Paid time off (e.g., sick, vacation, personal time) is an important element of a school’s overall compensation and benefits program.1 As a robust employee benefits and compensation program is one of ISM’s Stability Markers®, ISM encourages schools to be as generous in this area as financially possible. However, some schools extend this generosity in the form of paid leave “banks” in a way that creates risk for the school. This article examines those risks and proposes alternate paths to reach the same desired end—that is, attending to employee needs in a way that is compassionate but also significantly less risky.