(1) Background: The article proposes a methodical procedure for assessing the risk of implementing the diversification strategy of an industrial enterprise based on of management information technologies. The result of which was the improvement of the solution of practical tasks of the diversification strategy with the help of economic and statistical modeling; (2) Methods: the article proposes a methodology for assessing the risk of implementing a diversification strategy, which is based on modeling a portfolio of strategies using economic and statistical indicators: mathematical expectation; dispersions; covariances; (3) Results: As a result of the approbation of the methodical approach, the issue of optimization of complex diversification plans of enterprises in the conditions of the implementation of information technologies was considered. This approach is based on achieving such a structure of diversification of the enterprise, when the expected efficiency will be the maximum possible, and the expected risk will be the lowest. The solution to this problem was realized on the example of product diversification, when the enterprise decides to open the production of several heterogeneous goods; (4) Conclusions: It was concluded that combinations of key success factors distinguish one segment from another, then there are always factors that are part of several or many areas. The obtained calculations showed the possibility of using this methodical approach when assessing the risk of implementing a diversification strategy in the conditions of the introduction of information technologies. The possibility of its use in the context of justifying the choice of a variant of a diversified production portfolio of an enterprise organized on the basis of management information technologies is considered.
