The paper articulates the problem of modeling management decision-making process in new digital reality: decision-making under uncertainty, volatile environment, huge amount of data to be accounted, objective analytical risk attitude. The proposed solution includes critical selection of risk and uncertainty management tools aimed at improvement quality of management decision-making information support in the sustainable development context (on the example of construction projects). The aim of research is the development of the new "digital" approach to the process of reducing uncertainty when decision making in highly risk projects, including the process model and toolkit. Methodology is based on logical analysis and synthesis, decomposition, qualitative analysis of the relevant literature and primary data (top management informal interviews, targeted sample), comparative and regression analysis, time series analysis, mathematical statistics and simulation modelling based on nine sets of design estimation paperwork and turnover-balance sheets. The contribution into the existing knowledge includes substantiating the correlation of the terms of the digital decision-making and simulation modeling tools in high-risk projects management under insufficient statistical data and their mutual interaction. Also, advisability of formalization of the decisionmaking method based on unprocessed design estimates is justified, and appropriate methods for sustainable decision-making information support are selected. The approbation demonstrated practical significance and economic effectiveness of developed approach; experiment was carried out on the base of «RSU -6» LLC's projects (Tchaikovsky, Perm region).