Many systems have been developed for creating syntactically annotated corpora. However, they mainly focus on interface usability and hardly pay attention toknowledge sharing among annotators in the task. In order to incorporate the functionality of knowledge sharing, we emphasized the importance of normalizingthe annotation process. As a first step toward knowledge sharing, this paper proposes a method of system initiative annotation in which the system suggests annotators the order of ambiguities to solve. To be more concrete, the system forces annotators to solve ambiguity of constituent structure in a top-down and depth-first manner, and then to solve ambiguity of grammatical category in a bottom-up and breadth-first manner. We implemented the system on top of eBonsai, our annotation tool, and conducted experiments to compare eBonsai and the proposed system in terms of annotation accuracy and efficiency. We found that at least for novice annotators, the proposed system is more efficient while keeping annotation accuracy comparable with eBonsai.