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Massachusetts leadership preparation standards call on candidates to develop the competencies, strategies, and mindsets needed for anti-racist leadership (MA Department of Elementary and Secondary Education, 2021). Findings from in this paper, drawing on a longitudinal study of leadership candidates in one preparation program, demonstrate the differences between the development of these competencies, strategies, and mindsets between two veteran teachers who experienced the same leadership preparation program. Differences in ethno-racial background as well as a developmental ability to focus both on one’s personal mindset as well as anti-racist competencies and strategies that directly affect students emerged and have implications for differentiation within leadership preparation even when that preparation has a specific focus on developing anti-racist leadership practices.