This paper illustrates design work carried out to develop an interactive theater performance. HCI has started to address the challenges of designing interactive performances, as both audience and performers’ experiences are considered and a variety of professional expertise involved. Nevertheless, research has overlooked how such design unfolds in practice, and what role artists play in exploring both the creative opportunities and the challenges associated with interweaving digital technologies. A two-day workshop was conducted to tailor the use of the ChameleonMask, a telepresence technology, within a performance. The analysis highlights the artists’ work to make the mask work while framing, exploring and conceptualizing its use. The discussion outlines the artists’ skills and design expertise, and how they redefine the role of HCI in performance-led research.