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In this paper, we present a new approach for the optimal experimental design problem of generating diagnostic choice tasks, where the respondent's decision strategy can be unambiguously deduced from the observed choice. In this new approach, we applied a genetic algorithm that creates a one-to-one correspondence between a set of predefined decision strategies and the alternatives of the choice task; it also manipulates the characteristics of the choice tasks. In addition, this new approach takes into account the measurement errors that can occur when the preferences of the decision makers are being measured. The proposed genetic algorithm is capable of generating diagnostic choice tasks even when the search space of possible choice tasks is very large. As proof-of-concept, we used this novel approach to generate respondent-specific choice tasks with either low or high context-based complexity that we operationalize by the similarity of alternatives and the conflict between alternatives. We find in an experiment that an increase in the similarity of the alternatives and an increase in the number of conflicts within the choice task lead to an increased use of non-compensatory strategies and a decreased use of compensatory decision strategies. In contrast, the size of the choice tasks, measured by the number of attributes and alternatives, only weakly influences the strategy selection
