This paper deals with the design problems in healthcare information systems on how to adapt to dynamic factors and diversities so as to reach the interoperability between healthcare actors. Those dynamic factors and diversities are caused by, for example, constant suggestions from users, changes in the applied technologies, and after-learning related stepwise progresses. We suggest applying Web services technology, especially the idea of Semantic Web to tackle the problem of diversity in healthcare branch. In order to tackle the problem of dynamic changes during the design process, we suggest an evolutionary design methodology based upon an organic development metaphor – embryonic prototyping approach (EmA). We demonstrate our idea by the project IMIS that is to design a semantic Web service for the diabetic healthcare.