An employee of a large organization sends a human-readable document such as an email or text message to another employee of the organization to inform the other employee of a change in availability. A trained machine-learning model extracts, from the human-readable document, data used by a leave management system (LMS) to formalize and memorialize the leave request. For example, the employee name, manager name, date leave begins, date leave ends, reason for the leave request, or any suitable combination thereof may be determined by the machine-learning model based on the human-readable document. The extracted data is provided to the LMS and the leave request is created.