Meeting the increased demand for rheumatology care in the future will require changing the way rheumatology is taught. Enhancing rheumatology education may encourage more trainees to pursue rheumatology careers and improve knowledge about musculoskeletal conditions for primary care providers. However, the inherent uncertainty that surrounds the etiology, diagnosis, and treatment of many rheumatic diseases presents a unique challenge to rheumatology education and demands a distinct approach. By mastering the art of questioning, faculty can improve a learner's ability to understand and remember the material, apply knowledge in new settings, overcome cognitive biases, support an environment of inquiry, and develop metacognition, even under uncertainty. Trainees should also learn the craft of asking questions as a method of studying, a practice that stimulates curiosity, and a tool that will help them become life-long, self-directed learners. In this guide, we present the evidence behind the power of questions, provide a model for the best use of questions in various teaching venues, and recommend specific techniques for effective questioning. This article is protected by copyright. All rights reserved.