I was in the final stage for a YC company and met the CEO at the final interview. I had already kind of messed up the technical interview so I wasn’t feeling too great about talking to him to begin with. He opened with an introduction of himself and told me the history of the company which was fine, and asked if I had any questions. I asked him what were some challenges that he faced during the growth of the company. his answer was that “people challenges” were among the hardest of problems that he had. Fair enough, but he gave only one example: having to let go of an engineer that was underperforming.
I didn’t get the offer, but I didn’t want to work for somebody who would say that to an engineer applying for a job. (plus they had the weirdest stack i’ve ever seen)