The introduction of innovative digital tools for supporting manufacturing processes has far-reaching effects at an organizational and individual level due to the development of Industry 4.0. The FACTS4WORKERS project funded by H2020, i.e., Worker-Centric Workplaces in Smart Factories, aims to develop user-centered assistance systems in order to demonstrate their impact and applicability at the shop floor. To achieve this, understanding how to develop such tools is as important as assessing if advantages can be derived from the ICT system created. This study introduces the technology of a workplace solution linked to the industrial challenge of self-learning manufacturing workplaces. Subsequently, a two-step approach to evaluate the presented system is discussed, consisting of the one used in FACTS4WORKERS and the one used in the “Heuristics for Industry 4.0” project. Both approaches and the use case are introduced as a base for presenting the comparison of the results collected in this paper. The comparison of the results for the presented use case is extended with the results for the rest of the FACTS4WORKERS use cases and with future work in the framework.