This study postulates that an empowered workforce can rally the organization to the objective of achieving IT planning effectiveness within the premises of a planning culture geared to empowerment. The planning culture is a powerful lever to empower knowledge workers and establish a learning environment conducive to planning effectiveness. A sample of 101 IT professionals was used to look at the indirect effects of the planning culture on IT planning effectiveness through the empowerment of knowledge workers. Strong support was garnered for the three hypotheses of the study, namely: (1) empowered knowledge workers make a significant impact on the quality of planning outcomes; (2) planning cultures empower knowledge workers; hence, (3) improving the quality of planning through the motivational path of knowledge workers empowerment. Implications of the findings for organizational learning are discussed at the end.