The involvement of Stakeholders in requirement collection of software projects is essential, and that is evident in the diverse methodologies available that emphasise stakeholder collaboration. However these processes scarcely provide further understanding of the social interaction, and its effect into forming collaboration had not been sufficiently addressed by software development research. It is challenging to identify dominating factors that affect collaboration due to the complexity of stakeholder interaction. This thesis addresses such a challenge. It discusses a systems approach to the evaluation of stakeholder collaboration within requirement collection of software projects. A generic approach has been developed to contribute to our understanding of the problem and support stakeholders’ collaborative involvement. Based on understanding the nature of collaboration between stakeholders in requirement collection, and the concept of perception and its contribution into forming collaboration, the EStaC (Evaluation of Stakeholder Collaboration) approach is developed. EStaC is presented here to describe an integration of multi-methodologies that supports capturing stakeholders' perspectives, and therefore systemically it captures the essence of collaboration within its context. EStaC contributes to the crucial phase of requirement collection with the ultimate objective of extending it to include means of improvement of stakeholder collaboration. It promotes the development of two modes of analysis, the design and diagnosis, which both involves using the principles of the Viable System Model. The novelty of this work is specifically considered with the development of the EStaC approach because unlike other approaches, it focuses on the social act of interaction from a stakeholders viewpoint, by applying systemic strategies and cybernetic driven principles with concepts of fourth generation evaluation. The research recognises evaluation of stakeholder collaboration as an important aspect in the requirement collection process in any software development. It concludes and supports the incorporation of such activities throughout various phases of requirement collection.