The development of executive function (EF) has garnered attention in recent years because of its association with many positive outcomes. Although evidence suggests these skills can be trained, little research has focused on the processes that promote strong EF skills in high-risk children. Study 1 sought to investigate spontaneous self-regulatory strategies in 138 4- to 7-year-old homeless children during an EF task and to understand the relation between verbal and physical strategies, performance on EF tasks, and school outcomes. As hypothesized, results indicated that physical strategy use was significantly related to general EF, and that EF mediated the relation between physical strategy use and academic achievement and peer competence at school. Study 2 sought to investigate whether similar strategies can be trained and are related to performance on a delay task. 106 4- to 7- year-old homeless children were randomly assigned to training and control groups, and performance on two delay tasks was examined. As expected, children in the training group displayed significantly more strategies on the training task than did children in the control group and that these strategies were significantly related to task performance. However, there were no overall group differences in performance. Exploratory analyses revealed some evidence for a significant relation between training and performance only for older children. Additionally, results demonstrated some transfer of trained strategies to a generalization task, although these were not related to performance. Overall, evidence indicates some potential benefit of training children to use strategies during delay tasks, with implications for interventions aimed at promoting EF development and long-term school success.