This paper presents the generation of a Q-set for two Q studies investigating the perspectives of (1) patients with multiple sclerosis and (2) their healthcare professionals on the use of wearable technology. It describes the adopted Q methodology and how it was applied in different phases. The concourse is derived from the relevant literature, based on the unified theory of acceptance and use of technology (UTAUT2) model, with privacy as a moderator, and Hofstede’s “Cultural Dimensions” framework, incorporates statements drawn from the concourse following review by experts This is followed by a pilot study involving 4 stakeholders to improve the relevance and quality of the research. A 43-statement Q-sample was developed for the first Q study, and a 32-statement Q-sample was developed for the second Q study. This preliminary study reported the development of a legitimate and reliable concourse in a transparent and comprehensive manner. The lessons learnt from developing the concourse in this study could be beneficial for future research when conducted in a similar digital healthcare context and in the context of MS where individuals often experience symptoms related to vision, sensation, coordination, and movement.