Architectural works are mainly composed of a container designed to have a function in itself (e.g. a triumphal arch) or to have one or more functions. It is difficult to separate a piece of architecture from the function it has been designed for and at the same time, it is not correct to isolate it from its geographical context in which it was placed or from the historical and cultural context that produced it and modified it. Besides having unique characteristics, such as its location, shape and function, a piece of architecture holds expressive content, the capacity of which varies in relation to its context, age, or to the desires of the designer or the client. When is it necessary to identify the expressive content of an architectural work? When does this dictate the planning decision on whether to demolish or preserve a part of it? If a piece of architecture shows issues of preservation, whether these are caused by natural degradation of human neglect or not, it is possible to tackle the described situation with various approaches and proposing different design solutions. These solutions could vary massively from one to the other: from the complete demolition of the building that is no longer considered useful or significant, to its utmost rigorous preservation and of its function also. The choice to preserve a building (meaning a voluntary act to slow the degradation, which every building is affected by with time) is based on the recognition of one or more significant aspects of its expressive content, which we may refer to as purpose. There can be multiple meanings, even if they may not occur at the same time: social, historic, cultural, religious, political and last but not least, economic. All meanings can be of certain value for an individual or for a small or large community. The more evident and shared by different involved parties (not only designers, but also managers, clients, etc.) these meanings are, the more felt and shared is the need to preserve the building. However, not all purposes of a piece of architecture are instantly noticeable, as not all of them are physical elements (shapes, constructive elements, materials, colors, spaces, etc.). In some cases, an architectural work evokes specific values that are not easily expressed in practical terms. Therefore, if physical preservation can preserve the expressive content of an architectural work, it cannot always preserve the values this work evokes. How do we recognize the expressive content and the values borne by a piece of architecture or a place?