The Teaching Internship is a credit-bearing program composed of undergraduate near peer instructors (teaching interns, or TIs) that offers supplemental assistance for students in the General Chemistry courses. With fellow undergraduates serving as a role model and student–faculty liaison, the benefits of near peer instruction have been well-documented. Because TIs develop a dual role of student and instructor over time, they afford a unique opportunity to explore the middle area of the expert/novice spectrum. Identifying the most influential components of the TI role may allow practitioners to implement these components in other ways for different groups of students. The present work provides a description of the TI model and uses a mixed-methods approach to analyze how the peer leadership role impacted the TIs’ attitudes about learning chemistry. Quantitative results show that TIs do hold predominantly expert-like learning attitudes compared to the General Chemistry population from which they are selected; however, evidence of novice thinking is still observed in some areas. This survey data was then used to inform a qualitative approach. Further analysis indicated that TIs’ responses on survey items were context-dependent, and that peer leadership experiences were associated with expert learning attitudes and appear to be influential in the development of these attitudes. These findings suggest that these factors should be taken into account when drawing general conclusions from survey results.