No graduate program can adequately prepare a novice superintendent for the myriad situations she or he likely will face during the first few years. In addition to learning the job, today's superintendent faces challenges unlike those of prior generations. Perhaps the most difficult one is gaining an understanding of how to work effectively with the board of education. To survive the first contract, the 21st century superintendent must satisfy a new breed of board member, one influenced by the Vietnam War and Watergate. This new board member respects results rather than positions of authority and demands proof rather than expert advice. This article provides tips, that hopefully will help with board relations so that the novice superintendent survives beyond the duration of the first contract.