Abstract. Similar to any investment decision, implementation of e-Work solutions requires a comprehensive rationalization from various perspectives, especially economy, productivity and sustainability. Considering e-Work, in general terms, as a sort of technology encapsulation (Nof, 2003 and2007a), this chapter focuses on the prioritization of e-Work implementation plans. Realization of e-Work solutions depends highly on the demonstration of its inherent benefits to individual, networked e-Systems, and the users. The strategic requirements of an e-System are considered as a starting point to identify proper e-Work processes and solutions. As discussed earlier in this book, in line with the emergence of e-Systems, various e-Criteria are continuously evolving, which must be incorporated in the rationalization process as key performance indicators (e.g., reconfigurability and reusability of software and processes). Therefore, a robust framework is indeed required to support rationalization of e-Work implementation projects based on multiple (and somehow conflicting) e-Criteria.In this chapter, basic operational strategies and traditional economic rationalization procedures are first reviewed. It is shown that traditional procedures cannot sufficiently address some emerging aspects of e-Work and disregard strategic benefits of technology. Several scenarios for production of goods and services are then analyzed in the form of value chains, corporative level strategy, business units strategies, and functional strategic planning to determine the operational strategies. Process specification is performed through Value Stream Maps (VSM) for each enterprise to achieve a cross-company operational specification. e-Work alternatives can then be evaluated through defining and prioritizing the implementation plans. Technology evaluation models are introduced for evaluating of the results. Such models conform the implementation plans for different e-Work alternatives. The goal is to maximize the benefits of enterprises and enhance the specification of eWork processes and technologies through prioritizing the enterprise plans for research and development. Finally, a comprehensive Multi-Criteria DecisionMaking (MCDM) framework, based on Analytic Hierarchy Process (AHP) and Data Envelopment Analysis (DEA), is introduced for evaluation of e-Work alternatives based on multiple e-Criteria.