I had an interview with a CTO back like 2 years ago, I already passed the 3-4 interviews 2 of which were technical and I am on this cultural fit interview with the CTO. The guy enters the call everything seems normal and he begins with his questions which were absolutely insane. First he asked me how did I improve in my work, since I work in cyber I explained to him that I am following latest trends, and getting security certificates like OffSec and other hands on stuff, even CTFs. He is not satisfied he asked me about specifics and to dive deep, okay.. I've explained to him how OSCP, OSWE and OSEP worked and possibly even shared some of the exam ranges scenarios, again he wasn't satisfied and asked for specifics I am already baffled and I was thinking "Does he want me to share the CTF flags or what". Anyway after back and forth with me saying that I don't understand what he wants me to say, he moves forward with "Now what about outside working hours". I sighed and explained that this is taking at least 90% of my free time as well, but he kept asking that he does not care about work and wants to know what I do outside work. Okay I play table tennis quite often and I train it, HE IS NOT SATISFIED (mind you he asked for specifics as well) and in the end he sighed and just said "so you are not improving outside work". I am on the verge of clicking the end meeting button but I kept going. Next question was, have I done any proactive work during work hours, I explained what I did, what tools I've written for the developers and he again asked for SPECIFICS, I said that at this point I am starting to worry about my NDA, and explained that I won't be sharing what I did specifically. He was frustrated and started explaining me that he does not know my clients or whatever or anything about me so it won't matter, which is absolutely laughable but I refused to share anything. Next thing he said is that I am bombing the interview and he has 0 value from this conversation, and I was like okay sure I didn't know that I should bring value into your company/you without even starting. He was now really frustrated started to use words like "fucking" and so on, explained to me how the interns in the company were having a better answers and how his mom would do a better job at this. I was like "???? lmao". Now telling you this I am not sure why I did not quit the meeting but here we go the next question, which I do not remember exactly but I distinctly remember that he said "that's a perfect answer". And since this is becoming long enough I would spare the rest of questions which were absurd once again. Needless to say that I wasn't chosen nor I would have chose them even if this was somehow a pass.

Man, I would never want to be in your shoes that day. What a pain.