The history of instructional supervision has been relatively constant. From the days when the first colonists arrived and established schools for their children until today instructional supervision has consistently focused on the critical examination of a teacher’s classroom behavior with the assumption that supervising individual teachers could significantly improve teaching and learning throughout a school system. That assumption has proven to be flawed. The author believes that the focus of instructional supervision needs to shift off of individual teachers to focus on transforming the organization design and functioning of entire school systems. Instead of observing teachers working in their classrooms a re-imagined instructional supervision process would focus on transforming three sets of key system variables: Transform the system’s environmental relationships, transform the system’s core and support work processes, and transform the system’s internal social infrastructure. Supervising Knowledge Work describes the salient features of a re-imagined supervision process called Knowledge Work Supervision that is designed to transform entire school systems.