This practitioner paper explores the background of the development of two separate information systems. The first a case study where a SME was able to commission the design and implementation of an information system that offered a solution to restraints on the growth of the business, and a second case study of an SME, whilst unable to articulate the requirements for an Information system, with the support of a patient programmer, was able to commission a system that was developed, grew, and was sustained, over a ten year period. The paper explores the ideas of how both commissioners and developers can negotiate to a point of mutual understanding benefiting all stakeholders of the system and, as a result of learning from practice, The discussion point of this paper is a reflection on theory from the perspective of the practitioner.