The document discusses four reasons why leadership training often fails in organizations: 1) Overlooking individual context and assuming a one-size-fits-all approach, 2) Not addressing behavioral change at an individual level, 3) Lacking commitment to change from employees, 4) Failing to properly measure results and track improvements over time. It emphasizes the importance of customizing leadership development to each individual employee and assessing skills development rather than just satisfaction to ensure training success and return on investment.