Digital conversation spaces have the potential to generate powerful collective intelligence, but only when users are thoughtful, reflective, and have experience interacting with diverse ideas. To be able to engage in online conversational spaces in this way, though, is not inherent or natural: it must be practiced. This article will argue that it is essential to have adolescents practice engaging in challenging and professional conversations online with peers in classroom settings. Utilizing a New Media Literacy framework, this article will share impactful classroom practices that help adolescents develop effective online conversation skills. Essential to this pedagogy is a cycle of reflection, where students are asked to revisit their contributions to prior digital conversations and consider the impact that that prior contribution had on the conversation and the community. Asking students to reflect not on how to be kind (as most fear-based "digital citizenship" curriculum does) but rather on how contributions inform, persuade, and otherwise move the conversation forward, helps adolescents to develop a powerful online conversational presence.