In my practitioner experiences in developing management systems, I have to understand the external and internal context of the organizations. I briefly summarize my methodological approach and I present the features of the workshops that drive my projects. In particular, I describe my experiences of workshops in the form of interviews, applied to develop the analysis of the context and, recently to explore the topics of work systems and sustainability. The results of these workshops highlight the broad network of relationships among context issues, technologies and organization systems and the difficulties in transferring this high level of interdependence and complexity in the organizational structures. Learning from these experiences I pose some reflection on job organization, job classification and on the role of relationships and behaviors in managing the present digital transformations