Boards believe equity alignment secures commitment. In reality, poorly designed compensation often creates a countdown timer to CEO risk aversion and exit. In this episode of The Boardroom Daily Brief, Ash Wendt breaks down the compensation cliff, the moment when vesting schedules quietly reshape decision making, stall transformation, and push strong leaders toward safety. This is a deep dive into how incentive design, not character, causes strategic hesitation, talent loss, and underwhelming outcomes, and what boards must change to stop programming the very behaviors they claim to want to avoid.