In recent years, because of the development of other areas of Guangzhou, the Huanshi East CBD is facing fierce competition. What’s worse, this CBD has some inborn weakness when compared to the other CBD due to some urban planning mistakes. The first one is that the core of this CBD is divided into two parts by a busy road. The buildings in this area are disconnected. People who want to go to the other sides of the CBD have to walk for a long time or experience the anxiety space under the Huanshi East Road. Besides, people in this area also lack space for recreation and public activities. The aforementioned factors decrease the attractiveness of this CBD. This pose the research question: what can be an appropriate solution for this complicated site? To deal with the huge amount of information of the site efficiently, the application of advanced digital tools and design methodology will become important part of the design exploration. More precisely, combined with the outcome of urban analysis and climate study, a system that refers to the concept of self organizing system / agent based modeling will be built for simulating the function arrangement and initial form – finding. By analyzing the results of these simulations, conclusions can be made with regard to public/private zones, topology and location as well as morphological translations. After that, in the design development stage, with the aid of advanced analysis tools and modeling tools, different aspects of the design such as form and openings can be optimized according to the parameters, context and the programs.