What factors affect whether learners adopt a new problem- solving strategy? Potential factors include learners’ evaluations of alternative strategies and the degree of similarity between their existing strategy and the alternatives. A first step in answering this question is investigating how people evaluate strategies. This exploratory study investigated how people evaluate strategies for solving algebraic word problems, and how these evaluations vary as function of individual differences. Undergraduates rated three strategies on six dimensions and judged each pair of strategies for similarity. Factor analysis showed that evaluations could be reduced to two constructs: efficiency and intuitiveness. We calculated factor scores for each participant for each strategy. Efficiency did not predict similarity ratings on its own, but it did interact with Need for Cognition. These results suggest stable learner characteristics and moment-to-moment evaluations of strategies influence judgments about strategy similarity.