The research aims to study the factors characterizing the sustainable development of an enterprise. Nowadays, the activity of an economic entity is characterized by several indicators that reflect the enterprise’s profitability and make it possible to make informed management decisions. The research aims to characterize the development of railway company management practices for insolvency risk analysis. The research methodology is based on a comparative sampling survey, economic-analytical, and expert methods. The authors studied the comparative description of controlling, provided a rationale for the importance of controlling tools for making effective management decisions, and offered a practical understanding of the use of controlling tools at each stage of management decision-making. The use of controlling is crucial for enhancing the validity, efficiency, and analytical quality of information regarding an enterprise’s activities. This aligns with current corporate governance standards, increases accountability among performers, improves the management system, and boosts the profitability of railway transport enterprises.