Background/Context: A growing literature describes multiple benefits of social perspective taking--many of which are particularly important for schools. Despite these potential benefits for administrators, counselors, teachers, and students, little is known about social perspective taking as a process. Purpose/Research Question: If educational researchers are ultimately to design interventions to help improve the perspective-taking capacities of those in schools, they need to fully understand the underlying process. Particularly important is the need to understand: What initially motivates individuals to take the perspective of others? Participants: To investigate this question, a sample of 18 adults from an array of different professions (who were nominated as adept perspective takers) and 13 high school students (who were nominated as struggling with social perspective taking) participated in the study. Research Design: Participants completed a survey, a performance task, and in-depth interviews as part of this mixed-method exploratory study. The interviews served as the primary source of data and were coded for evidence of what triggered (or inhibited) participants' motivation to engage in the social perspective-taking process. Findings: The interview data established the existence of 13 specific factors that impacted participants' motivation to engage in social perspective taking across a wide array of contexts. Seven factors generally enhanced individuals' motivation to engage in social perspective taking; three factors were mixed; and three factors inhibited their motivation. Conclusions/Recommendations: This research indicates that not only might individuals be motivated to engage in social perspective taking through multiple pathways, but these pathways might be combined and/or interact with one another. These motivating factors raise important issues for further research. In addition, at a practical level, they provide a foundation for developing structures to motivate individuals in schools to engage in perspective taking more often.