Over 350 national and international delegates at the 2nd e-Skills Summit and the International Telecommunication Union (ITU) Global ICT Forum on Human Capital Development have agreed that the e-skilling agenda in South Africa is making a "profound difference" but still not sufficient to build a capable developmental state. The delegates suggested that for positive impact in addressing inequality, poverty and joblessness--a new approach to e-skilling was needed. It was generally agreed that some "soft" skills were needed to help people successfully apply e-skills to benefit their everyday life. These skills were identified as "e-astuteness" and "e-social astuteness". The objective of this study is to provide the conceptual clarity of these two terms, i.e. the general aim of this study is a theory building around these two concepts. The findings of this study confirmed that concepts of e-astuteness and e-social astuteness, together with e-skills, can be useful in addressing the South Africa's major developmental agenda as articulated in the national developmental strategies.