Based upon multi-source data collected in a longitudinal research design and analyzed via correlation, regression, and structural modeling, we found that an organizational culture that involves working constructively with errors and mistakes was associated with higher motivation to be a leader and with higher motivation to develop leadership capability among individual employees from across diverse occupations and organizations. Error management culture further had indirect effects on key individual outcomes such as leadership behavior/performance as well as indices of ascendancy and career success (i.e. increased leadership responsibility and promotions). We also found that motivation to develop leadership capability was a better predictor of leadership behavior and other success outcomes than motivation to lead. These are novel and valuable contributions to the literature at a time when organizations are struggling to better understand challenges such as managing leadership development behavior and creating cultures that support innovation and growth among employees.