Document management software are used widely for office paper management and related workflows. However, they have some differences from a flexibility perspective for the needs of workers. Moreover, they also differentiate in their underlying conceptual design. In this paper, a set (eight) of widely used document management systems are chosen from internet reviews [5] [6] and their conceptual models are analysed with meta modeling and flexibility tuning measures. The main objective is to compare these systems by analyzing their human-orientation and flexibility. This analysis provides useful information for organizations especially looking for document management systems which are more workforce centric.