Chander, AjayBarijough, Sanam MirzazadOkubo, Yuko2017-07-242017-07-242017Enterprises globally are seeking out and leveraging digital technologies to improve their performance and competitiveness. As data-driven personalization becomes an increasingly ubiquitous aspect of our digital experience, we believe it is likely that the rapidly digitizing workplace will explore systems for personalizing the support their employees receive. In this paper, we present our experience designing and experimenting with a pilot service that provided personalized digital tool recommendations to enterprise users, for work-related issues. This Enterprise Assistant service, or EAS, was offered for 10 weeks and served 24 users within the same enterprise. Users emailed the EAS with their questions and received personalized suggestions and follow-ups until their issue was resolved. The service addressed a variety of issues during the experiment, with a majority of users expressing interest in continuing to use it. One key finding is that user awareness of friction points in their daily workflows is quite low, leading to significant communication overhead simply to uncover an actionable issue for the EAS. We channel our findings towards design guidelines and opportunities for systems that aim to empower employees with personalized tools in our rapidly digitizing workplaces.enText/Conference Paper10.18420/ecscw2017-202510-2591