Why do hiring managers ask tricky job interview questions? They ask because for them, hiring you is a risk. They try to minimize the risk by asking questions designed to uncover problems with you or your qualifications. Answer them well, and they will feel comfortable offering you the job. Here are five tricky job interview questions you should be ready to answer. Tricky Question #1 – Tell Me About Yourself: This is commonly asked in social settings, so many people respond with a social answer—this is a big mistake. Read more.