Four studies explored whether perspective-taking and empathy would be differentially effective in mixed-motive competitions depending on whether the critical skills for success were more cognitively or emotionally based. Study 1 demonstrated that individual differences in perspective-taking, but not empathy, predicted increased distributive and integrative performance in a multiple-round war game that required a clear understanding of an opponent’s strategic intentions. Conversely, both measures and manipulations of empathy proved more advantageous than perspective-taking in a relationship-based coalition game that required identifying the strength of interpersonal connections (Studies 2-3). Study 4 established a key process: perspective-takers were more accurate in cognitive understanding of others, whereas empathy produced stronger accuracy in emotional understanding. Perspective-taking and empathy were each useful but in different types of competitive, mixed-motive situations—their success depended on the task–competency match. These results demonstrate when to use your head versus your heart to achieve the best outcomes for oneself.