Modern digital work environments allow for great flexibility, but can also contribute to a blurring of work/life boundaries and technostress. An emerging class of intelligent tools, that we term Digital Productivity Assistant (DPA), helps knowledge workers to improve their productivity by creating awareness of their collaboration behaviour and by suggesting improvements. In this revelatory case study, we combine auto-ethnographic insights with interview data from three organisations to explore how one such tool works to influence collaboration and productivity management behaviours, using the lens of persuasive IS design. We also identify barriers to DPAs’ effective use as a partner in personal productivity management.