One of the most important and yet more challenging and stressful tasks completed by a department chair is evaluating faculty. Regardless of its importance, though, department chairs often receive little or no training for this critical task. This paper contains three sections, all of which focus on faculty annual evaluations. The first section discusses a number of recommendations for conducting thorough and meaningful annual evaluations. The second section highlights a real case scenario at Auburn University in which all university departments were tasked with changing their evaluation procedures, criteria, and expectations for faculty performance to better align with the revised strategic goals and mission of the university. The third section highlights an innovative peer-based faculty performance-evaluation system employed in the department of kinesiology at the University of Maryland that is designed to engage all tenure-track faculty in the evaluation process.