Much of the work that explores and studies the indicators for ICT readiness focuses on the economical factors joint by a sufficient level of education, as the driving force for the wide spread of these technologies. It has been argued that the diffusion rate is in most cases proportional to the growth of the income. Despite of the relatively high level of the human development index in most of the Central and Eastern European countries including the former Soviet republics, the degree of connectivity and Internet use demonstrates large discrepancies. Ten of them with the highest GDP have joined the EU and have much higher ICT diffusion compared to the others. Interestingly enough some have achieved the same rate of ICT diffusion despite significantly lower level of wealth. Sharing their positive experience with the CEE countries that are lagging behind with respect to ICT diffusion could possibly reduce and finally diminish the digital divide. The experience with ICT diffusion in the CEE countries is explored and a model for identifying the predominant factors was developed in order to identify those that have achieved high level of connectivity and ICT use, yet with limited resources and depending heavily upon the knowledge of its people. Estonia has expressed very high inclination and enthusiasm towards experimenting with and adopting the contemporary technologies. One of the decisive factors for establishment and development of the information society have been the IT-program for developing e-services, accompanied with creating access for all the citizens. The lessons learned from Estonia�s experience served as guidance in developing the three pilot projects implemented in Armenia and Macedonia. The primary goal was to provide means of how to possibly overcome the debilitating ignorance that spans from an ordinary citizen to a high level decision maker, in understanding the width, the depth, the profoundness, and the power of the ICT.