As a user is drafting an electronic document (e.g., a word processing document, spreadsheet, etc.), the user may enter a predefined string of characters that represents a placeholder for information which is to be inserted into the document. A computerized system recognizes the predefined string of characters and, in response, automatically opens a messaging window that permits the user to request the information from one or more recipients. The message may include a portion of the electronic document surrounding the predefined string of characters to provide context for the recipients. A recipient can edit the context provided in the message to provide the requested information and transmit the message back to the user. If the user approves the edit made by the recipient, the computerized system may be configured to automatically integrate the edit into the electronic document.