Artificial Intelligence (AI) tools are currently and consistently increasing their popularity not only in daily life tasks but also in professional environments. This novel reality is also relevant in the academic world, where undergraduates employ these tools to assist their learning process. The primary goal of the present work is to evaluate the best way to interact with the main AI tools available to the general public for use as assistants in the teaching–learning process. Among all the available tools, ChatGPT has become one of the most widely used due to its simple interface and the availability of a powerful free version. To assess the suitability of these tools in the field of technical drawing teaching, a question bank with different levels of complexity is created, covering content related to representation systems and applicable standards in the Graphic Expression subjects taught in engineering degrees. With the help of specially developed rubrics, an initial evaluation is carried out by the teaching team to obtain unbiased feedback. Subsequently, students solve the proposed bank exercises with the help of AI, recording all interactions made with it and providing a critical assessment of the AI's responses. With all this information, a detailed analysis is conducted to clarify which types of interactions yield the best results from a technical perspective. Based on this analysis, various recommendations are drafted to optimize the interaction between students and AI tools in the teaching–learning processes. Additionally, recommendations for the critical and responsible use of these tools are incorporated into the course content.