The world’s population is ageing. Older members of society have needs from IT which can be quite specific, reflecting their living arrangements and increased likelihood of suffering from physical and cognitive impairments. So how can businesses offering IT services understand these needs to develop products and services that this demographic group (and their carers) will be willing to adopt? In this paper we outline the process we went through to attempt to answer this question. Because our research involved elderly and (in some cases) disabled trial participants, the process had ethical considerations at the forefront, which on occasion affected the operational processes involved in bringing the trial to life. We describe the various challenges we encountered, where possible how we overcame them (by balancing commercial, stakeholder and participant requirements or by compromising where we could not), and what we learnt for future trials.