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Expectations of certainty and confidence in surgical culture are a source of internal conflict for surgeons and learners, with surgeons describing a pressure to project an image that is, at times, inconsistent with how they feel internally. The authors explored surgical residents’ perceptions of “impression management” and its effects on surgical judgment and decision making.The authors used a constructivist grounded theory approach to conduct and analyze 15 semistructured interviews with general surgery trainees at an urban Canadian academic health center between 2012 and 2014. Interviews explored impression management in the context of resident learning and performance. Analysis was inductive, whereby emergent themes contributed to a developing conceptual framework, and deductive, using an existing theory of impression management.Residents described sensing an “expectation” to portray an image aligned with the ideal surgical stereotype of confidence and certainty, and shared strategies used to mirror this image. Impression management strategies were used to portray an image of competence, with the aim to improve access to teaching and evaluations. Unintended consequences of impression management on decision making, patient safety, and resident wellness were identified.These findings contribute to a deeper understanding of the potential impact of the sociocultural context on residency training, and provide a language allowing for more explicit discussions about the impact of surgical culture on trainee behaviors. Translation includes formal instruction of these concepts in the curriculum so that trainees better recognize, reflect on, and cope with the pressures to perform in front of others.