The link connecting two constituents in a syntactic dependency relation has been a key measure of interest in the studies of syntax. This include the positioning of a head word in regards to its dependent or the head directionality. The direction of the link connecting both constituents is a familiar topic in syntax through a phrase structure perspective. However, it is yet to be explored using dependency approach, particularly in Indonesian language. This study uses a large-scale corpus of Indonesian language in written and spoken manner. The preliminary findings exhibit that there are particular conditions in which head-initial dependency direction is preferred over head-final relation. The analysis also indicates a preference to position the head before its dependent albeit producing a longer dependency distance. Overall evaluation shows that aside to the minimization of dependency distance, Indonesian speakers might choose a certain position of the head to better facilitate cognitive demands and reduce the process happening in the working memory.