Primary and secondary school students, college students, and corporate employees are all engaging more and more in some form of online or blended online/face-to-face education. Given the large number of pedagogical and design choices that we must make, however, where do we begin when designing new environments? This book argues that it is important for us to consider how technological design choices interact with pedagogical choices and cognitive states to affect learning behaviors. Specifically, this book focuses on synchronous, text-based chat and asks two questions: first, since research has often reported that chat environments promote conversational equity, which features of this technology seem to help create conversational equity; and second, how this change impacts the content of small group discussions. Using ethnographic-style observations and quasi-experimental studies, this book shows how changing conversational media influences (or does not) the resulting discussion among students. Based on these findings, Chatting to Learn examines the broader implications for the design of conversational environments, whether for educational or business use.