A content server can extend enterprise content management to a leading system in an efficient, automated, and seamless manner by leveraging the permission information provided by the leading system. The content server can sync the permission information with the leading system, evaluate user-manager relations, role-based rule definitions, and user-group associations defined in the leading system, and determine and/or update role memberships for workspaces created in the content server for users in the leading systems. In this way, even though the content server and the leading system have very different types of roles and permission models, the content server can evaluate complex relationships and role-based rules and intelligently, correctly, and quickly assign the right people to the right roles in the right workspaces in the content server.