Educational Technologies (EdTech) have changed teaching-learning methodologies, challenging the actors involved in education systems (government, private entities, parents, institution leaders) but especially students and teacher’s skills. During the last decades, the biggest impact has been the implementation of artificial intelligence (AI) in most of the industries innovation, but in education is still a concept with mixed opinions. Then, EdTech designers have the liability to understand the technology, the system purposes of the system, and especially the user involve on the project. The research approach was inspired by the experience obtained on CHECK project, an AI technology experimental work sponsored by the Alta Scuola Politecnica and IBM.