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In this paper, we study how 30 school districts of varying size, structure, and leadership needs approached the planning and developing of principal pipelines within the context of a national initiative. We identified five central office features and conditions that emerged as most pivotal to districts’ ability to make progress in pipeline development: integration of the pipeline work across departments; organizational location of the pipeline work; superintendent support; alignment of the pipeline with district strategic initiatives; and the expertise, autonomy, and authority of the pipeline planning team members. Findings demonstrate the importance of organizational structure to successful implementation of the pipeline and imply the need for districts to cultivate awareness of their organizational leverage points as they undertake the work.