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We present the results of an ongoing, multi-phased study examining the work and wellbeing of Saskatchewan school administrators during and beyond the heights of the pandemic. We draw on the Job Demands-Resources (JD-R) model to highlight the substance and scope of work that contributed to wellbeing issues among Saskatchewan school administrators during the pandemic and the extent and kinds of wellbeing issues these administrators continue to experience three years later. We posit that strengthening leadership capacity to inspire future confidence in the school principalship requires a reorientation of our understanding of what it means to be a leader and the creation of an environment wherein incumbents and aspiring administrators feel secure in demonstrating vulnerability and advocating for their own needs.