Methods are provided in which a computing device obtains, from one or more disparate data sources, inventory data of a plurality of network resources in a plurality of domains of an enterprise network. The inventory data includes configuration information of the enterprise network. The method further includes the computing device selecting one or more contextual insights that apply to the inventory data of the enterprise network from contextual information related to one or more networks and configuration of the one or more networks and generating one or more contextual guides specific to one or more affected network resources of the enterprise network based on the one or more contextual insights.