The concept of socio-technical self-descriptions can be employed to run CSCW-projects where several perspectives have to be integrated in a process of decision making. The decisions are related to technical as well as organizational structures and their interplay. Current approaches do not sufficiently match the challenge to facilitate the communication processes during CSCW-projects. The alignment of software-development and configuration on the one hand with organizational changes and regulations on the other hand need specific forms of documentation which can be considered as a kind of self-description. In this paper we explain how semi-structured diagrams can fulfill these requirements, if they are embedded in appropriately facilitated communication processes. We provide guidelines and recommendations which were derived from several case studies and were refined during a project which planned to support the cooperation between truck drivers and dispatches by using mobile pocketPCs.