Effective communication of activities and progress in the workplace is crucial for the success of many modern organizations. In this paper, we extend current research on workplace communication and uncover opportunities for technology to support effective work activity reporting. We report on three studies: With a survey of 68 knowledge workers followed by 14 in-depth interviews, we investigated the perceived benefits of different types of progress reports and an array of challenges at three stages: Collection, Composition, and Delivery. We show an important interplay between written and face-to-face reporting, and highlight the importance of tailoring a report to its audience. We then present results from an analysis of 722 reports composed by 361 U.S.-based knowledge workers, looking at the influence of the audience on a report’s language. We conclude by discussing opportunities for future technologies to assist both employees and managers in collecting, interpreting, and reporting progress in the workplace.