Modeling, which enhances skill acquisition, is an often-used means of conveying information to learners. While models typically provide a demonstration of correct movements or successful performance, skill acquisition is also enhanced by observing a “learning model,” who practices, receives feedback, and improves. The effect is proposed to be due to the observer engaging in problem-solving, error detection, and strategy evaluation. The purpose of this experiment was to examine the effects of observing one or two learning models in combination with physical practice, and the temporal placement of model observation during physical practice, on the acquisition and retention of a motor skill. College students practiced a 3 × 6 × 3 cup stacking task in groups of three, and had opportunities to observe their peers’ physical practice. Treatment groups differed in the order of observation and physical practice; some participants engaged in physical practice prior to observation, while others observed one or two learning models before practice. Data indicated observation prior to engaging in physical practice enhanced learning. In addition, participants were able to identify strategies they observed that enhanced skill performance. These results support and add to existing research on modeling, and provide insight into the types of cognition that occur during observational learning.