Tales From The Front Desk: The Painfully Ridiculous Things Office Managers, Admins, and Executive Assistants Deal With

If you’re an Office Manager, Admin, or Executive Assistants, you probably get a million requests a day.

It makes sense. These roles have always been demanding, and today they’re more important than ever before.

You’ve proven yourself to be a problem solver. You devour the most impossible tasks with vigor, and you enjoy a challenge.

But the more we work with and learn about all the people in these roles, there’s one skill that continues to amaze us:

Your capacity for dealing with ridiculous situations.

Specifically, questions or requests that make you want to go…


We didn’t realize the extent of this phenomenon until we launched our SID video for Administrative Professional’s Day. Although tongue-in-cheek, our parody about an Alexa-like device that shuts down crazy requests clearly struck a nerve.

It turns out, truth is stranger than fiction. As soon as we hit publish, we got tons of examples from our community of EAs, OMS, and Admins. And their stories were way crazier than anything we could come up with.

(PS – If you’re an Office Manager or Executive Assistant, join one of our private FB Groups (Office Managers click here, Executive Assistants click here). Each group is a place to connect, collaborate, and share advice on how to overcome the wide spectrum of challenges you face in your role.)

So without any more preamble, please enjoy the best of the best – the weirdest, most vexing, downright ridiculous tales from the front desk that we’ve heard so far from our community.

Just be glad this wasn’t you!


Hill of Beans

Our first example definitely had us laughing out loud.

This is a great illustration of the way professionals in these roles are sometimes tasked with projects that aren’t the best use of their time or their skillsets (to put it mildly).

“I worked for someone that really liked Wendy’s chili, but without the beans. It’s mostly beans. So at least once a week I picked the beans out of chili.”


Anonymous Bean Picker, this person clearly didn’t deserve you. (I hope you left at least a few in there.)


The Crossing Guard

Here’s one from someone who found herself performing a task that was definitely outside her scope of work. (And while we know it’s not polite to laugh, the visual here is priceless…)

“Our office building is located in between a school and their athletic fields. There are signs in the parking lot that tell people not to use the parking lot to cut through to get to the athletic field, but of course it is ignored.

I was asked to stand outside with a sign that tells people not to use our parking lot so that our employees could get out of the parking lot faster and without a traffic jam. In all honesty, the ‘traffic jam’ consisted of maybe 10 – 15 cars. (It’s a small private school.)”


But that’s not all. She also told us about a request from the same boss that had her playing amateur dietician.

“I have also been asked to create a menu for each catering event with a list of all ingredients from the variety of caterers we use to identify how many calories are in each serving. They felt this would help people that are watching what they eat maintain their diet (have they heard of Google?).”


Just Google it, people!


So Fresh and So Clean, Clean

Check out this question from one particularly proactive (and hygienic) colleague:

“I’ve taken the mouthwash out of the bathroom because it seems I am the only one using it. May I keep it?”


Yes. Yes you can. Now step away from the desk.


Not to Be Difficult, But…

An Office Manager submitted the following exchange:

Employee: “I need lunch for a meeting.”

Me: “Ok.’

Employee: “I am Paleo, Tony is vegan, Sarah can’t have gluten or dairy and then Bob’s on a cleanse. What are my options?”

Me: “Air and water sound good?”



Batteries Not Included

Here’s an Office Manager with an all too familiar situation.

Coworker: “We’re out of batteries”

Me: “Did you check the drawer that says ‘Batteries’?”


Coworker:“Found them”


It’s always the last place you look, right?


Next to My Lunch??

Norah also told us about this creepy-crawly question from her boss:

Coworker: “Did you happen to throw out a tupperware in the fridge with worms in it?”

Me: “…”

Coworker: “I was gonna go fishing later.”


In the office fridge, though? Not cool, man. Not cool.


The Ice Machine

According to Karlenea, this was “the strangest phone call I have ever ” Here she is calling a local golf course:

” ‘Hello, you have an ice machine at the bathroom between the 4th and the 10th holes. I need to know what brand of ice machine that is. Can you help me?’

That was officially the strangest phone call I have ever had to make on behalf of a CEO.

My CEO is super fun and we were all laughing over the need for me to do this. He took a photo but couldn’t find it so this was the option.”


Noah’s Ark

“I [once] had to get live animals on stage for a presentation.”


We’re dying to know what this presentation was about.



Here’s one from someone who told us that the higher ups in her office have a terrible habit of asking for personal items like aspirin, Kleenex, or candy/gum. But there’s one request that takes the cake:

“My executive asked me to borrow money. WHAT?!”


So wrong.


When in Doubt, Blame the Curb

Here’s one more from our pal Emily:

“I was asked to contact the property management company to have them repave a curb because this person hit the same corner of the parking lot twice popping the tires on his BMW. The curb is not as rounded as other curbs in the parking lot but it has been here for 30 + years.

One would think that if you hit it once you’d learn, but a week later he did the same thing and popped the tire again.”


Sounds like the better solution would be for your boss to, I don’t know… not drive on over curbs??? We feel your pain, Emily.


Nope and Nope

An Executive Assistant dropped these two gems on us. She had a boss who asked her these two questions on separate occasions:

“Can you get the gum off of my shoe?”

“Pack up my gun safe before you leave!”


Not sure which we’d rather hear…


The Dreaded Coffeemaker

Employee helplessness was definitely a prominent throughline in the stories we heard. Sometimes the most capable of our colleagues seem to be utterly incapable of performing the most mundane tasks.

For some, this phenomenon seems to revolve around the coffee maker.

“I think the silliest questions I get are about the coffee maker:

How do you fill the bean container?

It says add water, how do I do that?”


Ah, coworkers… they never cease to amaze.


Transportation Woes

These challenges prove that there isn’t much that a good admin pro can’t accomplish.

