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Objective This article describes a formal ophthalmology residency mentorship program, identifies its strengths and weaknesses over 5 years of implementation, and proposes strategies to improve qualitative outcomes of the mentorship program. Design Cross-sectional anonymous online survey. Subjects All current and former mentees and mentors at the Casey Eye Institute (CEI) residency program from 2016 to 2021. Methods All eligible participants were contacted via email to complete a survey to describe and analyze their experiences with the CEI's formal residency mentorship program. Results Of the 65 surveyed participants, 82% preferred in-person meetings and met up from 2 to 3 times (44%) to 4 to 6 times (38.5%) annually at 15 minutes to 1 hour (48%) or 1 to 2 hours (42%) duration. Sixty-two percent of meetings were initiated by mentors, 8% by mentees, and 32% shared responsibilities equally. Participants also identified the three most important qualities for successful mentor-mentee relationship as personality (33.6%), communication styles (29.2%), and extracurricular interests/hobbies (16.8%). Mentees valued career advising, networking, and wellness support over academic and research mentorship. Subjective outcomes showed 25% of the mentee and 43% of the mentors agreed the mentorship program was a valuable experience. Comparably, 14% of the mentees and 38% of the mentors prioritized the relationship. There was a strong correlation between participants who prioritized the relationship and acknowledged it as a valuable experience (p Conclusion Our survey identified that weaknesses of the mentorship program include ineffective communications, inadequate preparation in their respective roles, and lack of priority focus on the relationship. We propose strategies to strengthen our program through creating workshops to clarify roles and responsibilities, emphasizing accountability with a contract statement, and implementing a new matching algorithm to customize participants' experience. Additional studies from other residencies with formal mentorship programs are warranted to identify, strategize, and foster high-quality mentorship.