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The purpose of our study was to describe and explain the experiences of Indigenous teachers during their leadership preparation to become school or tribal education administrators. We looked at a range of participants’ experiences in the university’s existing leadership preparation program and the Indigenous Administrators and Leaders (IAL) program. We used a qualitative case study design to look at the experiences of two Indigenous teachers during their journey to become administrators. A participant survey was the primary data source. For analysis, we used In Vivo coding to capture the participants’ voices and pattern coding to identify themes. Based on our analysis, we identified key themes: the centrality of relationships, notions of time, and misalignment of expectations.