The practice and industry of organizational coaching are now well established, but how it is understood theoretically continues to lag behind. In this paper we analyze possible reasons for this state of affairs and argue that the development of coaching as an academic discipline will benefit from adopting philosophical pragmatism as an overarching theoretical framework. This move will enable coaching academics to utilize the contributions to knowledge that different paradigms generate. Positioning pragmatism as a theory of action we argue that organizational coaching is by default a pragmatic enterprise and provide three examples of the considerable benefits to be gained by conceptualizing it this way. Drawing from the pragmatists’ ideas, particularly those of John Dewey, we demonstrate how the theoretical understanding of organizational coaching can be enhanced by considering its nature as a joint inquiry. Pragmatism suggests development as an ultimate purpose for organizational coaching which also helps to resolve fundamental conceptual debates. In light of the complexity and diversity involved in the way that organizational coaching is practiced, pragmatism offers coaches a useful framework for developing the flexibility required for navigating the multiplicity of influences on their practice.