OBJECTIVE: It is unknown what traits practicing surgeons value in those wishing to become colorectal surgeons. The objective of this study was determine the most common qualities used to describe applicants to colorectal surgery residency. DESIGN: Letters of a recommendation (LOR) qualitatively analyzed to determine how writers described applicants. Letters were analyzed, coded, and categorized to understand the qualities most admired and devalued by reviewers. SETTING: LOR submitted to Lahey Hospital and Medical Center in Massachusetts PARTICIPANTS: 111 applicants to colorectal surgery residency at Lahey during the 2019 to 2020 cycle including 658 letters and 409 letter writers. There were 315 standardized LOR and 343 narrative LOR. RESULTS: 75% of letters described some aspect of "grindstone" or hard-working attributes as being a positive. Other LORs valued attributes including being likeable and having good clinical and technical skills. The most frequent applicant flaws identified in the LOR included poor leadership skills and lack of delegation skills. Several letter writers also expressed concerns when an applicant was too soft spoken. CONCLUSIONS: This study codifies the qualities valued by letter writers in describing colorectal surgery applicants. The descriptors used by surgeons in LOR can be thought of as a portrayal of the qualities composing an "ideal surgical trainee." This cohort of LOR emphasized grindstone characteristics as a positive and poor leadership as a negative. As work-life integration becomes increasingly important to early career surgeons, intergenerational conflict may arise if the qualities lauded in the "ideal applicant" focus on work at all cost.