When Chiquita Brands considered relocating its corporate headquarters, competing cities started Twitter campaigns to influence the decision by communicating directly with the chief executive officer. As he used the new microblogging channel, some of his previously private communication became public, some personal communication became professional, and some professional communication became personal. The case shows how social media can significantly affect chief executive officers’ communication by encouraging boundary crossing. Understanding the connections between the private versus public and personal versus professional rhetorical categories will help business communicators make wise choices as technology continues to introduce new social media and other channel options.