This exploratory study used structured tasks as direct measures of approaches to learning to examine a potentially important domain of school readiness that is comprised of the multiple ways children engage in learning situations. A structured task designed to measure problem-solving flexibility was found to relate to a subset of a teacher rating system that included several aspects of approaches to learning; it predicted achievement both concurrently and 1 year later in a sample of 158 kindergarteners. The direct measure significantly added to the prediction of future achievement even after controlling for prior achievement, receptive vocabulary, and the more global teacher ratings. This study highlights the importance of approaches to learning and offers evidence for the potential of structured tasks to be developed to allow a multidimensional approach to the assessment of this important school readiness domain. Future efforts to guide and enhance children's successful transition into school are also discussed.