Reaction time (RT) is a critical measure of performance, and studying its distribution at the group or individual level provides useful information on the cognitive processes or strategies used to perform a task. In a previous study measuring RT in children and adults asked to compare two successive stimuli (quantities or words), we discovered that the group RT distribution was bimodal, with some subjects responding with a mean RT of around 1100 ms and others with a mean RT of around 500 ms. This bimodal distribution suggested two distinct response strategies, one reactive, the other anticipatory. In the present study, we tested whether subjects’ segregation into fast and slow responders (1) extended to other sequential comparative judgments (2) evolved from age 8 to adulthood, (3) could be linked to anticipation as assessed using computer modeling (4) stemmed from individual-specific strategies amenable to instruction. To test the first three predictions, we conducted a distributional and theoretical analysis of the RT of 158 subjects tested earlier using four different sequential comparative judgment tasks (numerosity, phonological, multiplication, subtraction). Group RT distributions were bimodal in all tasks, with the two strategies differing in speed and sometimes accuracy too. The fast strategy, which was rare or absent in 8- to 9-year-olds, steadily increased through childhood. Its frequency in adolescence remained, however, lower than in adulthood. A mixture model confirmed this developmental evolution, while a diffusion model corroborated the idea that the difference between the two strategies concerns anticipatory processes preceding decision processes. To test the fourth prediction, we conducted an online experiment where 236 participants made numerosity comparisons before and after an instruction favoring either reactive or anticipatory responses. The results provide out-of-the-lab evidence of the bimodal RT distribution associated with sequential comparisons and demonstrated that the proportions of fast vs. slow responders can be modulated simply by asking subjects to anticipate or not the future result of the comparison. Although anticipation of the future is as important for cognition as memory of the past, its evolution after the first year of life is much more poorly known. The present study is a step toward meeting this challenge. It also illustrates how analyzing individual RT distributions in addition to group RT distributions and using computational models can improve the assessment of decision making cognitive processes.