Maintaining a roadmap is a crucial part for any organization that wants to keep the roadmapping process alive after its development. However, it is not easy to maintain and review a roadmap, because an organization is exposed to constant changes in its business environment. An organization has to review its roadmap to include the changes that have a significant affect on the status of the roadmap. But, to determine when it is time to review a roadmap is a major challenge for any organization. As a result, most organizations maintain a roadmap on a predetermined regular basis. This paper proposes an analytical approach and evaluation model to determine the status of a roadmap. The proposed approach will assist an organization to decide when a review of its roadmap is necessary. A case sample is presented to demonstrate the computational process and applicability of the proposed approach.