Brazilian higher education institutions face a complex and challenging environment as the national market in education is becoming more competitive. International investment, a decrease in the population of potential students, and the proliferation of innumerable small institutions add to this complexity. Organizations are becoming flatter and the key managers within them are deans. Although deans are required to act as managerial experts, they are usually selected from the teaching body of the institution. In this paper, a group of deans from a large private institution gave their self-assessment of their academic and managerial skills. The results revealed that they tend to have a high perception of their managerial skills, even though they have no previous managerial experience or formal training. This underlines that senior academic administrators cannot simply assume that deans, by the nature of their work environment, are proficient in managerial skills; neither that they can easily identify inadequacies nor have them self-corrected. To accomplish the necessary institutional changes to face the complexities of the current globalized education market, a new assessment culture has to be implemented in the academic environment. (Contains 3 tables.)