What’s the craziest thing your boss has ever asked you to do?

The list is endless, from pet messes to shipping the stuff of every ex-boyfriend for the past 5 years back to him. Can’t leave food in the fridge, even with a name tag, without her giving it to her dogs. The worst by far was being asked to hang the new curtains she had just bought in her bedroom only to find a used condom stuck to the floor.

In the evening of my approved personal day. I was relaxing on my couch at around 7:30 pm when I received a text message from my supervisor. He ask that I bring a LARGE microwave bowl for his lunch the next day. Being it was a personal day (he approved) I ignored his request. During lunch the next day somehow he found a bowl. Not another word was mentioned about it.

As a teen I worked in a bakery. The owner was a big gambler, and a woman came in one day with a sob story asking to borrow money. He gave her a loan, but was uncomfortable because he barely knew her. A week went by and then he started sending me to the OTB to see if she was in there gambling. I was 17! He’d say, “It’s slow. I’ll cover the cash register.” But once I missed the bus from the city and called him to give me a ride home. He did.

Do her daughter’s project … she was a junior in college at the time.

At least you had the housekeeper give them to you. My boss had me go to her house and get her favorite underwear out of the drawer and fed-ex them to her at the conference she was at. There are too many to list but this is the one I get teased about the most.

She had been hospitalized for a few days. She didn’t have a ride home from the hospital. I don’t know where her friends and family members are!! SHE asked me to pick her up from the hospital, stop by the pharmacy to get her prescription filled and take her home. We are NOT friends – I work for her!!

She had been hospitalized for a few days. She didn’t have a ride home from the hospital. I don’t know where her friends and family members are!! SHE asked me to pick her up from the hospital, stop by the pharmacy to get her prescription filled and take her home. We are friends – I work for her!!

I have done many crazy things for more than one boss. An eye surgeon I worked for (as a transcriptionist, first, and personal assistant, second) definitely takes the cake. Following is a sampling of my “duties.”

1. Got a change of clothes for him from his home/bedroom.
2. Delivered his many vehicles to and from work, home, repair shops, etc.
3. Paid all of his personal bills.
4. Put money into the bank accounts of his six grown children.
5. Ordered his clothing, including silk boxer shorts (I submitted my resignation shortly thereafter!)

Go to the pharmacy and pick up his Moviprep solution for his colonoscopy. This was after setting the appointment and talking to the doctor about the instructions. At least I didn’t have to mix it for him (that he had to do at home, obviously). No boundaries!

Ewww!

The craziest thing my boss ever asked me to do was to go to the hardware store and pick-up a power drill and a certain size of screws, nuts and bolts. I then had to take the drill and supplies to his home and help his wife put together a bookshelf they had just purchased.

In her last job, my coworker had a little kitchen in the office, and since it was getting expensive taking clients out, as an AA she was instructed that she had to cook for the clients. She told her boss she didn’t cook and they got her a recipe book and told her to follow instructions. She had to go out to buy the ingredients, cook, serve, and clean. And when the “boys” had an evening gettogether in the office after work, she was left with a mess to clean the next day.

On top of being their executive chef, waitress, and maid service…they made her a carpenter one day to help demolish the bosses’ old home and operate a giant excavator. They’re lucky she was smart enough to figure out how to operate the machine and not to knock down the new house. She was also smart enough to get out of there to come work for us.

In her last job, my coworker had a little kitchen in the office, and since it was getting expensive taking clients out, as an AA she was instructed that she had to cook for the clients. She told her boss she didn’t cook and they got her a recipe book and told her to follow instructions. She had to go out to buy the ingredients, cook, serve, and clean. And when the “boys” had an evening gettogether in the office after work, she was left with a mess to clean the next day.

On top of being their executive chef, waitress, and maid service…they made her a carpenter one day to help demolish the bosses’ old home and operate a giant excavator. They’re lucky she was smart enough to figure out how to operate the machine and not to knock down the new house. She was also smart enough to get out of there to come work for us.

In her last job, my coworker had a little kitchen in the office, and since it was getting expensive taking clients out, as an AA she was instructed that she had to cook for the clients. She told her boss she didn’t cook and they got her a recipe book and told her to follow instructions. She had to go out to buy the ingredients, cook, serve, and clean. And when the “boys” had an evening gettogether in the office after work, she was left with a mess to clean the next day.

On top of being their executive chef, waitress, and maid service…they made her a carpenter one day to help demolish the bosses’ old home and operate a giant excavator. They’re lucky she was smart enough to figure out how to operate the machine and not to knock down the new house. She was also smart enough to get out of there to come work for us.

