Effective design and implementation of any IT Optimization process relies on critical technical and business insights about IT environment. The essential information, which relates to hardware and software assets, is often in collective possession of the infrastructure and application specialists. In this paper, we describe the Knowledge Harvesting & Information Synthesis System (KHISS), which engages enterprise online communities to capture the information required for IT optimization activities. We describe our experience in deploying KHISS principles to manage enterprise IT infrastructure and application portfolio, as a first step in on-Cloud migration - a large business transformation activity. We discuss the challenges in attracting and maintaining enterprise online communities, as well as in assuring the quality of knowledge collected through this collaborative mechanism to guide the strategic decisions about enterprise IT environment. © 2011 IEEE.