As resources shrink, the need to do more with less becomes critical. As a business CEO turned superintendent, the author has seen firsthand that many options exist, but none are fun, easy, or politically rewarding. In 2005, he launched a 50-person listening tour with school committee members, central-office staff, curriculum leaders, and principals. They found out that the school faced a structural deficit each year. Budget cuts were a given. With this backdrop, he sets out to do more with less. It turned out they had enough money; they just spent it on the wrong things. With the new strategy in hand, they now knew what was needed: more reading teachers, paid mentors, elementary math coaches, a better student information system, a data analyst, and stipends for teachers to develop the common curriculum and district-wide formative assessments.