Leaders complain that people agree with them too much and do not assert their true opinions and ideas. But then when they do so, leaders get upset and view their subordinates' assertive behavior as disrespectful. Many leaders, unfortunately, desire courage but reinforce subservience. A superintendent's most important job is to inspire courageous behavior among those he/she leads or influences. The author argues that superintendents need to be courage builders. Being a courage builder means influencing people to move outside of their comfort zones. Moving staff out of their comfort zones is the opening step for promoting personal growth and organizational development. The author believes the entire organization wins when everyone shows up to the office each day with more courage, enabling them to take on harder tasks, deal better with change, and speak up more willingly about important issues.