Teacher mentoring programs are commonly used for entry year teachers to provide support and encouragement. These programs are often not successful without quality mentors. This qualitative case study seeks to explore the motivational factors inherent in the Learning Matters mentoring programs at two selected middle schools to determine the impact motivational factors have on the mentors participating in the program using the lens of Self-Determination Theory. The study participants were the building principals and three veteran mentor teachers at each site. Data were collected through interviews of the administrators and mentor teachers, observations of the Learning Matters meetings, and documents.