Think Your Job Is Bad? 3 Strange Workplace Horror Stories

Think your job is bad?

3 Strange workplace horror stories

With Administrative Professionals Day this Wednesday, assistants across the country will receive cards recognizing their often-thankless work. But given the expectations of today’s demanding executives, some support staff deserve way more than a drugstore gift.

Here, three New York worker bees — who prefer not to use their last names for professional reasons — share battle tales of the tasks that were definitely not in their job descriptions.

The funeral fill-in

Suzanne had been working for a Long Island nonprofit CEO for five years when, in 2013, he approached her with a task even he knew was unorthodox.“He sat me down right after his brother passed away,” recalls Suzanne. “And he said, ‘I have a somewhat strange request. Everyone is expecting me to make a speech at the funeral, and I am drawing a blank. Can you write something?’”

Suzanne found the request bizarre — she’d never met her boss’ brother and knew nothing about their relationship. Still, she reluctantly agreed to compose a speech based on information she found about the sibling online.

“I put together what I thought was a draft, thinking that [my boss] would make appropriate changes,” she says. “Then, at the funeral, I was very surprised to hear him read literally word-for-word, verbatim, what I had written — nothing added, nothing crossed off.

“My boss and I never spoke of it.”

The cash and carry

As an executive assistant to two hotshot investment bankers, Allison was used to tackling one “ridiculous” personal errand after another. But nothing could have prepared her for the day, in 2003, when one of her bosses asked her to accompany him to a Midtown bank — then nonchalantly showed her a withdrawal slip for $35,000.“He told me nothing about what we were doing,” says Allison, then 24.

At the bank, the duo were whisked into a private room, where her boss explained the cash was for a pair of diamond earrings for his soon-to-be wife. Allison’s task? To transport the cash to the Diamond District — to purchase the bling tax-free.

“The bank asked if I wanted an armored car to take me, but my boss said, ‘No, she’ll be fine,’ ” she recalls.

“It felt like I was doing a drug deal,” adds Allison. “It was my entire yearly salary in a paper bag!”

Allison finally arrived at the Diamond District, handed off the moolah and received a small box in exchange. She hurried to deliver it to her boss, who offered only a simple “Thanks.”

“He was totally blasé,” says Allison, “like he’d just given me $20 to get him a roast-beef sandwich.”

The T.M.I. test

When Renee took a job supporting a Midtown p.r. exec in 2006, she thought she’d learn a lot about the industry — not check off her boss’ personal to-do list.“She used to have me pretend to be her pretty often,” says Renee, now 32. “I would have to call up her real estate management company about not getting ‘my’ lease renewal in on time.”

But one day, her boss’ impersonation requests turned “creepy.”

“She said, ‘I think I have a urinary-tract infection. I need you to call my gynecologist, say you’re me and complain of really bad symptoms so I can get an appointment right away.’”

Renee was still so new to the corporate world, she didn’t think to push back.

“I called up the doctor, played up the symptoms really descriptively and acted really scared,” she says.

She says her boss appreciated that she’d nabbed a plum appointment — though Renee’s parents couldn’t believe how their daughter spent her work day.


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