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This study details a participatory process to develop a Theory of Change (ToC) and evaluation agenda for Compassionate Systems Leadership (CSL) in British Columbia (BC), Canada. Guided by van Es et al.’s (2015) eight-step ToC framework, qualitative data were collected from 23 CSL-trained educators via surveys, with 17 participants also taking part in in-depth interviews. A hybrid deductive–inductive coding strategy was used, with analysis conducted in Dedoose (v9.9.22) to ensure thematic coherence and analytic rigor. Key change pathways and a responsive evaluation agenda were identified. Thick, emic description was supported through the MIRACLE framework (Younas et al., 2023). Findings enhance understanding of CSL’s transformative potential and offer methodological contributions to evaluating interventions for systems change in educational settings.