Recent advances in systems theory have significantly raised its utility for supporting problem-structuring activity in organizations. However, this approach has been inadequately developed for representing and evaluating the nature and outcomes of organizational functioning. Toward that end this paper introduces a new method, called interpretive systems analysis, which incorporates ideas from semiotic theory. Using this method, the complex web of agents, actions, means, and circumstances in organizational functioning may be analytically discriminated into multiple courses of action that are emphasized on dimensions of legitimacy, motivation, and power. An integrative appraisal of key elements and factors shaping organizational performance may then be achieved through the formulation of “systems of significance,” formed of oppositional and associative relations. Organizations can thus be illuminated in terms of principle inconsistencies and tensions shaping their operations. The application and utility of this method is illustrated through a case study of customer service operations.