Today's college students increasingly need skills in social media and teleworking. To develop these skills, instructors at four institutions created and implemented a cross-institutional group project that required students to create and share online an instructional video about a social media topic. Students then discussed the videos and their teleworking experience through subsequent cross-institutional Twitter chats. Based on the results from this study, suggestions are offered for helping students learn through teaching and discovering the benefits and drawbacks of teleworking.