One of the essential prerequisites for improving an organization's capability for flexibility and appropriate, rapid response to the environment is the organization’s ability to internalize specific environmental changes. According to the principle of the necessity of diversity and to strengthen organizational agility, there must be a form of adaptation between the degree of environmental changes and the flexibility of the organizational structure, which emphasizes special attention to the type of organizational structure. Given the turbulent external environment and rapid changes in various fields, organizations tend to implement more flexible structures such as adhocracy. However, any type and level of change within an organization faces resistance and obstacles, some of which are behavioral and others structural. This study seeks to identify, classify, and ultimately prioritize the behavioral and structural barriers to implementing the flexible adhocracy structure in Iran’s shipbuilding industry. In this study, the Delphi method was used to identify barriers, exploratory factor analysis to classify them, and confirmatory factor analysis to prioritize them. The results reveal 17 behavioral barriers classified into 6 main factors and 24 structural barriers classified into 9 main factors. Among the identified barriers, low self-disclosure of human resources was recognized as the most significant behavioral barrier, and insensitivity or low sensitivity to environmental stimuli as the most significant structural barrier.