Abstract Context: In Germany, schools are responsible for the overall organisation of career guidance (Kultusministerkonferenz (KMK), 2017). This means that schools must make decisions regarding content and didactics, as well as personnel and organization, to develop and implement a career guidance concept (Driesel-Lange et al., 2020). This raises the question of how schools can be supported in the complex task of realizing individual support within the concept. Klein et al. (2024) define seven areas of development (CG team, CG concept, school management, personnel, network/cooperation, infrastructure and implementation) that schools should focus on to further develop quality-led individualized career guidance. Subsequently, an initial working method, based on a digital question tool, is proposed. It is essentially founded on identifying possible next development goals based on a status quo (of the seven areas) and developing these in a structured manner. Approach: The research and development project “DIGIBO Best! Developing and managing career guidance at school with digital tools” aims to create a data-based concept for further development of school-specific career guidance. Based on the design-based research approach (Euler, 2014), this concept is being developed in collaboration with 20 secondary schools. In addition to prepare a scientifically sound strategy for school practice, the assumptions and working methods inherent in the Klein et al. model (2024) will be reviewed, modified and consolidated. Interventions at the participating schools form the basis for the review and continuation of the approach. In terms of the individual school development of career guidance, the schools contribute their specific topics and concerns. The intervention begins with an initial workshop in which a SWOT analysis and the invented question tool are used to identify the seven areas named for career guidance in the model of Klein et al. (2024). At the same time, the strengths, weaknesses and development potential of the individual school are to be linked to this. This article aims to present the theoretical model of the question tool and the results of the first series of workshops. Findings: The first workshop phase with sixteen schools revealed their individuality. The development areas are characterized differently, and their importance is weighted variably. Schools link the evaluated development-critical areas with various topics that should be worked on next. There are also common themes across several schools that currently pose challenges for schools. Conclusions: It is clear from both the project design and the initial results that career guidance must be viewed at the individual school level. It is noticeable here that the academic discourse (career guidance as a school-wide task, necessity of individualisation) is reflected in school practice.