In this essay Heidi Elemendorf and John Ottenhoff discuss the central role that intellectual communities should play in a liberal education and the value of conversation for our students, and we explore the ways in which web-based conversational forums can be best designed to fully support these ambitious learning goals. Coming from very different fields (Biology and English Literature) and in different course contexts (Microbiology course for non-majors and Shakespeare seminar), they nonetheless discover core values and design issues by looking closely at the discourse produced from online discussions. Centrally, they connect what they identify as expert-like behavior to the complexities of intellectual development in conversational contexts.