The role of dean in a business school is, by design, more strategic than tactical. And, when the various stakeholders that a dean must interact with are considered, the ability of a dean to have much of an operating knowledge of what is going on in the teaching and learning space of a school is very limited. The problem, however, is that the dean must be an advocate for this critical function of the business school mission. To understand how these two dimensions might be reconciled, this article looks at the drivers of a dean's perspective and the disengagement these drivers create. The article ends by suggesting ways for a dean to stay connected to this vital function of the school.