This chapter describes how to approach, create, select, and evaluate the assessment items or methods frequently used in clinical education. In classroom settings, instructors are commonly asked to write multiple-choice test questions, but without question-writing training, the result is often poorly written, flawed questions that test fact memorization and recognition rather than the application of knowledge. In clinical settings, instructors must give feedback and make curricular progress decisions based on observation and objective skills testing. Complex skills like clinical reasoning as demonstrated in patient notes can be difficult to grade fairly and consistently, especially when multiple instructors are doing the evaluation and providing the feedback. The varied assessments in the clinical setting can be difficult to bring together to determine if a learner is sufficiently competent to progress in the curriculum. Thoughtful approaches to evaluating and compiling learners’ experiences and work products in complicated and unpredictable patient care settings demand explicit expectations and as much objective measurement as possible. This chapter presents an overview of assessment methods that encourage student learning. It also urges a comprehensive approach to implementing assessment, setting standards, and using assessment results to inform learners and the curriculum.