The city area is dense with business activities, public amenities, transport hubs and high-skilled people. Corporations prefer to be located in the city area to gain benefits from the location. However, annoyance occurs because of the real estate decisions of organisations as they neglect urban planning and context and results in inefficient, inflexible, closed and leads to the mono-function problems. The research aims to examine the important variables that encourage the interaction between the corporate office building and the city from the users’ perspectives and the designer’s ideas. The research is divided into two parts, which are the theoretical study and empirical research. A literature review is conducted in the first part to establish a theoretical framework, which will be the guideline for empirical research. Empirical research is carried out based on the three case studies: CIRCL, The Edge and Groot Handelsgebouw. The methods for case studies are documental study, semistructured interviews, user surveys, and direct observation on the real estate objects and people’s behaviour in public space. Results from the theoretical study and empirical research are gathered to conduct a cross-case analysis. The findings of the research determine eight essential variables to enhance the interaction between corporate office building and the city from the user’s perceptions and the designer’s intentions. The eight variables are accessibility, flexibility, function and activity, inclusiveness, aesthetics, openness and transparency, human scale, and sustainability. The findings of the research benefit the three fields. Firstly, the research can be used as a guideline of the corporate real estate development by the real estate manager. Secondly, the research provides knowledge of factors for the interaction in the design field. Lastly, the findings of the research can be included in the urban development plan of the municipalities. corporations and cities, corporate real estate management, urban area development, interaction, CIRCL, The Edge, Groot Handelsgebouw, accessibility, flexibility, function and activity, inclusiveness, aesthetics, openness and transparency, human scale, sustainability.