Providing quantitative performance feedback to individual clinicians and clinical groups has been suggested as a useful strategy to reduce preventable morbidity and mortality within medicine. Anesthesiology groups wishing to design a program of quantitative performance feedback will encounter few published accounts of how such systems are influenced by their contexts and the features that promote effectiveness and usability. Two case studies are presented here which highlight how program design is related to context and perceived effectiveness. Design features which supported usability included prioritizing actionability when choosing metrics, involving the group or end-users during metric creation and goal setting and providing frequent communication of results. Contextual features which were found to support usability included resource availability, a mature safety and learning culture within the organization, and the provision of active leadership to create a sense of purpose, harness motivators and overcome barriers.