E-government is now a worldwide and complex phenomenon. A dominant view of how it should be evaluated focuses on asessing both e-government evolution and use. Questions about the purposes and contributions of e-government to societal improvement are being excluded from evaluation. In this chapter a case study of Colombia is used to gain insights into the challenges faced by evaluators. With these insights and using systems thinking as a body of knowledge, three (3) conceptual patterns of practice are defined to help stakeholders engage with evaluation activities and positively improve the influence of e-government in society