In a world that changes very fast, it is necessary that educational models evolve at the same speed and that teachers are increasingly prepared and open to deal with current problems. Tecnológico de Monterrey has implemented the Tec21 Educational Model based on four fundamental pillars: (a) Challenge-Based Learning (CBL); (b) flexibility; (c) trained, inspiring teachers, and (d) memorable, integrated educational experiences. The purpose of this study was to evaluate the results of the implementation of CBL experiences in two engineering areas within the campus, namely, Mechatronics and Biotechnology. In this article, we first present how a group of teachers adopted CBL as a teaching technique, and second, we describe the implementation of flexible education with external training partners using CBL in “FIT” (Flexible Technology, Interactive) courses. We also analyze various ways to assess the impact of digital technology tools like CANVAS, REMIND, ZOOM, and eLUMEN on competencies. The results of this research indicated that students acquire more knowledge in CBL classes; however, the teachers require an adequate training program and must have previously designed proficiency assessment instruments. The testing of various evaluation instruments found that checklists and evaluation rubrics were the most suitable, objective, and transparent in CBL classes, according to the surveys of teachers and students.