Recently, in the commercial and entertainment sectors, we have seen increasing interest in incorporating chatbots into websites and apps, in order to assist customers and clients. In the academic area, chatbots are useful to provide some guidance and information about courses, admission processes and procedures, study programs, and scholarly services. However, these virtual assistants have limited mechanisms to suitably help the teaching and learning process, considering that these mechanisms should be advantageous for all the people involved. In this article, we design a model for developing a chatbot that serves as an extra-school tool to carry out academic and administrative tasks and facilitate communication between middle-school students and academic staff (e.g., teachers, social workers, psychologists, and pedagogues). Our approach is designed to help less tech-savvy people by offering them a familiar environment, using a conversational agent to ease and guide their interactions. The proposed model has been validated by implementing a multi-platform chatbot that provides both textual-based and voice-based communications and uses state-of-the-art technology. The chatbot has been tested with the help of students and teachers from a Mexican middle school, and the evaluation results show that our prototype obtained positive usability and user experience endorsements from such end-users.