Purpose: This article examines the experiences of urban, public school principals noted for their instructional leadership and highlights a leadership approach grounded in a learning imperative. Framework: This article explores the concept of instructional leadership, defined as attending to instructional matters, as embedded in an urban public school district characterized by a managerial context. Based on common themes in the data, this article adds to the extant literature on leading for learning by putting forth the concept of a learning imperative for consideration. Research Methods: This qualitative, interpretive, multicase study of 18 New York City K-12 public school principals applied purposeful sampling by soliciting and vetting nominations from supervisors, staff, and students/parents. Evidence included interviews, time surveys, observations, and document analysis. Findings: Data analysis and interpretation characterized participants’ work contexts as consistent with a managerial imperative and highlighted limitations to the phrase "instructional leadership." Further analysis found that participants followed a leadership approach grounded in a learning imperative, defined as a principal’s obligation to prioritize, attend to, and act on matters of learning. Participants’ perspectives and actions on a learning imperative followed two common themes: (a) grounding the purpose of a school in learning and (b) valuing and fostering the learning and professional growth of the adults working with the school’s students. Implications: Findings contribute to the instructional leadership and leading for learning literatures by placing learning in the forefront and emphasizing the need to prioritize learning. Suggestions for ways to operationalize a learning imperative are provided.