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Medical students’ specialty selection is strongly influenced by highly rated faculty, resident educators and mentors. Income, lifestyle, personality attributes, and intellectual content are particularly important factors. However, the reactions of faculty and residents medical students interact with during clerkship have not yet been explored. The study sought to understand the effect of faculty and resident feedback to medical students upon disclosure of their specialty selection. A validated 41-item survey was developed to gather medical student experiences with faculty and resident feedback regarding specialty selection. The survey was distributed in March 2021 via Qualtrics. There were 329 surveys included in the analysis. A total of 41% of students felt uncomfortable sharing their specialty selection with faculty and residents. Fear of judgments, grades, and retaliation were reported as reasons medical students were not comfortable with sharing their decision. It was reported that 26.8% of medical students changed their specialty selection following negative feedback from faculty or residents. Family medicine applicants reported the highest proportion of negative feedback from different specialty faculty (20%) and residents (24%). Surgical specialties received the most positive feedback regardless of the faculty or resident specialty. The findings show many medical students report discomfort about sharing their intended specialty with faculty and residents. For medical student who do share their career trajectory, faculty and resident feedback plays an important role.