This thesis aims to explore how to shape proactive interactions between ambient artefacts and humans. Where ambient artefacts are represented by smart personal assistants and interactive tabletop robots. The conducted research is of explorative nature, relying on a critical and speculative design approach. Key aspects and their influence in shaping proactivity were identified.  Insights upon different means of feedback, namely coloured light, motion and sound are discussed in connection with the spatial placement of a proactive artefact and the provided user experience. The notion of gaining versus losing control to an artefact is presented and a reflection on the concept of annoyance as a design material. A proactive system featuring a collection of physical and digital interactive artefacts was created as part of this research. Insights and conclusions are based on conducted interviews after user-testing those artefacts.