Both consistent policy enforcement and excellent patron service are essential in library Circulation departments. But when strict enforcement of policy impedes excellent service, what takes precedent in a given interaction? What does the library value, and how do staff develop the empathy, flexibility, and confidence necessary to make decisions in the moment based on those values? This session will describe a multi-month, interactive, reflective staff training initiative intended to let staff (both individually and collectively) grapple with diverse patron circumstances that defy the assumptions and expectations reflected in our written policies. Program development and implementation will be addressed, including details of the various "missions" staff completed and the incentives offered along the way to increase engagement. Assessment of program success and next steps will also be discussed. Attendees will acquire new ideas about training personnel in their own libraries to balance the priorities of fair enforcement and flexible empathy.