This paper reports on a study commissioned by OceanBrowser Ltd, developers of OB3, a collaborative e-learning application for online study in Higher Education. OB3 is designed to lower barriers of uptake by academic staff and students with low levels of digital literacy, who may also be time-starved or technologically disinclined. It implements rich authoring and collaboration features that require accessibility enhancements, in order to meet the technological needs of people with impairments. Development of these enhancements will be informed by the outcomes of this study. A case study was designed and implemented to qualitatively research how severely impaired professionals used ICTs. Interviews and shadowing of participants provided insights showing that the interaction modes, assistive technology, and/or human assistance implemented to interact with mainstream technologies made these people productive, but did not enhance their work performance. These insights also invite us to consider whether studies and explorations of alternative interaction modes and paradigms need to be undertaken in order to improve performance with productivity tools such as OB3. Through gamification, HCI, and Bridging Design Prototypes, a research agenda is proposed to bring about lively, interactive, and inclusive assistive technologies for improving performance.