Purpose: The purpose of the study is to produce design guidelines based on insights from both practice and theory that will enable teachers and educational developers to execute the design, implementation and evaluation of their work-related learning arrangements with stakeholders involved. Design/methodology/approach: The first study reported in this paper can be characterised as an exploratory design study. The second and third study can be described as design-oriented research. Findings: The case studies showed that to realize work related learning arrangements mutual understanding between stakeholders is needed to decide what has to be learned by the students and to create learning situations that have a high similarity with real working situations. Research limitations/implications: The ultimate evaluation question whether students indeed show high levels of learning outcomes on the levels of the framework when they followed work-related learning arrangements that are arranged according to the design guidelines, fall out of the scope of this paper. Practical implications: Factors that influence the intended and implemented design of work related arrangements are derived from practical and theoretical insights. Design guidelines to influence these factors in a positive direction are formulated, based on these insights. For the expected learning outcomes a dynamic framework is developed. Social implications: Work related learning arrangements are still rare in higher education and practical experience is generally only gained during short periods of internships. So the finding that learning by experience and social interaction and learning by theory and reflection should be combined in joint work related learning arrangements to obtain the most impact on the ability to transfer, will not immediately become custom. Originality/value: Teachers, educational developers and stakeholders who are involved in developing the design, implementation and evaluation of their joint work-related learning arrangements will find evidence based design guidelines and a framework to assess learning outcomes. The theoretical insights are based on a multidisciplinary combination of workplace learning theories, educational science and innovation management theory. (Contains 3 figures and 1 table.)