The development of radically creative ideas entails greater risk and uncertainty because it makes existing knowledge in the organization obsolete. Yet we have known little about how the organizational context affects employees’ ability to feel secure and capable of taking risk, changing their radical creativity. This study explored an expectancy mechanism through which organizational error management culture motivates the radical creativity of employees with different motivation orientations by shaping their psychological safety. Through a multilevel moderated mediation analysis based on the data collected in a time-lagged field study, we found that organizational error management culture has a positive effect on employees’ radical creativity via increasing their psychological safety while organizational error aversion culture exerts a negative influence on employees’ radical creativity through decreasing their psychological safety. In addition, we found promotion focus strengthens the positive indirect effect of organizational error management culture and weakens the negative indirect effect of organizational error aversion culture on employee radical creativity. Theoretical contributions to the creativity literature and the error management literature were discussed, followed by practical implications.