In recent years a host of new agile software development methodologies have been introduced. These methodologies emphasize people over process, software over documentation, customer collaboration over contract negotiation and responding to change over following a plan. They are quite different from the traditional process oriented approaches. One major implication of these differences is the need for a less rigid and formal approach to project management. This paper describes leadership characteristics that are conducive to agile software development environments and maps these characteristics to Churchman's five modes of inquiry. With agile's focus on people over processes, it is critical to a project's success to have the right types of people "leading the charge". By mapping desirable characteristics of agile leaders to specific inquiry modes, the goal of this paper is to provide insight into the types of managers that are most likely to be successful in an agile environment.