Objective: Due to its comprehensive, reliable, and valid format, the objective structured clinical examination (OSCE) is the gold standard for assessing the clinical competency of medical students. In the present study, we evaluated the importance of the OSCE as a learning tool for postgraduate (PG) residents assessing their junior undergraduate students. We further aimed to analyze quality improvement during the pre-coronavirus disease (COVID) and COVID periods. Methods: This quality-improvement interventional study was conducted at the Department of Obstetrics and Gynecology. The PG residents were trained to conduct the OSCE. A formal feedback form was distributed to 22 participants, and their responses were analyzed using a five-point Likert scale. Fishbone analysis was performed, and the ‘plan-do-study-act’ (PDSA) cycle was implemented to improve the OSCE. Results: Most of the residents (95%) believed that this examination system was extremely fair and covered a wide range of clinical skills and knowledge. Further, 4.5% believed it was more labor- and resource intensive and time-consuming. Eighteen (81.8%) residents stated that they had learned all three domains: communication skills, time management skills, and a stepwise approach to clinical scenarios. The PDSA cycle was run eight times, resulting in a dramatic improvement (from 30% to 70%) in the knowledge and clinical skills of PGs and the standard of OSCE. Conclusion The OSCE can be used as a learning tool for young assessors who are receptive to novel tools. The involvement of PGs in the OSCE improved their communication skills and helped overcome human resource limitations while manning various OSCE stations.