In a densely populated city like New York City (NYC), more than 14 thousand buildings are mandated for the façade safety inspection program to ensure public safety. Current inspection process relies on visual inspection by certified inspectors. Photos and sketches are adopted to document the findings during each inspection. Existing construction code from city departments provides the general information of a façade safety program, while a generic checklist that an inspector can follow for each exterior enclosure type is missing. The existing way of capturing building data and defects are ineffective for understanding and not sufficient to provide a holistic view of the façade condition for the review process. This paper provides details and results of three shadowing works conducted with façade inspectors to capture the workflow that façade inspectors follow on different exterior enclosure types. The shadowing results were analyzed to examine the information inspectors collect during the inspection for each component and defect type. Initial findings, presented in this paper, provide evidence for the need for streamlining the existing façade inspection process with an approach that could guide the data collection and decision-making and enable the collection and identification of such information completely and accurately.