Based on extensive research that views leadership as a multi-faceted phenomenon we examined how the relationships between task-oriented and relationship-oriented leader behaviors and career derailment potential vary by observer perspective. We present findings using three different analytical techniques: random coefficient modeling (RCM) relative weight analysis (RWA) and polynomial regression (PR). RCM findings suggest that self- direct report peer and supervisor ratings of leader behaviors differ and are associated with career derailment potential. RWA results indicate that self-ratings matter the least whereas peer ratings of leader behaviors typically matter the most in predicting career derailment potential. PR analyses indicate that career derailment potential is lowest when self-ratings are lower than other ratings of leader behaviors and/or when self–other ratings converge on higher rather than lower ratings of leader behaviors. Implications for leadership and self–other agreement research and professional practice are discussed.