Many effective psychological interventions change maladaptive interpretations of oneself or of one’s context by offering more adaptive narratives, which are associated with desirable responses and outcomes. Psychologically wise interventions from the social-psychological tradition have used this approach to great effect in improving important outcomes across a variety of life domains—including, but not limited to, academic performance, physical and mental health, relationships, organizational culture, and civic behavior. Although these psychologically wise interventions target people’s narratives, they do not focus on teaching effective strategies for pursuing valued goals—let alone a sustained mental habit of considering strategies that can make goal pursuit generally more effective. How might we better support and maintain adaptive narratives that psychologically wise interventions offer, especially in goal-directed, effective, and generalizable ways? I propose a complementary approach: guiding people to ask and answer strategic questions. These are questions that can elicit strategy generation, access, and use. As I explain, asking and answering strategic questions can elicit adaptive appraisals and responses to adversity. Importantly, people can learn an orientation toward self-prompting strategic questions. Understanding and intervening on strategic questioning and answering offers new frontiers for research and practice.