In this paper, we present a problem structuring method in business and IT analysis illustrated with an example. The project describes an IT consulting case done for a Swiss medical society faced with a problem of change management and digital transformation. We show business analysis techniques of modelling actors’ behaviour, motivation, and information exchanged between them. We model business and IT services and structure case information in order to design a solution to the problem and its implementation requirements. We highlight how accommodation of different viewpoints enables business and IT alignment and removes hindrances to innovation.