This paper presents our experiences in evolving the Virtual Objective Structured Clinical Exam (VOSCE) system. This system allows medical students to experience the interaction between a patient and a medical doctor using natural methods of interaction with a high level of immersion. These features enable the system to provide training on medical communication skills. We discuss the experiences of a group of medical and physician assistant students that pilot tested the system. Further, we examine the impact of evolving the system based on their feedback. The VOSCE system's performance in subsequent studies has indicated that end-user feedback improvements have significantly impacted overall performance and efficacy.