The purpose of this pilot study was to examine our hypothesis that enriching workplace emotional intelligence through resident coaches could improve third-year medical students' adaptability and proactivity on the Obstetrics and Gynecology clerkship.An observational pilot study was conducted in a teaching hospital. Fourteen 3rd year medical students from two cohorts of clerkships were randomly divided into two groups, and equally assigned to trained resident coaches and untrained resident coaches. Data was collected through onsite naturalistic observation of students' adaptability and proactivity in clinical settings using a checklist with a 4-point Likert scale (1=poor to 4=excellent). Wilcoxon rank-sum test was used to compare the differences between these two groups.A total of 280 data points were collected through onsite observations conducted by investigators. All (n=14) students' adaptability and proactivity performance significantly improved from an average of 3.04 to 3.45 (p=0.014) over 6-week clerkship. Overall, students with trained resident coaches adapted significantly faster and were more proactive in the obstetrics and gynecology clinical setting than the students with untrained coaches (3.31 vs. 3.24, p=0.019).Findings from our pilot study supported our hypothesis that enriching workplace emotional intelligence knowledge through resident coaches was able to help medical students adapt into obstetrics and gynecology clinical settings faster and become more proactive in learning. Clerkship programs can incorporate the concept of a resident coach in their curriculum to help bridge medical students into clinical settings and to help them engage in self-directed learning throughout the rotation.