The object of the present study is to propose a technologically based method for developing Regulation of Cognition (RC) among pre-service teachers in a pedagogical problem context. The research intervention was carried out by two groups during a Teaching Training Workshop, based on the IMPROVE instructional method, which was implemented in the Learning Management System (LMS). The first group (N = 53) investigated the pedagogical problems with "dual perspectives" (teacher and learner), and the other group (N = 47) analyzed the same problems from a teacher perspective only. The triangulated research design provided three sets of data of RC (e.g., statements on Metacognitive Awareness Inventory, Educational Data Mining, and observations on actual teaching). The results were indicative of the advantage that was obtained by the dual perspective group (LMS+2P), which has manifested in most components of RC, as compared with the single-based intervention (LMS+1P).