High-quality training environments are essential for athletic peak performance. However, recent research highlighted that athletes’ personality characteristics could undermine effective training. The current set of studies aimed to examine whether specific transformational leadership characteristics displayed by the coach would moderate the potential negative impacts of 2 personality traits (i.e., extraversion and neuroticism) on training behaviors. In Study 1, 99 university athletes completed questionnaires assessing personality, transformational leadership, and training behaviors. In Study 2, 84 high-level athletes completed the same personality and transformational leadership questionnaires, but the head coaches assessed their training behaviors. Both studies showed that coaches’ high performance expectations moderated the extraversion–distractibility relationship. Furthermore, both studies demonstrated that the relationship between neuroticism and coping with adversity was moderated by coaches’ inspirational motivation. The findings indicate that extraversion and neuroticism can negatively relate to training behaviors, but such effects can be moderated by certain transformational leadership behaviors.