Self-regulation has become a topic of interest in the educational field as a process that helps the learner improve their learning journey. In this paper, a self-regulation based application that applies the concept of self-assessing learning objectives and, as such, allows for the analysis of the evolution of knowledge acquisition, is presented. This software was developed so that teachers and learners could use it. The Design Thinking methodology was used to develop a user-centric and competitive solution. Furthermore, heuristics and an interview process were conducted to evaluate the applicability of the software in classrooms. This led to a consensus between the interviewed educators regarding the viability of the use of the system, while also contributing to a more humane evaluation and helping with the identification of a learners’ needs. As future work, it’s expected that a set of rules are created to help with the implementation of this software in higher education.