A content management system categorizes electronic documents stored in a document storage database. The electronic documents include metadata. The content management system includes a categorization rules database of categorization rules. A recurrent categorization engine takes the rules and applies them to the electronic documents to generate a plurality of category groupings. Each category grouping includes groups based on the applicable rule used to create the grouping. The electronic documents are grouped between the groups. The most balanced dataset of groups is selected to generate a user prompt for further categorization of the electronic documents.