How does a dean or department or division chairperson fit into the administrative structure of a community college? How do these middle managers best work with faculty? These are questions that have evolved in community and technical colleges, as they moved into this new century. The roles of the middle manager will vary by campus throughout the United States or Canada. They vary somewhat depending upon the size and type of institution. Their roles are, however, similar in nature when one looks at the key expectations: (1) personnel role; (2) student support role; (3) budgeting role; (4) development of improvement opportunities; and (5) strong personal traits. These major roles of middle managers are both challenging and difficult. Persons in these positions depend upon support from their chief academic officer (CAO), president and board of trustees. Some of their roles are also somewhat predetermined by the curricula, courses of study and mission of the college in which they work. This article discusses the key expectations in a middle manager.