Health-care reform, market competition, cost containment, and pressure for productivity have dramatically impacted the practice of orthopaedic surgery and academic surgical training. Orthopaedic leaders and training programs are striving to identify and solve these contemporary challenges. Herein, we focus on 4 areas that currently pose important challenges to modern orthopaedic surgical departments and academic hospital systems, including the demanding and evolving skill sets that are required of physician leaders, the effects of the changing medical-legal environment on academic medicine, the impact of increased clinical productivity emphasis on surgical education, and departmental leadership transitions.