“I had to get a police escort for my boss to get him through traffic. No really…

I also had to get a co-worker to FLY to another state to meet my boss’s wife to get his passport that he left. I had to get him a VISA to India in four days, so we were in crunch time to make it happen. I did it too. Nothing short of a miracle.”



Casual Mail Fraud

Here’s Norah again with her boss nonchalantly asking her to commit a federal crime. (No big.)

Boss: “Will you ship this wine to our client?”

Me: “I think that’s illegal.”

Boss: “Just say it’s grape juice.”


What could possibly go wrong?


My Best Friend’s Wedding

Another Executive Assistant had this story for us:

“My boss had me research average temperatures and humidity in August between 4 pm and 6 pm in the Hamptons to figure out best time to begin her wedding. I called a weather org at Cornell University and got 3 years of historical data from a nearby airport to compare in a spreadsheet.

The result: not much difference!”


(Let’s pause and appreciate how impressive this is…. Nice work, Meghan! Ok, moving on.)

But that wasn’t the end. Far from it. Her boss also had her:

“Send Thomas the Tank Engine party decor to be printed, pick it up, cut it out, deliver to her home for her son’s bday party.”

“Reschedule foot doctor appointment.”

“Call W Hotel to change the fragrance in the ENTIRE hotel.”

“Make sure car service to airport does not have a strong odor.”


And then there’s this:

“No one in office was allowed to chew mint gum because of the smell.”


She eventually had enough.

“I had to quit her and transition to someone else at the firm. But now we are really good friends!!”


All’s well that ends well, I guess. Just don’t chew gum around her, Meghan. We hear she doesn’t like that.


Emergency Surgery

Sometimes you have to do whatever it takes to help a teammate out of a jam. Here’s a funny story we received:

“At the time I was working in a sales office for a major book manufacturing company.

One of the salesmen was heading to probably the biggest meeting of the year with his largest client and had a tear in his pants in an embarrassing location. Luckily the damage was spotted before he left the office.

He had another salesman follow him to the men’s room where he removed his pants and sent them out to me to repair. Later on he told me that his wife didn’t know how to sew but he knew I did.

Guess it isn’t always the best idea to let ‘some’ people know what you like doing off the clock!”




Sometimes the bathroom can be a source of drama for the office. Here’s a story that proves the point:

“As an Office Manager I get a lot of requests that concern behavior of coworkers. Some of these are very valid but some border on being ludicrous.

One in particular had to do with a past employee who got mentally stressed at the thought of coworkers using the bathroom. Her office was not far from the only bathrooms in the office and she didn’t want anyone using those bathrooms but instead to have them go outside of our office to where the public bathrooms are in the office park.

I was concerned that it was things like foul odors coming from the bathroom and she said no that wasn’t it. It was just that she knew what they were doing when they went to the bathroom (as in relieving themselves) and that thought just grossed her out.

I offered to move her to a different location that wasn’t as close to the bathroom because I can’t tell employees to either not go to the bathroom or to go outside in the elements and walk 7 minutes each way each time they required the facilities.

I ended having her close her door so that she wouldn’t see people walking past to go to the bathroom, and got a sound machine for her office so that she wouldn’t hear co workers walking past. In addition I got air fresheners to position all around the building so that if someone used the ‘poo-pourri’ in the bathroom the smell wasn’t as obvious.

The employee still wasn’t that happy with the arrangements but I could see no other solution.”



Maybe They Use Slack?

One Personal Assistant told us a story that raises the question, What exactly have you been doing this entire time?!

“Someone had been working at the company for a month and asked me what his email was.”



Helpless Part Two (Electric Boogaloo)

A Vibe Manager with a scenario I’m assuming a few of you have dealt with before:

“One time my coworker asked me to come to their house to plug their phone in the wall.”


I guess… it’s nice to be needed?


Needle in a Haystack

“My CEO returned from a trip with photos of a random stranger’s luggage and asked me to purchase one just like it. No photos of the label or anything, so after hours of pouring through Google images, I found it!”

Color us impressed.


Helpless Part Three (Pencil Problems)

“When I was first starting out as a Girl Friday, the office manager called me into her office as she needed someone to put lead in her mechanical pencil. She couldn’t figure out how to do it.”



Taste the Feeling

“My boss asked me if I could reach into the cooler and get him a Coke so he didn’t get his hand wet.”





One Executive Assistant reminds us that sometimes having to cover for your boss means stretching the truth a bit.

“I’m leaving early today because I have to go to a football game. But if HR is asking, my cat died.”


10 bucks says Kelley’s boss didn’t even have a cat.

Dumb Phone

“I had a boss email me two addresses along with detailed instructions to go on to Google, click maps, enter in the two addresses, and then email him the directions. He sent me all this  using his smartphone.”



Problem Solved

“I would have to print out documents for my boss’ manager whenever he was in town. Someone sent him an email and he wanted the attachment printed out before he left on his flight back to Florida. I printed out an attachment that was 11” x 17”. He yells at me, ‘How am I supposed to carry THAT on a plane with me?!! It’s too big!’

“I kindly folded it in half and put it in his folder.”



Make it Rain

“I was asked the precise time of the forecasted rain. My boss was concerned about his son’s little league game. I picked a time out of the air and said ‘4:00 pm.’ At 3:50 pm clouds rolled in and at 4:01 pm the torrential rains fell.”


Did you ever consider that you actually have a hidden power for predicting the weather? Just a thought.



“A co-worker’s child puked in the company car and I was asked to find a place to clean it.”

– Anonymous


Presented Without Comment

And finally…

Boss: “What time is the noon meeting?”



How do your crazy requests stack up against these? Let us know the craziest thing a boss or co-worker has requested from you in the comments.