The purpose of this qualitative, multi-case study is to identify the traits three middle school classroom teachers share, which seemingly enable them to successfully engage their students in performance-based activities and assessments. This study investigates the research behind the use of performance tasks, authentic learning and assessment and connects the data gleaned from observations and interviews with participants and administrators to the literature review. Data analysis and summations connect performance tasks to authentic learning but also identify more subjective traits such as relationship building, riskiness in instructional methodology, and the innate skills of a teacher, which appear to enhance students’ learning experiences. Students observed in the classrooms are asked not only to know content and cultivate an appropriate skill base, but also asked to use that knowledge and those skills to solve real-world problems. Data from the three participants not only illustrates the findings of other relevant research, but characterizes the types of teachers who inspire students to perform on a more complex level in order to solve complex problems.