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This multiple case study illustrates and illuminates selected positive leadership practices (Murphy & Louis, 2018) employed by four members of the superintendency to successfully focus on learning and to deliver positive results within their school systems. Evidence is provided to support the assertion that thoughtful application of positive leadership principles can enable school and district leaders to flourish through collaborative, interconnected relationships as an effective way to share authority and responsibility within school and district environments. During particularly challenging times and increasingly complex demands this empiraclly grounded framework can illuminate pathways forward through reduced isolation and an improved sense of personal and organizational wellbeing.