Collaborative exploration is one of the essential factors in advanced intellectual activities such as group work in project-based learning (PBL) and research work. Skillful sharing of the intentions of search and their results is quite important to enable collaborative exploration to be smoothly conducted. However, such sharing is usually difficult for members since they often face difficulties in expressing search intentions into queries and suffer from the troublesome activity of page selection. Such problems become more serious for novices. In particular, it is important but difficult to sufficiently understand the differences between search intentions and actual browsing situations. Moreover, there is often insufficient mutual understanding of differences in search policies between members of collaborative exploration since they tend to superficially confirm the search results. This research was aimed at developing novel support to cultivate the consideration skill of search strategy focusing on the novices' understanding of search contexts. This paper mainly describes the framework of support methods and provides a system overview. This paper also discusses the basic effectiveness and characteristics of our methods based on the results obtained from an experiment.