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Given the increasing number of culturally and linguistically diverse (CLD) students in our nation’s schools (NCES, 2020), we need teachers and school leaders who teach in inclusive and socially just ways. In this qualitative case study (Merriam & Tisdell, 2016), we paired up two different cohorts of leader candidates (LCs) and teacher candidates (TCs) in a series of collaborative conversations focused on culturally sustaining, socially just pedagogy (CSSJP) (Authors, 2018, 2021), to learn more about how bringing teacher and leader candidates together may support their understandings of enacting CSSJP. Collaborative conversations may help TCs and LCs share the responsibility of doing the challenging, but necessary, work of enacting CSSJP – work that is too big and important to shoulder alone.