Information systems research has been concerned with improving task-related performance. The concept of fit is often used to explain how system design results in better performance and overall value. So far, the literature focuses mainly on performance evaluation criteria that are based on measures of task efficiency, accuracy, or productivity. However, nowadays, productivity gain is no longer the single evaluation criterion. In many instances, computer systems are expected to enhance our creativity, reveal opportunities and open new vistas of uncharted frontiers. To address this void, we introduce the concept of generativity and develop two corresponding design considerations--"generative capacity" that refers to one’s creativity, ingenuity and mental dexterity, and "generative fit" that refers to the extent to which an IT artifact is conducive to evoking and enhancing that generative capacity. We offer an extended view of the concept of fit and realign the prevailing approaches to humancomputer interaction design with current leading-edge applications and users' expectations. Our findings guide systems designers who aim to enhance creative work, unstructured syntheses, serendipitous discoveries, and any other form of computer-aided tasks that involve unexplored outcomes, expect fresh configurations or aim to enhance our ability to boldly go where no one has gone before. In this paper, we explore the notion of generativity, review its theoretical background in the context of the social sciences, and argue that it should be included in the evaluation of task-related performance. Then, we briefly explore the role of fit in IS research, position “generative fit” in that context, explain its role and impact on performance, and provide key design considerations that enhance generative fit. Finally, we demonstrate our thesis with an illustrative case of good generative fit, and conclude with ideas for further research and final thoughts.