This chapter introduces cultural hermeneutics as a lens for understanding philosophies of inquiry in distributed work groups. The authors suggest that philosophies of inquiry can be ascertained through hermeneutic analysis of written texts created by distributed workers using computer-mediated communication systems. Using this approach, elements of context in written artifacts that should be evident for each of Churchman’s inquiring models (Leibnizian, Lockean, Kantian, Hegelian, and Singerian) are delineated, which should help identify the underlying philosophies of inquiry being used by a particular group. Sample texts for each inquiring model are also presented. Understanding philosophies of inquiry can both guide the design and implementation of computer-mediated communication systems used to create knowledge and illuminate best practices for their use.