Struggling learners often require interventions that are time-consuming and emotionally exhausting for both the trainee and faculty. Numerous barriers, including lack of resources, faculty development, and fear of legal retribution, can impede medical educators from developing and implementing robust remediation plans. Despite the large volume of literature citing professionalism education and the "hidden curriculum" as problem areas in medical education, frontline educators lack practical tools and empowerment to address unprofessionalism in trainees. The paucity of resources in this arena has led to decreased job satisfaction, increased burnout, and an exodus from academic medicine. Department leadership acknowledgment and investment in training faculty on remediation strategies for learners in difficulty and providing tools to meet these challenging job demands will improve faculty's job satisfaction and overall well-being. The authors review salient literature and methodology for diagnosing learners in difficulty, with focus on a high-yield, pragmatic approach that can be taken by medical training programs, including those that lack a robust medical education infrastructure.