While typical academic skills such as research and writing are commonly monitored in Higher Education, generic skills such as teamwork, critical thinking or communication receive less attention. This is problematic in light of discussions on students’ further career development. It is often said that active learning environments facilitate the training of such skills. Having a tool to monitor skills progression is an important prerequisite to properly test such claims. At Maastricht University, we developed a self-assessment tool to raise awareness about skills required to take full advantage of the active learning environment, and to initiate self-reflection on the side of students. While the current tool achieves these objectives, it is less suited as an instrument for measuring skills development. In this article, we propose a re-developed self-assessment tool and test its merits through a quasi-experimental study. A group of sixty-two students was asked to complete both the old and new version of the tool. Students and mentors were subsequently asked to evaluate which score represents students’ skills level best. We evaluate if the new self-assessment tool provides a better insight into students’ generic skills development in an active learning environment.