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The article presents the results of an empirical study about the correlation between such problem solving components as dialectic thinking, problematization, and (adaptive situational problem solving in) meta-situation-transformative solutions of preschool children. The methodological basis for the study is the structural-dialectic approach (N. E.Veraksa) as well as work on dialectic and post-formal thinking (P. Arlin, M. Basseches). The paper describes for the first time the author’s technique for the diagnosis of dialectic thinking “What could the other way around be?” and the results of testing the method “Questions about picture with objects” (Bernice Lai-Ting Yan; P. Arlin) with preschoolers. We also used V. T. Kudryavtsev’s method “Bunny”, which is aimed at measuring the ability of a preschooler to turn a selection task into a transformation task. The study involved 83 children of preschool age (4-6 years) from the following kindergartens in Moscow: «Lesovichok» (34 respondents; program “From Birth to School”); “Fox” (33 respondents; the experimental program “Transformation”); kindergarten №1511 (16 respondents; the program “Development”). The key results were that we found significant positive correlation between such parameters as the dialectical thinking actions “Transformation” and “Shift Alternatives”, questioning, and (adaptive solutions to problematic) meta-situation-transformative solutions of situations. The article also describes in detail the results of diagnosis by each of the methods, which indicate children’s significant difficulties when making oppositions between objects and events, and asking questions that allow them to make a conclusion about the necessity of paying attention to the aforementioned components of the mechanism of creative thinking within the educational process.