Computer Diagrams are the communication mechanism among the different stakeholders of the software development lifecycle. While they are though at school, and promoted to be used by students for current and future projects, we still do not see full adoption in real life context. The literature reviewed points out some reasons related to this issue and propose some solutions, but still the problem persist. In this paper, we present our findings of three years of research at the University while working with senior students on real-life projects. Different methodologies were used as an iterative process, improving the quality of the results year by year. We present the lesson learned including guidelines on how to facilitate novice engineers to adopt diagrams and produce them with high quality standards. The proposal is validated with a real life case study.