Surgical training requires rigorous diligence, effective communication, and timely escalation to ensure patient safety. Recent focus on psychological safety and wellbeing has coincided with increased reluctance to provide corrective feedback or address underperformance. This abstract explores how avoiding difficult conversations contributes to training gaps, unacknowledged workload transfers to senior clinicians, and heightened patient risk. The analysis evaluates whether aspects of the hidden curriculum inadvertently delay the development of responsibility and professional growth in surgical education. A narrative review was conducted across the literature on surgical education, patient safety, and organisational behaviour. Key themes were identified from studies examining handover failures, speaking-up behaviour, psychological safety, feedback avoidance, burnout, and the phenomenon of “failure to fail” underperforming trainees. Findings were synthesised thematically, with particular relevance to postgraduate surgical training environments. The literature consistently identifies communication breakdowns and inadequate handover as major contributors to preventable harm. Although psychological safety promotes reporting and learning, its vague definition may discourage timely feedback and accountability. Concerns about appearing punitive or unprofessional often lead to feedback avoidance. This dynamic reduces teaching capacity and delays skill acquisition among trainees. Early failure to address underperformance is linked to persistent competence gaps and increased stress during transitions to independent practice. Cultures that prioritise psychological safety without clear expectations may undermine both education and patient safety. Educational strategies that normalise early, specific feedback, define essential professional behaviours such as handover and ownership, and incorporate just-culture principles may help address these challenges.