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Qualitative education researchers often give good guidance on interviewing students, teachers, and principals. However, less guidance exists for interviewing researchers, coaches, district leaders, and philanthropists—what can be collectively termed “educational experts and elites.” Using the case of 73 interviews across Chicago, Philadelphia, and New York City, I outline key aspects for guiding these types of interviews. First, I show practical considerations for accessing, gaining trust, and preparing for these interviews. Second, I detail core differences with traditional school interviews in terms of anonymity, question structure, historical specificity, and attention to interpersonal connections. Third, I outline the opportunities with expert and elite interviews, particularly as these interviews can provide a broader perspective with a longer time horizon, an attention to larger socio-political contexts, and access to information that can shed new light to old questions. Finally, I offer caveats and practical solutions for potential pitfalls with interviews that give inaccurate information, have conflicting perspectives, and paint one-sided caricatures. This methodological piece will be particularly useful for scholars of educational leadership, policy, and politics.