<p>This paper describes a research study to improve the benefits realization of a company’s knowledge management system. We conducted the research from a social theory research perspective to uncover how to work towards convincing users to use the system willingly and appropriately, i.e., as intended, to maximise its benefits realization. We used critical social heuristics to plan and reflect upon potential improvement actions. It enabled critical thinking to develop, and reflect upon, guidelines to enhance stakeholder engagement and persuade users to adopt the system and use it as intended. Knowledge management enables organizations to effectively manage the organizational knowledge as a corporate asset. When implemented appropriately, it gives organizations a competitive edge. However, it is often not used as intended and can, accordingly, become expensive file storage systems, rather than valuable knowledge management systems. In the company where we conducted this study, a knowledge management system was used as intended by some employees. On the other hand, some employees resisted using it and/or used simply to store documents. It was thus not used as intended by all employees, so the full benefits of knowledge management did not realize. By exploring the system’s dimensions of motivation, control, knowledge, and legitimacy (as per critical social heuristics) from the perspectives of end-users, guidelines for improvement of knowledge management system adoption were derived—the guidelines can be used to increase stakeholder engagement and, accordingly, suitable use, along with benefits realization, of these systems in similar organizations.</p>