Context-oriented systems are systems that observe and handle context information from the environment to guide their own behavior. Engineering such systems represents a complex task not only due to their complexity, but also due to the notion of context. Handling this notion involves tackling several challenges, demanding to system designers a certain knowledge and expertise about this notion. In order to help designers on this engineering process, we propose in this paper a roadmap on context management and a requirements elicitation process. This roadmap aims at sharing with non-expert designers the necessary expertise on context management allowing them to better understand the notion of context and its challenges. The elicitation process aims at guiding these non-expert designers across the roadmap, supporting them in their requirements elicitation process concerning context management. The proposal is presented on a running example that illustrates the approach.