Underperformance is a significant challenge for surgical educators. This paper outlines some educational strategies to manage the very complex demands presented by underperformance during training in the workplace. Preventative approaches include: setting expectations with early conversations; conscious attention to the workplace curriculum; and building trainee evaluative judgement through assessment and feedback. Once underperformance has been identified, other approaches including: developing a joint action plan; reducing or increasing feedback opportunities; and ensuring the trainee remains motivated. While these strategies cannot prevent failure, they offer the trainee opportunities to succeed.