With organizations of all sorts facing increased urgency and unpredictability, being able to ask smart questions has become key. But unlike lawyers, doctors, and psychologists, business professionals are not formally trained on what kinds of questions to ask when approaching a problem. They must learn as they go. In their research and consulting, the authors have seen that certain kinds of questions have gained resonance across the business world. In a three-year project they asked executives to brainstorm about the decisions they’ve faced and the kinds of inquiry they’ve pursued. In this article they share what they’ve learned and offer a practical framework for the five types of questions to ask during strategic decision-making: investigative, speculative, productive, interpretive, and subjective. By attending to each, leaders and teams can become more likely to cover all the areas that need to be explored, and they’ll surface information and options they might otherwise have missed.