The ever-present “revolving door” syndrome, where education deans leave their posts within four to five years, served as the impetus for our research. We wanted to understand what we were doing as veteran deans that enabled us to exhibit a certain degree of resiliency with our job responsibilities. We adapted Eisner’s connoisseurship model (1991, 1998) and served as both a connoisseur and critic of our patterns of behavior over a six-year period. Eisner’s model explains that a connoisseur is able to identify the different dimensions of situations and experiences as well as their relationships. A connoisseur not only appreciates a situation but also critiques the same situation to help others see its subtle and not-so-subtle aspects.