The environment has changed markedly over the past 30 years in medicine in general and specifically in academic surgery. This changing landscape has presented significant new challenges to surgical department chairs, and the challenges fall into several major categories. The financial category includes changes in third-party payment systems, managed care, and decreasing Medicare and Medicaid reimbursements. At the same time, the regulatory burden is increasing along with requirements for documentation, more stringent labor protection laws, changes in the status of residents either as employees or students, the Health Insurance Portability and Accountability Act, and increasing outcome-reporting requirements. In addition, market forces have significantly altered the health care landscape with the rise and prevalence of for-profit hospital and provider networks and boutique hospitals and overall increasing competitiveness between academic medical centers and private nonteaching medical centers. Today’s surgical chair must master an ever-expanding business vocabulary. Benchmarking is the key term of the day, whether in financial performance, compensation models, length of stay, case mix index, or clinical outcomes.