Futures Literacy is the capability to imagine and understand potential futures to prepare ourselves to act and innovate in the present. This pilot study aims to understand how artistic methodologies and speculative design can support the collaborative exploration of futures in the context of work and contribute to developing peoples' capability of futures literacy. Our premise is that technologies such as Artificial Intelligence and the Internet of things can augment people and support their needs at work. To illustrate this process, we have presented a collaborative method that integrates an artistic intervention with speculative design activities. We tested the method in a full-day workshop with seventeen (17) participants from a Swedish academy responsible for enabling learning and competence development at work in the healthcare sector. The results indicate that the artistic intervention, combined with the speculative design activities, can challenge current participants' perspectives and offer them new ways of seeing futures with technologies. These new ways of seeing reveal underlying premises crucial in developing the capability of futures literacy. © The Author(s)