In the 1970s I was the assistant to a manager who turned out to be a sociopath(I didn’t know it at the time) who had no respect for personal boundaries. He called me at my home at midnight from an out-of-state location. This was before the days of answering machines, and I picked up the phone, thinking it was a family emergency. After all, who would call me at midnight? He had decided not to pay his hotel bill and wanted me to “fix” things. As I handled all expense reporting, I was able to “fix” things, but shortly thereafter I transferred to a better job (with a promotion) to another division of the company. This man was able to sell snow to the Eskimos. He would get a job and then after a year his superiors would give him a year to find another job because they were too embarrassed to admit that they had made a mistake in hiring him. I think life finally caught up with him: his wife divorced him, and when I saw him on the street about 15 years later, he looked really beat.

My boss on maternity leave (with twins) asked me go by the pharmacy on my way to work, purchase some items she needed for the babies and bring it to her home. She lived 15 miles opposite my route to the office. When I arrived at her home, she asked me to stay & watch the babies while she took a shower and ran a quick errand.

I once was an assistant to the owner of a large company who would take his dog everywhere he went, because the dog could not be alone and the owner would not crate him. I had a chaise lounge chair in my office for the dog (110-pounds) to lay on the days he was there. We moved into a new office building and I had to paint my office walls ox-blood red because that was the dog’s “favorite color”. It was a beautiful once decorated, but strange because everyone else’s office was neutral.

I had to take the dog out three times a day and make sure he didn’t pee on anyone (he would pee on people he didn’t like). I also made several day trips with the owner and the dog to different stores on their private plane to make sure the dog had someone to be with at all times.

I love dogs, but this was a little much. The job paid well with excellent benefits, so I put up with it until I got enough experience to get a better position.

The oddest thing I ever did for a boss was to go around to several grocery stores and price eggs, on company time! I worked in a sales office for a major company that was coming out with a new breakfast line that included eggs. They were trying to figure out the best price for the product to be cost effective.

I once worked as an admin to the vice-president of a telemarketing company. I was told to clean the BUGS off the ficas plants!!!! I was only 18 years old and did what I was told. Unbelievable.

Jo – Makes you wonder if we didn’t work for the same boss. 🙂

My boss called me from Italy (I was in the US) so that I could call a restaurant in Italy to make a dinner reservation for him. Wouldn’t it have made more sense to have the hotel concierge in Italy do this?

My boss needed to submit an application for a promotion but it was an electronic application and he didn’t know how to work the system. I had to come back early from vacation to fill out then submit his application. When I tried to call him to get some information that it requested, he said he was too busy and to just figure it out.

I once worked for electrical/roofing company ran out of my boss’ house. One time he left his address book in his bedside drawer and I had to run upstairs, get it, and disregard the “Adult ” items that were in there with it. His words. Also, one day I had to run to the bank, write a check to myself, cash it and give his “Massage Therapist” the money. I quit short thereafter.

I worked for a Sr. VP and he wanted me to purchase a bottle of Jack Daniels, wrap it, and deliver it on his behalf on New Year’s Eve to a millionaire friend of his in the hospital who had recently had a stroke. The old guy’s room had so many flowers I thought I was at his funeral, so I guess Jack Daniels was a good gift to give.

Another time, he wanted me to research the location of a WalMart in the Bahamas for his family vacation and call in advance to make sure they had a certain brand of diapers, so he wouldn’t have to pack them when he and his wife brought their 6 mo. old on their trip.

My boss had to leave early one day and wanted me to speak to the nurse at his doctor’s office to get his vasectomy instructions for the next day. The nurse thought it was strange that he ask his assistant to get the instructions considering it was so personal. I then emailed the instructions to his home.

Several jobs ago, I worked for the CFO of a software company. He asked me to go out to the warehouse, and construct a model of everything in the warehouse, including shelves, boxes, etc. with colored paper, and to scale. When I finished this project (??) I turned it in to him. He glanced at it and said, “Very nice. Thank you,” and promtly TOSSED IT IN THE TRASH. I quit the same day…

I typed up high school English papers for my boss’s son. They had to be “perfect” – certain margins, format, footnotes, etc. This was in the pre-computer days, when I had to use an electric typewriter. I stayed late many hours doing this on more than one occasion, and was so glad when his son finally graduated! (He went on to become a doctor.)

I’ve had a few in my career.
1. One boss brought in his Christmas purchases and wrapping paper and asked me to wrap all of them for him.
2. Another boss wanted me to do his personal taxes. I managed to gracefully back out of this one.
3. The strangest request was from a boss who wanted me to put prescription eye-drops in his eyes three times a day after his cataract surgery.

I had a boss do the same thing, but her dog wasn’t house/office broken.

I too have had to “moonlight” as a seamstress. I worked for a partner in a prestigious firm who split his suit pants when he bent over his desk. He asked me to sew them and handed them to me from the crack of his office door!

I had the same experience with a Vice-Chairman. Entered the office cup in hand every morning and put it on the edge of my desk which meant I was to get his coffee. And that was only a little over 10 years ago!

