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Objective behavioral personality measures are an alternative to traditional self-report personality assessment and overcome some of the difficulties traditional assessment has. This paper presents two studies to validate two measures of risk propensity. In Study 1, 1,325 applicants for an ab initio air-traffic control training program were assessed using the Roulette Test (RT) and the Crossing the Street Test (CtST). Convergent as well as criterion validity were tested using the guessing tendency demonstrated by participants in a multiple-choice test. Once the effect of general cognitive ability was leveled out, results showed the predictive capacity of both tests. Study 2 replicated the previous study: 127 3rd-year psychology students were assessed using the RT. Results showed that the test had an even higher predictive validity of the Guessing Tendency (GT) revealed in a multiple-choice test. The usefulness for personnel recruitment processes and other assessment contexts is emphasized as are future trends of objective personality assessment.