Asking thought-provoking questions is one of the most important, enjoyable, and satisfying aspects of my job as CEO. At the heart of critical thinking is the ability to formulate deep, unusual, and effective questions. As this article advocates, first formulate and then loosely hold onto a hypothesis, but also be willing to fundamentally reconsider your initial conclusions without being defensive. Second, listen more than you talk through active listening. Third, leave your queries open-ended, by avoiding yes-or-no questions. Fourth, consider the counterintuitive to avoid falling into groupthink. Fifth, take the time to sleep on it, rather than rush to a conclusion too quickly. Lastly, do not hesitate to ask difficult follow-ups. This process can and will up your communications game and bring more insight and game-changing conclusions to your critical thinking. Please reach out to me to discuss your success with this approach.