Many decisions are made under the advice of another person. We investigated the environmental circumstances under which two prominent strategies—averaging and choosing—are effective and adaptive and explored how people employ them. We report two experiments, in which participants (N = 111 and N = 90, respectively) provided initial estimates for general knowledge questions that varied in perceived difficulty. In Experiment 2, they additionally received advice in the form of an estimate and confidence rating of another person before providing a revised estimate. We found that items of different perceived levels of difficulty exhibited distinctive statistical properties, thus constituting different social environments. Environmental structure affected the theoretical performance of strategies (such as averaging and choosing), and the ways, in which people integrate advice. We embed our analyses in the frameworks of ecological rationality and the probability, accuracy, redundancy (PAR) model of advice taking (Soll & Larrick’s, 2009; JEP:LMC, 35).