Why do people shift their strategies for solving problems? Past work has focused on the roles of contextual and individual factors in explaining whether people adopt new strategies when they are exposed to them. In this study, we examined a factor not considered in prior work: people’s evaluations of the strategies themselves. We presented undergraduate participants from a moderately selective university (N = 252; 64.8% women, 65.6% White, 67.6% who had taken calculus) with two strategies for solving algebraic word problems and asked them to rate these strategies and their own strategy on a variety of dimensions. Participants’ ratings loaded onto two factors, which we label quality and difficulty. Participants’ initial evaluations of the quality of the strategies were associated with whether they used the strategies at posttest, and this effect held even when controlling for individual and contextual factors. However, people’s evaluations of the difficulty of the strategies were not consistently associated with their later adoption of those strategies. We also examined individual and contextual predictors of strategy ratings and strategy adoption. Participants’ need for cognition and their spatial visualization ability were associated with their strategy evaluations, and the framing of the story problems was associated with their strategy adoption. The findings highlight that strategy adoption depends on multiple interacting factors, and that to understand strategy change, it is critical to examine how people evaluate strategies.