Short-sighted decisions can have devastating consequences, and teaching people to make their decisions in a more far-sighted way is challenging. Previous research found that reflecting on one’s behavior can boost learning from success and failure. Here, we explore the potential benefits of guiding people to reflect on whether and how they thought about what to do (i.e., systematic metacognitive reflection). We devised a series of Socratic questions that prompt people to reflect on their decision-making and tested their effectiveness in a process-tracing experiment with a 5-step planning task ( $N=265$ ). Each participant went through several cycles of making a series of decisions and then either reflecting on how they made those decisions, answering unrelated questions, or moving on to the next decision right away. We found that systematic metacognitive reflection helps people discover adaptive, far-sighted decision strategies faster. Our results suggest that systematic metacognitive reflection is a promising approach to boosting people’s decision-making competence.