Synthesizing the theories of transformational leadership (Bass, 1985; 1997) and self-determination (Deci & Ryan, 1985, 2000), this research investigated the mediating mechanism of the satisfaction of three basic psychological needs affecting the positive relation between managers’ transformational leadership (TFL) and subordinates’ autonomous motivation (AM) at work in two culture-specific samples from China and Canada. Cross-cultural comparisons were conducted to test if individual collectivistic values predicted autonomous motivation and if they positively moderated the relation between TFL and AM. Hypotheses were tested using hierarchical linear modeling (HLM) which allows multi-level investigation in nested data. Two HLM models were analyzed in each sample, in which TFL was treated as an individual level variable (subordinates’ perception) and a group level variable (mean of subordinates’ evaluation). The results supported in both countries the positive relation between TFL and AM. In China, the satisfaction of the need for autonomy (marginally) and relatedness were found to mediate the relation between perceptions of TFL and AM. When testing for direct relations between basic needs satisfaction and AM, positive main effects for autonomy and relatedness need satisfaction were found in China. In Canada, besides the positive main effect of autonomy and competence need satisfaction on AM, relatedness also significantly predicted AM when autonomy was high. In addition, having high collectivistic value was related to higher AM but it did not significantly moderate the positive relation between TFL and AM in the cross-cultural comparison. Implications for management practice and limitations are discussed.