This chapter discusses issues and challenges encountered in using large-scale data sets to study educational experiences and subsequent outcomes for American Indian and Alaska Native (AI/AN) students. In this chapter, we argue that the linguistic and cultural diversity of Native peoples, coupled with the legal and political ways in which education has been used to acculturate and assimilate them, makes it imperative that a full range of social, cultural, and demographic variables be collected and that these data be analyzed, using a theory of change that emphasizes the strengths of AI/AN students and their communities rather than their perceived deficits. We envision this theory of change espousing the use of data to critically unpack and respond to the role of language and culture in shaping pathways to success in education and beyond for AI/AN students. We conclude with recommendations for constructing and analyzing large-scale data sets to better represent the diversity of cultures and experiences among AI/AN students.