Encouraging individuals to adopt healthier behaviors, routines, and ways of living often requires a structured process built on shared goals and cooperation—this is the essence of a Behavior Change Intervention (BCI). A variety of technological tools can be used to deliver BCIs, ranging from mobile applications to embodied artificial agents like, e.g., robots; however, comparative analyses of how users perceive the usability of these different systems are still lacking. This paper presents a preliminary investigation into users’ preferences regarding different technologies as tools for promoting behavioral change. We evaluate the perceived potential of these technologies, with particular focus on usability and its relationship to users’ familiarity with them.