11 Of The Wildest, Most Ridiculous Requests Assistants Have Gotten From Their Bosses


What’s the most ridiculous thing a boss has asked you to do?

For some of us, the answers may be rather tame. Yes, demanding and micromanaging bosses are horrible, but they are an unfortunately common trial many of us endure at some point in our careers. But if you have worked as an assistant of any kind, your stories are likely wilder, weirder and contain deeper personal transgressions.

That’s what Jeremy Burrows found out when he surveyed executive assistants about the most ridiculous thing an executive had asked them to do. As the executive assistant to the CEO of Capacity, author of “The Leader Assistant: Four Pillars of a Confident, Game-Changing Assistant” and host of “The Leader Assistant” podcast, he’s heard of bosses who made their assistant their tailor, their cleaner, their private investigator and their reluctant servant.

“Unfortunately, I’m not surprised, as I’ve heard and experienced situations like these,” Burrows said. “However, these stories should be a firm reminder to assistants everywhere that life is too short to work for toxic and abusive bosses.”

HuffPost asked assistants to answer this question, too. Their responses, along with some from Burrows’ survey, are detailed below.

The Boss Who Needed Help Wiping Porn From His Computer

“‘My wife is coming in later. Can you order some Kate Spade perfume and get all the porn off my computer?’ Shaking my head.” –– Britt Roberts, then an administrative assistant based in Charlottesville, Virginia

The Boss Who Snapped Instead Of Using Words

“She snapped her fingers when she wanted something. Would shout ‘FOOD!’ from her office, meaning ‘Get me lunch.’ I was in the beginning of my admin career. I’ve come so far, and while that was painful, it made me more sympathetic to admins who struggle with tyrants. –– anonymous executive assistant

The Boss Who Wanted Someone Followed To An Appointment

“[The wildest request was being asked to] follow someone to their appointment to see if they were actually going to a job interview. I was genuinely afraid of this man’s temper, so I couldn’t refuse him. Instead, I pretended to follow the person and lied to him — anything to keep him in a halfway decent mood.” –– anonymous executive assistant

The Boss Who Wanted Help Covering Up An Affair

“It’s not unusual to go shopping for anniversary and birthday and Mother’s Day gifts for the wives, but I would have to go do the shopping for his wife, especially around Valentine’s Day, and he would have to do the shopping for his mistress, and then I would have to give the gifts to both of the people.

It was like, ‘OK, well, what am I going to do?’ We’d come back to the office, we’d swap gifts. I’d overnight the gift for the mistress, and then he would take the gift home for the wife.

One time I was just so upset at what he was doing to his wife that I accidentally on purpose bought these ridiculous, over-the-top expensive chocolates that his mistress loved. It was the middle of the summer and they were going down to a Southern state, so I sent them three-day FedEx. I knew they would arrive melted.” –– D.D., an executive assistant

The Boss Who Banned Morning Greetings

“‘Can you not say good morning to me when I arrive at the office? It causes me to lose my focus.’” –– anonymous executive assistant

The Boss Who Asked His Assistant To Dispose Of A Dead Bird

“A bird flew into the grill on my boss’ car while he was driving to work — it didn’t survive — and once he got into the office, he used my ruler to wedge that poor bird out and asked me to get rid of it and handed me my ruler back.” –– anonymous executive assistant

The Boss Who Wanted Help Scheduling Very Personal Appointments

“When I was working as an EA in consulting, I had an executive who was a very busy partner and she was pregnant. She basically tells me, ‘I feel awkward asking you this, but just wondering if you wouldn’t mind scheduling my OBGYN appointments.’ And honestly, not the oddest request I’ve ever gotten. I didn’t think anything of it. I said sure; I’ve got kids myself, I’m not a stranger to OBGYN appointments. I call the office and we are going through the standard intake forms, but some of the questions that the doctor asks are really, really personal.

It took me so off-guard. I honestly lost my train of thought for a second and didn’t know how to respond to it. One of the intake questions was, for example, ‘How frequent is your sex life?’ I was just like, ‘OK, I wouldn’t know that.’ As she got to question number two, which was like ‘Are your periods regular?’ I was just like, ‘Let me jot down the questions.’

It was very awkward because it’s like, ‘OK, I have to figure out how to get this information from her, or tell her how they need this information. How do I do this?’ Thankfully, I had a check-in the next day. I say, ‘Call the office. These are the questions they were asking me. Heads up: They are very personal.’ So I go for the first question … and she’s like, ‘Hold up, I’ll call them myself and give them the information.’”
–– A.R., an executive assistant

The Boss Who Needed Raw Goat’s Milk Brought To His Private Jet

”[The most ridiculous thing I had to do was] source raw, unpasteurized goat’s milk for his family while they were traveling and having only a couple of hours to find it and have it packed and delivered to the private jet.” –– anonymous executive assistant

The Boss Who Needed $15,000

“‘Hey, can you get $15,000 in cash for my trip to Vegas?’” –– anonymous executive assistant

The Boss Who Demanded Cleaning

“‘Hey, can you clean up the crumbs from my office floor? It was a messy lunch.’” –– anonymous executive assistant

The Boss Who Wanted A Personal Tailor

“[The most ridiculous request was] to sew a hole in his pocket while he was wearing them. He didn’t go change and give his slacks to me; he just wore them and pulled the pocket out for me to sew! If anyone was watching, they’d have called HR for sure! Gotta laugh!” –– anonymous executive assistant

Some answers were edited for style, clarity and length.


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