My VP asked me to call the chauffeur and ask him not to drive in the outside lane when he crosses over bridges in NY because it makes her car sick and to also ask him to bring a barf bag just in case she had to throw up!

One boss I had expected me to check his pencils daily to be sure they were sharp enough. If not, I was to sharpen them but to the correct size for his hand. If he deemed the pencil too small, he would give it to me and nastily tell me to save it for my children. (I was not married and had no children.)

I worked for a very small publishing company, and I worked very closely as a “gal Friday” for the owner. He and I got extremely casual in our relationship, which I liked a lot because it made me feel more comfortable. Until, that is, he bit into a tootsie roll, made a face, then threw away (by spitting) the tootsie roll. I watched him move his tongue around in his mouth, and then he looked at me – seriously – and said, “hey! I just lost a filling in that tootsie roll. Take it out of the trash and dig it out for me so I can take it back to the dentist.”

I said, “That is Not Going to Happen. I’m sorry.”

But I still love the guy.

I had a boss that was leaving on an overseas business trip and needed me to go to the mall to pick up a few things for the trip. One item was a package of underwear. He told me to stop at his home and the housekeeper would have a pair of underwear for me to take with me to the mall so that I was sure to buy the correct ones.

Right in the middle of year end tax prep….I had to stop and order heating oil for the boss and his son’s home while the receptionist plays computer game.

I worked for a bank president who broke his upper front tooth on a piece of peppermint the day he was going to speak at a Chamber of Commerce meeting. He had me help him stuff tissue between his upper lip and his teeth so he wouldn’t glue his lip to his tooth as he used SUPERGLUE to repair his tooth! Seriously! It happened…

I had a boss about 10 years ago who would have his personal tailor come into the office and while they sipped tea at the marble conference table, I held up bolts of fabric for them to view. This same boss also asked me to return an automatic nose hair clipper to the manufacturer. Apparently it didn’t work well because it was obvious it had been USED! GROSS!

Ride an elephant. No kidding! I worked for a Shrine Temple and at their fund-raising circus he asked me to ride an elephant with his wife while he took pictures.

OMG…that’s hillarious! Did you tell him you’d get to it right after you put the steel toes on your high heels?

Hey Kristi,
My first job with a large corporation the boss asked me into his office and gave me $20. asked me to go the cafeteria and buy sodas, tonics, etc. when I returned and handed him the items he then asked the employees (one at a time) as to what type of cocktail they would like (his bottom drawer of his desk was filled with airline alcohol bottles (you name the brand he had them) We were all stunned and just accepted the soda! He then was very mad at those who did not imbibe! He was let go that year.

One boss (that had been recently hired as Pres.) requested that I order lots of alcohol for the company Christmas party because he wanted to see what everyone acted like when they were drunk so he would know ‘what kind of people they really are’. Well, that told me all I needed to know about what kind of boss he was… I left the company not long after that conversation for various boss-related reasons and (surprise, surprise) he no longer works there either now. Hmmm…wonder why… 😉

One of my bosses (a doctor) brought in letterhead from every college where his daughter had applied. He had me write one or two line scathing rejection letters from each one of them (i.e. “You MUST be joking”…)- as a joke – and send them to her.

I was working for an insurance company and we had a bomb threat called in that day. My supervisor at the time asked us to do a sweep of the office to look for “anything suspicious looking.” I politely declined and phoned the police department.

We were going through a government audit and my boss asked me to go buy him a pack of cigarettes…he doesn’t smoke!

My boss, who was the president of a company, asked me to take a Johnny Mathis record album cover to a tailor and find material the same as the jacket Johnny was wearing on the album. I never found the material!

I formerly worked for a group of surgeons. One attending had me bail one of our residents out of jail. Two of them had me call them on Sunday evenings to remind them of Monday morning appointments. One female surgeon I had worked for had me meet her insurance appraiser for some damage to her car, and arrange for babysitting when the Nanny was sick. Another had his wife come to me to sign his name to legal/financial documents. I could go on and on…

I worked for the President/Owner of an ice rink. He was very particular about his building and I remember one day he took me around and we picked gum out of the carpets with a set of keys.

