Disclosed is a network management system that provides an interface to enable diagnostics and troubleshoot of a remotely managed multi-site network. Some embodiments provide a natural language interface, while other embodiments provide a chatbot type interface that communicates with a technician via traditional text information on a display screen. The diagnostic and troubleshooting capabilities search a central data store that receives device property information from each site of the multi-site network. Based on devices or users that match portions of the entity, queries to the data store are initiated to obtain additional data on the devices. A response to the query is then provided based on the properties of the devices.