This study had three primary goals. First, it aimed to craft an intervention program centered around collaborative learning enabled by Padlet. Second, it aimed to gauge the perceptions of health management students regarding this intervention and how it affected their collaborative learning experiences. Additionally, the third objective of the study aimed to investigate how students’ flexible thinking within the learning process might shape their perceptions of the advantages derived from this instructional activity within the domain of online collaborative learning. Data for the analysis were gathered from 100 Israeli undergraduate students by two measurements: Flexible thinking in learning and Student perceptions of collaborative learning via Padlet. The intervention program included several stages. First, the students discussed the pedagogic objective of using Padlet. In the second stage, the students were presented with ill-structured problems related to the course content. Each group had to choose one problem and analyze it from three perspectives discussed in the course—healthcare provider, patient, and organization. Next, the students presented and explained their solutions employing the shared knowledge base. The final work was presented in different formats using various technologies. The PLS-SEM analysis has corroborated our hypothesis that students’ flexible thinking might positively contribute to their perception of Padlet utilization. According to the empirical model, in general, students who perceived themselves as more flexible were found more receptive to utilizing the proposed technological tool (Padlet) and hence tended to appreciate its function as a collaborative learning platform enabler. This study mainly underscores the important role flexible thinking plays in motivating managers and medical professionals to embrace innovative technologies or methods for teamwork, that could enable them to weigh arguments, seek alternative solutions to authentic problems, and adjust their approaches effectively and collaboratively as new challenges emerge.