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In the effort to improve student outcomes, teachers are usually the focus of professional development efforts. However, research increasingly demonstrates the significance of the administrator in influencing student outcomes, raising questions about how they too should be involved in such programs. The study involved interviews conducted with 12 administrators engaged in a large-scale professional development program dedicated to equitable math instruction for diverse learners. The paper reports on their different understandings of diverse learners, perceptions of teacher needs, and approaches to support. While conventional professional development programs might focus on buy-in or normative frameworks, this paper argues for a situated approach to working with administrators, engaging with the complexity of their situation.