In recent decades, a number of training environments have moved toward program approaches targeting the development of competencies. Because of their complexity, monitoring the development of those competencies is a considerable challenge. Our hypothesis is that a computerized system could help overcome this challenge if it is well accepted by its users. We first summarize the context surrounding the implementation of such approaches. Next, we present a computerized assessment system established in the Family Medicine Residency Program of Laval University (Québec, Canada) that we have developed for tracking the development of residents' competencies. We then present the analysis of interactions between the system and users and the various proposals that were made to improve the system and longitudinal tracking of the development of the targeted competencies. We consider that this research provides useful guidelines for the computerized monitoring of learners' competencies development and for the design of such systems.