyzed in terms of emotions and emotional impact. Informed by social-psychological cognitivist theory, this study acknowledges the iterative nature of environment and emotional responses. Evidence suggests that emotional awareness, self-awareness, emotional influence, and promotion of positive psychological capacities were significant in the leader’s ability to foster a positive and effective work environment. Further, this study supports the argument for an emotional leadership focus in licensure programs as advantageous to leadership outcomes.