Derailment is spoken of when leaders, who have been successful for a long time, stagnate in their rise and/or completely deviate from their career path (e.g., are dismissed). Although a large part of the leaders experience derailment over their (professional) lifespan and this is very stressful for the leaders themselves and associated with high costs for the companies, this topic is widely tabooed and suppressed. This chapter aims to show ways to recognize the seemingly sudden derailment of leaders early on, to react adequately in situations of failure, and to find a productive way to deal with failure.