Teaching is complex; teachers and school leaders crave more meaningful collaborative experiences to make sense of that complexity. However, the structural, cultural, and historical factors involved with schooling impede the extent to which teachers can collaborate. Teachers spend five to six periods of the day teaching classes, largely working in isolation from each other; their remaining time is spent tending to administrative tasks, answering emails, or grading. For schools to work around the persistent structural constraints to establish a sincere and thoughtful collaborative culture they must approach collaboration differently. Collaborative cultures emerge from authentic and relevant problem solving. Teachers will see collaboration as an integral feature of their work when the problems they are asked to solve are specific to their practice, are common to a majority of teachers in a particular school, and when solving the problem demands they collaborate with colleagues.