With this lecture we are sharing our practical findings in the eSangathan Project, interpreted from the theoretical perspectives of Inquiring Communities and Collaborative Working Environment (CWE). We start by investigating the use of IT and CWE in support of Inquiring Communities among seniors working to create social innovations. We identify five different forms of Inquiring Communities: the Realistic, the Analytic, the Idealistic, the Dialectic and the Pragmatic. These communities we take to be basic and essential for communication and sharing of knowledge among human beings. As there are not very much evidence on the CWE support of all these five communities we use theories on Knowledge Management as a stepping stone, because there are substantial evidence of support for Knowledge Management by CWE, even though Knowledge Management lacks a sound theoretical foundation. As Knowledge Management only can illustrate the Realistic, the Analytic and the Idealistic types of Inquiring Communities we see a lack of support by CWEs for the most crucial aspects of communication and knowledge sharing, that among differences of opinion as in the Dialectical and Pragmatic communities. Finally we explicate findings on good practice in CWE as we have experienced them in the eSangathan project together with some important dilemmas for further investigations.