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This research explores New York State district and school leaders’ approaches to leadership during the COVID-19 pandemic. In this two-phase mixed-method study, educator surveys and case study field research of positive outlier schools (i.e., those with significantly better educator survey responses to the pandemic in terms of stress and job satisfaction) were conducted. The study found that schools where educators experienced lower levels of stress and changes in job satisfaction during the pandemic were also places where leaders empowered diverse stakeholders in problem-solving. The results suggest that leaders’ empowerment strategies contributed to their staff’s willingness and capacity to adapt. These results hold implications for leaders who seek to develop more adaptable schools and districts in preparation for future crises.