Why should we NOT hire you is one of the oldest, most basic and most passive aggressive questions in interviewing. It's an old school, go-to question to uncover a candidate's weaknesses in the laziest way possible. Instead of asking probing questions and analyzing their answers to determine a candidate's strengths and weaknesses, the lazy thing to do is just ask them - why shouldn't I hire you . There is zero thought put into this question and it gives the candidate zero opportunities to showcase their skills and experience related to the role. Instead of putting the candidate into a negative scenario, how about you ask thought provoking questions that get to what they CAN do for your company? You might get more out of asking what they would like to accomplish if they DID get the job than presenting a scenario where they don't get the job - before they're even done interviewing. Questions like this speak to how Stitch Fix views their candidates and employees. If you tried getting to know the candidate and their skills in a genuine way, you'd have employees on your interview panel that were genuinely happy to work for Stitch Fix - and it would show.