Research suggests that over time Information Systems (IS) behavior can become routinized, making it difficult to extend one’s use of an IS or improve work processes. To disrupt habitual IS use behavior and its inertial consequences, one of the key behavioral modification tools used in organizations is feedback. However, we know little about how feedback impacts changes in individual use of IS in organizations. This paper examines the role of the feedback environment (ie valence, amount, quality and timing of feedback) on variations in IS use, ie, experimenting with different ways of using an IS for one’s work. As a first step, this study proposes a conceptual model of feedback in IS use, grounded in Generalized Darwinian principles of evolutionary change. Using data from 86 users of Learning Management Systems, the preliminary results suggest the importance of various feedback mechanisms for encouraging variations in how IS is used by individuals.