This report offers political advice to school superintendents. The authors draw solely on a collection of anecdotes from superintendents of large urban districts to offer a narrative replete with maxims, aphorisms, and pithy advice. Superintending is, in their view, a continuous string of almost unavoidable conflicts, so the reader is led through internal groups (central office, school board, unions, teachers and principals) and external groups (foundations, businesses and state politicians) and advised on how to cultivate support and deal with opponents. There is no research design, literature review, or systematic data collection. The report relies heavily on the authors’ experiences, yet neither author appears to have worked in a K-12 district or served as a superintendent. Moreover, the advice that follows is often contrary to contemporary professional practices. The report improperly generalizes from more politicized large urban districts and does not consider how the favored approaches may limit vision, flexibility and effectiveness. In the end, the report perpetuates antiquated methods and does not advance our knowledge.