When I was 12 or 13, I was obsessed with reading the real-life embarrassing stories in Seventeen magazine. I used to post up in the library and read every back issues’ stories. They were incredibly cringe and gave me an incredibly strong but irrational fear of getting my period in public while wearing white jeans (iykyk….) but these tales were so compelling because they happened to real people (allegedly!).
Random side note: these are still being collected from the teens of today, if you want to relive the second-hand mortification. Still convinced they’re sponsored by Big Tampon but whatever.
This love of other people’s, uh, testimony has also continued into my not-so-secret love of reading Reddit’s “Am I the Asshole? (AITA)” where both clinically insane and relatively normal people let randos judge their worst behavior and life experiences. I LOVE the cringe. Feast your eyes on such gems as “AITA for giving my mom and stepsister the benefit of the doubt that they did not know it was rude to wear white to a wedding?”, “AITA for booking my toddler a first class seat?”, and of course, the tragically now-removed classic, “AITA for making our guests participate in our puppet themed wedding?”
Spoiler alert: the more insane the title, the less likely they are to be assholes. The true assholes have titles that seem sane.
BUT I DIGRESS.
Why am I talking about real life cringe?
I’m kicking off a fun series of asking friends, former colleagues, internet strangers, and anyone who will speak to me, to tell us their worst stories about bosses, managers, and leaders. The juicy details will be coming.
OBVIOUSLY we’re not trying to get sued so going to keep it nice and anonymous.
Going to kick it off with some fresh, light anecdotes to whet your appetites.
Enjoy.
From a teacher
“[A former principal] sent a resignation email after it was discovered he was embezzling money and having an affair with our assistant principal. He absconded to Mexico.” The email incudes the line “Be Blade, not a Vamp. The price of not being a Vampire killer is not just that [Redacted School] will fail. You also may lose yourself in the process.”
From a recruiting consultant
“In agency, we had a member of our company’s senior leadership team who collected all the junior staff into a meeting to get our feedback on how the experience of junior staff could be improved. Morale was low. They clearly did not want to get actual feedback and grew visibly frustrated as the meeting went on and people spoke up respectfully and made suggestions.
Finally I asked a pretty innocuous question and the leader threw their pen directly at me from across the board room table. It was silent for a few minutes and then they wrapped up the meeting. I couldn’t believe it happened until some of the other staff came up to me later to commiserate. There was no follow-up or consequences and I left the firm soon after”.
From a former chief of staff
“I had a very senior boss with whom I frequently had to travel, mostly commercial. Because his airline status meant flights wouldn’t depart without him, he delayed countless planes sitting in the lounge making and taking calls, dismissing the polite but increasingly harried pleas of airline staff.
He would throw a temper tantrum if he didn’t get seat 1A, complaining that it was my fault the airline had so badly misjudged the relative importance of its first class passengers.
If he didn’t want to work during the flight, he would demand that I sit back in economy so I couldn’t disturb him. On more than one occasion, he made this decision only as we were boarding, leaving me to negotiate with flight attendants the worst upgrade of some unsuspecting passenger’s life”.
From financial services
“My firm had a client appreciation holiday party one year that got a little messy. The clients, mostly young (male) bankers, all got blackout drunk and weird with all our female staff. One of my own junior clients harassed me, and groped me and my senior colleague before one of our male colleagues kicked him out gracefully.
When we told our boss the next day about the client’s behavior, she removed us from the client account and did not do anything else about it, except to lecture us on appropriate workplace behavior. A man took over that account.”
Another financial services, this one extra insane
“This happened a long time ago (the 90s) but my former manager grabbed my boobs on the trading floor in the middle of the day surrounded by colleagues. I slapped him in the face, he said nothing, and after that we worked really well together”.
From a lawyer
“A former boss filed a fraudulent bankruptcy…or something along those lines, and we only found out when he mysteriously told us he owed us retirement matching funds three years later… because the court ordered him to pay it out. A lawyer friend later saw some of the filings and told us the tea”.