"When the Real Estate Clock hits the evening hours and markets are experiencing a decline in vacancy rates, it is time for owners and developers to look at a more efficient and sometimes """"sexy"""" way of proposing their stock to the market. A number of different factors can drive tenants to the Asset. Some are intrinsic like a more visible or better served location; some are immediately known - old good tools - like price and incentives strategies, or marketing and communications capabilities of the agency team. Some others may be less evident from the beginning but can do the difference once the potential client has considered the building and is in the process of comparing the market offers. That is the case of a clever repositioning of the building to better cope with a competitive market and new Corporate and End-Users needs. This paper investigates the importance of technical and design issues for real estate portfolio managers and also for office occupiers from various organizations in Milan and Rome. The research focuses on existing single and multi-tenancy buildings located in the city centre and peripheral areas. The research is based on direct professional experiences, interviews and questionnaires gathered in 2010 between organizations that were looking for new office space to ask them about their attitude towards several issues. Informal meetings and interviews were also conducted with real estate agents and asset manager of some of the primarily industry sector leaders. This paper may therefore suggest a more efficient approach to reposition existing stock, market empty assets and retain corporate users also once new properties will be available."