A Certain Slant of Light

Posted by Ask a Manager

https://www.askamanager.org/2026/04/the-eye-drops-the-flusher-and-other-ridiculous-requests-made-of-assistants.html

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It’s Administrative Professionals Day! Last week we talked about the most ridiculous requests you’ve seen made of assistants, and here are 17 of my favorite stories you shared.

1. The flusher

This was when I worked at a toxic doctor’s office. I was admin assistant to his wife, the practice manager, and my desk was closest to the bathroom. She always wore a headset and once took a call while in the bathroom. When she was done with the bathroom part, she came out and motioned for me to flush the toilet for her so her caller didn’t hear it.

2. The astrologist

When I was an assistant, my boss made me input every day when Mercury would be in retrograde into her calendar.

3. The prayer

My boss at a legal staffing company once sent me to a church to light a candle of remembrance to honor her late husband, asking me to be sure to pray for him on her behalf. She told me she was too busy to go on her own (I was her EA; she wasn’t) and I heard her explaining to her adult children the heart rending emotions she felt while she lit the candle.

It was my first job out of college and I had a great deference to authority, and so I did it. Even the prayers, although we did not share a religion.

4. The eye drops

I was working at a Big8 accounting firm and for a brief period of time I had to put eye drops in the eyes of one of the senior partners. (Editor’s note: this has apparently happened enough that there were TWO stories submitted of two different bosses requesting this.)

5. The car

When my boss couldn’t park in her preferred spot in the parking garage, she’d leave her car in the loading dock, come inside, and throw her keys on the reception desk. I was supposed to go park her car for her and then, of course, retrieve it again at the end of the day since she didn’t know where it was in the garage.

6. The binder clip prep

I was an admin for three years to the president of a tiny medical software company. I would place office supply orders — pretty normal. But when I ordered new binder clips, I had to dump out the plastic cylinder of clips and flip up the tabs on each one, then put them back (at which point they never fit properly into the cylinder anymore and I had to kind of jam them in). This was because my boss was too busy to do this himself when he wanted to use a binder clip.

7. The mail chute

This happened back in the early 1990s, before there was internet and email. I worked as an assistant to a salesman in a bank and used to wear dress suits and pantyhose to work. My job was to help him put together proposals for organizations. He was a type A personality, and I tried to comply to his demands, even making sure that the paper on which we printed had the watermark consistently facing in the same direction.

One day we had accidentally sent out a proposal with a section missing. It had already been delivered to our mailroom’s DHL bin, awaiting its final destination. I asked why we couldn’t just send the missing section separately, but my boss was worried that it would appear unprofessional. Then he suggested that the two of us go to the mailroom together, where he would pick me up by the ankles and dip me upside-down, head-first into the DHL bin to retrieve the package. He was completely serious. For a second, I imagined this scenario in which my skirt would slide up my thighs. I refused. In the end, we got a couple of the smaller men from the mailroom to recover the proposal for us, so it all worked out and my dignity remained intact.

8. The coffee

This wasn’t so much an unreasonable request, but I was so proud of my sneakiness at the time – I occasionally had to assist a woman who was notoriously mean to everyone. She always wanted Starbucks coffee, but the trouble was that the closest Starbucks was 4 blocks away and always had a huge line (this was before online ordering was a thing), so getting it would take forever. She DID. NOT. UNDERSTAND why her coffee wasn’t magically appearing two minutes after she asked for it.

Finally, after being berated one too many times, I asked the Starbucks barista for a bunch of cups and lids, and from then on, any time this woman demanded her Starbucks coffee, I simply dipped into our kitched, poured whatever Folgers coffee was let in the shared pot into the Starbucks cup, popped a lid on, and brought it back to her. She never knew the difference.

9. The light

My boss once texted me to come turn on his office light while he was already sitting in there.

