The phrase "asked pointed questions" can be replaced with a variety of synonyms depending on the context and tone of the conversation. Some alternatives include "interrogated," "grilled," "pressed for answers," "probed," "queried," "cross-examined," and "challenged." These synonyms all convey a sense of intensity and scrutiny, suggesting that the questions being asked are not simply casual inquiries, but are designed to elicit specific information or reveal the true motives of the person being questioned. Choosing the right synonym can help to add depth and nuance to your writing, and can help to convey the precise tone and intention of the conversation.