This article presents a systematic approach to prioritize requirements and estimate risk associated with each requirement. It first aims at providing short training to both developers and stakeholders to bridge the gap of understanding and comprehend requirements so that a refined priority value for each requirement can be obtained. Secondly, it presents a requirement risk and re-prioritization estimation model to make sure that a right decision has been taken by stakeholder and developers. The entire process has been supported with an example case study and by a survey that is conducted at IT companies. The response for the applicability of the proposed approach from the industry is appreciable and is promising as it will help in minimizing the disagreements between stakeholders and developers, thereby resulting in better collaboration. It will also help in minimizing the overall risk associated with development as only the most important functionality will be delivered in right sequence to the client thereby reducing the overall development time