The primary objective of this paper is to present an exploratory study on the different measurements used at different milestones throughout a development project. The paper presents the results of a study, which uses qualitative techniques to investigate the cognitive structures appropriate to the requirements phase and the implementation phase of a software development cycle. The study involved an e-commerce project, and two stakeholder groups, the users and the developers. The results show that measurements between the different phases are not the same, though the motivation behind the choice of these measurements is the same for a stakeholder group. The study also finds that the two groups of stakeholders are very similar in the measurements they choose for evaluating requirements documents, however, the motivation behind their choice of these measurements differ between the stakeholder groups. These results are a contrast to that of the implementation phase. These results, whilst still exploratory, are valuable as they highlight the differences and similarities of not just the stakeholder groups, but more importantly the choice of measurements at the different milestones. As a result of this study, the Software Evaluation Framework has been expanded to consider the many milestones in a development cycle. The result of this will be a framework to guide practitioners as they evaluate, test, review, walkthrough, or inspect the different artifacts that the many milestones deliver.