The aim of this mixed-method pilot study was to expand the understanding of potential methods to support collaboration between vocational schools and workplaces and to enhance workplace guidance processes. Specifically, we evaluated whether a Cultural-historical Activity theory-based intervention program could have beneficial effects on school-workplace collaboration and on the individual-level competencies of the teachers and workplace personnel. Our results indicate that the change workshop provides a potential mechanism for enhancing personal competencies such as self-efficacy and for promoting collaboration between schools and workplaces, especially in terms of defining objectives for workplace learning. Our study also highlighted how the change workshop method has the potential to trigger expansive learning, in which school personnel and workplace trainers, through learning actions, can change and create new ways of working together. This study highlights the importance of providing workplaces and educational institutions with opportunities to share experiences and learn how to promote workplace-situated learning together.