Driver training has the potential to keep older adults safe behind-the-wheel for longer, yet there is limited evidence describing factors that influence their willingness to participate in training. Focus groups with community-dwelling older drivers ( n = 23; 70–90 years) and semi-structured interviews with driving instructors ( n = 6) and occupational therapists ( n = 5) were conducted to identify these factors. Qualitative descriptive analyses highlighted how self-awareness of behind-the-wheel abilities in later life can influence an older adult’s motivation to participate in driver training, as well as their willingness to discuss their behaviors. Collision-involvement and near-misses prompted participants to reflect on their driving abilities and their openness to feedback. Participants’ preferences for learning contexts that use a strengths-based approach and validate the driving experience of older drivers, while providing feedback on behind-the-wheel performance, were raised. Older driver training initiatives that consider the needs of the aging population in their design can promote road safety and community mobility.