10. The avocados

The dumbest request I’ve ever gotten as an assistant: going out every morning to buy multiple avocados for the CEO to choose from. After she chose her preferred avocado, I had to slice it in half, put cayenne pepper on it, and serve it to her on a plate. With chopsticks.

She once asked me to put the whole avocado setup on a paper plate in a ziploc bag so she could eat while driving to the Hamptons (again – with chopsticks). I made the more senior assistant handle that one as I didn’t want to be liable in case her dumb ass did something on the road.

11. The trash collector

I worked for a tiny org, with a tiny office space. The boss refused to buy the city’s trash and recycling services because the rolling bins would have to be visible in the main space and that would “look unprofessional.” Instead, multiple times a week I was tasked to take office trash home to dispose of in my own residential bins. I even handled some bulky trash disposal piece by piece from a renovation prior to my start date.

12. The chef

The EA at my first big job was responsible for preparing lunch for the CEO every day. She cooked it at home the night before and warmed it for him (always on the stove, no microwaves allowed) and served it to him at the same time daily. Every other task on her agenda was dropped for lunch. It took at least an hour a day, between prep and dishes afterwards.

13. The rehab driver

I was voluntold to escort the nonprofit CEO’s adult child to rehab. To make matters worse, the adult child didn’t realize that the “appointment” was an intake to a 30-day program. Needless to say, she declined. That was an awkward Uber ride back to the office.

14. The swim instructor

After my first year of law school, I was hired for the summer by a law firm in my hometown as a law clerk/paralegal/administrative assistant/whatever Weird Lawyer needed me to do.

I mentioned I was on the swim team in college. He would swim for exercise a few times a week. I had to give him swim lessons.

15. The sofa

Early in my career, I was part of a small army of assistants supporting the owner/CEO of a reasonably sized company. When I was hired, her office was mid-refurbishment — and she was profoundly offended by how new the leather sofa looked. Apparently, it didn’t align with her carefully curated vision.

To fix this, another junior assistant and I were given a highly specialized assignment: make the sofa look lived-in. How? By taking turns jumping on it in 30‑minute shifts until it met her aesthetic standards.

This was a very professional office. It was the 1990s. The dress code was strict. We wore pencil skirts and pantyhose. Picture two exhausted assistants aggressively bounce-testing a leather sofa like it owed us money. It’s honestly a miracle neither of us pulled a muscle, ripped hosiery, or had to explain to HR why we were airborne in the CEO’s office.

The sofa survived. So did we. Barely.

It was also the exact moment I realized I might want to explore a different career path — one that didn’t involve trampoline-based interior design.

16. The fish tank

Years ago, I worked for the very sweetest, most lovely older man who happened to be very short. He also loved tropical fish, and in his office he had a wall-sized tank that he was very proud of.

One day I heard him yelling my name, ran to his office, and turned the corner to see him standing in a stepstool, in his underwear, soaking wet. This was confusing, to understate it.

Turns out one of his fish had died and he had been trying to use a net to get the body off the bottom of the tank, but couldn’t reach and fell in! He thought maybe I could help because I had longer arms.

Once I got some clarity on What exactly Was Going On Here, I of course happily tried to help, but it was wall sized! I couldn’t get the poor deceased fish either, but I did call the fish tank guy (yes, we had a guy) for an emergency rescue.

17. The refusal

My second day working for a renowned surgeon and department chair (and big muckety muck overall), he gave me his wife’s phone number to assist her with her afternoon social in three days. (Note: attendees were just her friends and social climbing assets.) I was so shocked, my spine grew unexpectedly and I told him that I was a state employee and would never perform any personal errands for him and certainly not his wife. To his credit, he just said okay and never brought it up again. I actually think he respected me for speaking up and the four years I worked for him were some of the best in my work life.

The post the eye drops, the flusher, and other ridiculous requests made of assistants appeared first on Ask a Manager.

https://www.askamanager.org/2026/04/the-eye-drops-the-flusher-and-other-ridiculous-requests-made-of-assistants.html

https://www.askamanager.org/?p=37744