The Digital Transformation process, especially in vocational high school, is highly complex and should be understood by scholars. We use seven stages of soft systems methodology to contribute to a deeper understanding of The Digital Transformation process, especially in vocational high school as a policy issue. The research was done in Vocational Highschool 2 Medan. The method used was an exploratory study. In-depth interviews were done to gather data. The main interviewees were all stakeholders (principal, teachers, students, alumni, and parents) related to the process. The outcomes showed the actors involved and the obstacles experienced by the actors in transforming the existing condition into the digital one. The paper proposed a digital transformation model in vocational high schools using the soft system approach. The research limitation was due to the limited research object used, so broader research using this approach is urgent to understand the model.