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The worst one I had was a panel interview (6 people) where one person asked me if while working at my retail store if I ever tried on the clothes and walked out with them on (I'm black).... the interview ended shortly after that question. This was right before covid hit.
The guy said, "You're a young one, aren't you". I was 38 at the time and he was trying to get around the illegal question of age.
More surprising than awkward:
As a young marketer I was trying to break into strategic planning at a big agency. After a range of technical questions, my interviewer (who later became my manager) stunned me with this question.
"Tell me about your best friend. What makes you best friends?"
It seemed wildly random in the moment. But now I see it was a shortcut to test my human insight and ability to make sense of something I likely hadn't thought deeply about, on the fly.
He's retired now, and I'm sure HR would never approve of his question now. But it has always stuck with me as a brilliant move to gauge someone's ability to find and articulate meaning on the fly.
They generally discourage questions about a candidate's personal life that don't directly relate to the responsibilities of the role. Things like "what do you do for fun?" "where did you grow up?" and yes, "who's your best friend?"
As an intern I got asked: Why should I hire you when I have candidates from *nearby top-tier* universities when you went to *average college*
I hope you walked out.
“If the client came to you with an unsolvable problem, how would you solve it?”
I might ask about the problem. Like, is the unsolvable problem the real problem? Or is it just what the client thinks is the problem. Hopefully we could chat about that and then just move on 😂
Rising Star
"Did anyone tell you this is not a paid position?"
I spoke with an interviewer about all the times we got arrested. I got the job
If you were an animal what would you be and why. Seeing as I was interviewing for an AS role, not a camp counselor, I was NOT expecting this question. Can't even remember what I said but I didn't get a second interview so they obviously did not like the animal I chose.
"What do you do better than your current boss?"
Pissed me off so much. My boss at the time was great, so it was a needlessly contentious way to phrase it. It may seem okay at face value, but the dude's entire demeanor was stand-offish and antagonistic. Hard pass.
I had an interviewer ask my age flat out.
Back in 2004, I was asked, "What's your value prop?" I was interviewing for HR, I had no idea what that meant. I got the offer but turned it down because, well, value prop.
Not most awkward question per se. But I was asked a question about how I incorporated new technologies into my worl and I started raving about the creativr technologist at the shop I was and how we worked well together and the interviewed said "yeah I know her, it's my ex wife"
Overheard:
CD: Where are you from?
Interviewee: Iran
CD: Why are you white?