Background: Transitioning from trainee to attending surgeon requires learners to become educators. The purpose of this study is to evaluate educational strategies utilized by surgeons, define gaps in preparation for operative teaching, and identify opportunities to support this transition. Methods: A web-based, Association of Surgical Education approved survey was distributed to attending surgeons. Results: There were 153 respondents. Narrating actions was the most frequently reported educational model, utilized by 74% of junior faculty [JF] (0–5yrs) and 63% of senior faculty [SF] (>6yrs). Other models used included educational time-outs (29% JF, 27% SF), BID teaching model (36% JF, 51% SF), and Zwisch model (13% JF, 25% SF). Compared with 91% JF, 65% SF reported struggling with instruction (p < 0.001). Five themes emerged as presenting difficulty during the resident to attending transition: lack of relationships, ongoing learning, systems-based, cognitive load, impression management. Conclusions: Our results represent a needs assessment in the transition from learner to educator in the OR.