The traditional Halstedian model of surgical education lacks that nuanced and holistic approach required to manage surgical residency performance. The growing complexity of the medical system, coupled with diverse institutional resources and cultures, poses significant challenges to delivering high-quality surgical education with consistent accountability and effective evaluation. Program leadership must balance standardization with individualized support. This chapter explores methods to identify and address performance issues among residents and faculty through a combination of standardized tools—Accreditation Council for Graduate Medical (ACGME) milestones, Entrustable Professional Activities (EPAs), and structured assessments—and strategies that foster a culture of communication, coaching, and psychological safety. This chapter explores methods to identify and address performance issues including expectation setting, value-aligned recruitment, addressing bias, and the use of multi-modal evaluation techniques including simulation, video review, and self-reflection. Emphasis is placed on early identification of performance concerns, understanding root cause, and developing remediation plans grounded in communication, coaching, and emotional intelligence.