This study is located in the area of university work-integrated learning (WIL) management, in particular the implementation of both placement and non-placement WIL. The focus of the study is on enhancing WIL coordinators’ understanding of WIL as a system, using activity theory as a framework, and to mobilize this understanding to address challenges in practice. To this end WIL coordinators at two South African universities attended WIL challenge workshops in which an activity system-derived diagnostic toolkit was introduced. The verbal discussions and diagrams presented by the coordinators were analyzed for evidence of systematic understanding of WIL, challenges and future possibilities. Findings from the study revealed that WIL coordinators successfully used the toolkit to identify system-level constraints and were inspired to engage in further investigations. The authors thus argue that the diagnostic toolkit could be used with WIL coordinators at other universities as a useful approach to understanding and optimizing their WIL practices.