Background Transitioning from trainee to independent surgeon is challenging, with teaching and mentoring learners adding complexity. This study aimed to identify benefits and challenges of teaching and mentoring residents early in surgical practice. Materials and Methods A mixed-methods survey with multiple choice and open-ended questions was developed for early career (first 3 years) and experienced (more than 3 years) surgeons working with residents. The survey was initially piloted by 6 surgeons, revised according to feedback and distributed on Twitter. Quantitative and qualitative analyses were performed. Results Seventy-three valid responses were analyzed, 21 (25%) from early career surgeons and 53 (75%) from experienced surgeons. The majority were women (62%), practiced in academics (78%) and lived in the United States (76%). Most of the early career and experienced surgeons selected the operating room as the most teaching challenging location (62% early career; and 60% experienced). Top teaching challenges of early career surgeons were the need to focus on own skills (24%) and concern for patient safety/outcomes (24%), while experienced surgeons reported need to focus on own skills (23%) and difficulty giving up control (23%). Open-ended responses identified themes related to teaching and mentoring. Comments highlighted benefits of organizational support to facilitate teaching and mentoring and negative experiences due to resident learners not respecting early career surgeons. Discussion This pilot study explores an area not previously studied. Early career surgeons and experienced surgeons find many similar challenges and benefits of teaching and mentoring residents. Challenges and themes identified can guide early career surgeons and organizations with regard to teaching and mentoring.