Wearable product/service solutions are increasingly spreading in everyday life aiming at supporting and tracking activities, also increasing self-awareness about behaviors and body parameters. The amount and variety of personal data generated and collected by these digital services is unprecedented in human history, and impacts on individuals, societies and organizations can now be only partly predicted. The design of data management in these solutions has so become a critical task for both designers and service providers. This paper presents the results of the application of a design tool, as part of an Impact Anticipation Method, created to foresee problems and opportunities so to improve design choices in quick design processes and design courses. The tool aims at stimulating the discussion on impacts related to the use of personal information. The results point out the usefulness of the method’s tool in raising awareness in designers, elicit critical thinking fostering the discussion on the topic, and provide insights for improvements. It demonstrates the need of more agile ways to address the topic in the design process. Students faced their lack of knowledge about how and when personal information is implied in their solutions, and on potential impacts that such information could have.