Discussion is a crucial component for learning in a college classroom. Increasingly, university and college faculty are using online learning management systems to facilitate and assess course discussions. Given this reality, are there ways to frame prompts to generate normatively better discussions, or discussions where students are better able to meet the course learning outcomes? To answer these questions, we utilize data from Introduction to American Government classes at two institutions with the students of three instructors who participated in online discussion boards on multiple substantive topics; for each topic, students were randomly assigned to one of two experimental conditions. In each, we framed a related prompt in different ways to test how such prompts impact student success as measured by several learning outcomes informed by the American Association of Colleges & Universities (AAC&U). With our unique experimental design and novel data, we are able to test several hypotheses related to student engagement, the content of discussions, as well as the quality of students' work. In the end, our research has important normative implications for pedagogy as well as the cultivation of civility and political engagement inside and outside of the modern classroom environment.