Today, more than ever, teachers must work effectively and efficiently to meet seemingly contradictory demands placed on them by society. On the one hand, school personnel are tasked with attaining and publicly reporting high levels of student achievement in response to No Child Left Behind. On the other, school personnel must ensure that students learn 21st century skills such as critical thinking and problem solving, collaboration, adaptability, entrepreneurialism, effective oral and written communication, and accessing and analyzing information. This dichotomy challenges educators to prepare students to select the right answers on standardized tests and, at the same time, to critically analyze the myriad possible solutions that may be appropriate for addressing problems in daily life. Teachers must prepare students to think both inside and outside the box. This article presents a brief overview of distributed leadership and gives insights gained from creating and leading a distributed leadership team for three years at a high school. Working with a team offers benefits; yet, to ensure smooth operation, certain factors must be taken into consideration. The author offers suggestions for both principals and teachers who are becoming more involved in distributed leadership. Ultimately, the goal for teacher-leaders is to enjoy and benefit from the experience as well as to make worthwhile contributions where it counts--in the teaching-learning arena.