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This school-university collaborative research measured employee and student wellbeing at a Canadian school. The first two stages of the Appreciative Inquiry (AI) 4-D process ‘discover’ and ‘dream’ were adopted to co-create two online surveys which participants volunteered to complete according to University ethics approval. The paper reports on the wellbeing of 187 employees and 797 male students (aged 11-18). Categorical questions, wellbeing items via n-point Likert scales, and open-ended answers were analysed. Results generated descriptive data displayed via bar plots, and open-ended questions focussed on participants’ perceptions of their current wellbeing and understandings about what wellbeing meant to them. The findings informed school decision-making, policy development, best-practice strategies, and curriculum enhancement, to strengthen school culture and advance operations.