When the dark side of leadership emerges, organizational catastrophe is just a step away. Financial news proves this year after year. For instance, former CEO Adam Neumann contributed to devaluing the commercial real estate company WeWork by approximately $37 billion in mere months.1 Now, we all know that the dark side of personality can derail everyone’s behavior from time to time. But leadership derailment is a higher-order problem. As in the case of WeWork, the dark side of leadership can result in bankruptcy and ruin.