When it comes to interviewing or interrogating someone, it's often necessary to ask pointed questions. However, using the same phrase repeatedly can get monotonous. Here are some synonyms for "asks pointed questions" that you can use to mix things up: queries pointedly, probes incisively, inquires acutely, interrogates intently, examines intensely, challenges directly, quizzes intensely, presses insistently, grills relentlessly, and cross-examines thoroughly. These synonyms convey an assertive yet tactful approach to discovering information and can help you avoid sounding repetitive in your questioning. By using these synonyms, you can engage in effective communication without losing the interest of the person you're questioning.