There are so many! A former boss who ran a business from his home asked me to shave his neck before he left on a business trip. He also wanted me to hem his pants once. I had to call the school for his kids & tell them they were sick many times. On a regular basis, I had to pick up his dry cleaning. I frequently had to clean up dog “accidents” on the carpet and clean the house. Once the dog came running into the office with a used condom in his mouth! He would even try to carry on a conversation while I was in the bathroom! Those are just the things I remember and I know there were many more odd requests. Needless to say, I no longer work for him!

oh and also, for his friend, he sent a photo of his head to a cell phone and me and another girl at work had to pick out his eyeglasses just by looking at a tiny photo on my phone! There are measurement needed for this and everything! If anyone has purchased eyeglasses before they should know how difficult this was 🙂

My boss has for the most part been reasonable. At times he asks for personal favors but rarely. I guess it is not very crazy, but he preferred that instead of having his annual 401(k) papers notarized at the bank, because that is too inconvenient for him, I had to apply, get letters of recommendations, be sworn in by the court, so officially I am now a notary public! All to save an annual trip to the bank. I can’t complain though because it is something I can put on my resume, but I still can’t notarize my own documents, so off to the bank for me 🙂

Drop off a urine specimen to his doctor; buy clothes for his 80 year old mother without her;

When I first started my job, my boss’s son was in the hospital and I had to go deliver his backpack to him at the hospital. I didn’t even know this person. Then I was asked to wake him up if he was sleeping so he knew I was there. Whatever! I delivered the backpack while he was sleeping and left. How awkward!

I once had to leave work to go get a prescription for my boss. And to make things worse, he gave me his credit card to use to pick up the prescription and when I went through the drive-thru window, I was asked to verify his home address and phone number (which I couldn’t remember). I had to call him on his cell phone to get the information, but felt very stupid. I felt like the drug store was thinking I was trying to take someone else’s prescription. Totally uncomfortable feeling. I was not very happy. Not to mention, we’re not even supposed to run personal errands on company time (corporate policy).

The craziest thing I would say is that I was asked to schedule my boss’s mammogram.

Years ago when I was an Executive Assistant for a young up and coming VP, the President of the company found out that she had bought a dog and he wanted me to throw a surprise party for her dog. I had to call her husband and have him take time off his job to bring the dog to the party.

Guess what I did? I threw a surprise party for her dog and it was a darn good party too… the dog and everyone else loved it.

I guess the way I see it is, if what is asked of me does not compromise my morals and values then okay. But if it does, then I have a decision to make.

There is nothing wrong with someone asking me to do something, its up to me to decide how far I would go for a job.

He asked me to drop off his pet’s stool sample at the vet’s. And dropped off the container on my desk while I was having lunch. Ugh.

A new assistant manager had been hired and was moving here from out of state. Rather than the company paying his moving expenses with a professional mover, they used one of the company semi trailers. Several of us male employees were forced to go to his new house and unload everything off the semi and move it all into his house. Basically, we were forced to be his moving crew.

Here are some: my boss spilled a drink on his shirt. Unfortunately, he had a very important meeting that afteroon. I had to go to the store buy him a shirt and have it pressed and brought to his office in time to make a great presentation.

On another occasion I had to go to the costume shop and pick him out a costume for our Halloween party.

From a co-worker. Her company relocated and she had to meet the movers at her boss’s new home, make sure everything arrived correctly and had to instruct the movers on the placement of the furniture. She has never been to the house before.

One morning, my boss called me from her home. She was hysterical. She had a mouse in her home, and was petrified. She could not move to get ready for work. I went to her home and tried to catch the mouse (to no avail). I stayed with her until she was ready for work. The next day the mouse came back and another co-worker went there and caught the mouse – Thank God!!!

The strangest request I have ever received is when my new boss arrived in town and asked me to go looking for an apartment for him to stay in temporarily. That wasn’t the worse part of it . . . it had to be the perfect place for under $50.00 a night . . . You can’t even rent a room at Motel 8 for that cost!!!!

My boss called while driving her car and asked me to figure out where she was using a state map. She told me which county road she had just passed and which highway she was on.

Our building was in a commerce park, which was pretty much deserted after 5:00. Since I didn’t have keys to lock up, he asked me to wait outside our building, in the dark, alone (after everyone else has left for the day), with a handful of checks to give out to our sub-contractors who would be coming by to pick them up. Needless to say, I refused, and he had someone with a key stay with me.

A couple of years ago my boss held an offsite staff meeting at his cottage. After lunch, he offered a pontoon ride and water skiing so we all changed into our swimwear. We were about to launch the boat when my boss bent over and had me spray sun guard on his balding head. I got teased about that one for quite a long time!

I was asked by a Phoenix orthopedic surgeon to drive to his home, pick up his Ferrari, gas it up, take it to the service shop, wait for it and then drive it back to his home. He was as arrogant as they get.

1. Pick out (but she went and bought them), and wrap the Christmas gifts she was giving to her team, including mine. She was just so busy on some special projects, she didn’t have time to do it, and I didn’t mind. The night of our Holiday Party, when she gave a thank you speech to everyone for their hard work throughout the year, she told everyone what i had done for her. They teased her about it for the whole next year. She never asked me to do that again : o ).

2. One day she had to work, but her children were out of school due to a bad storm. She couldn’t get a sitter, so she brought them to work with her, and asked if I’d mind watching them.

My boss asked me to go to the store and buy him shaving cream and razors because he forgot to shave the night before……when he was at home!

Watch for his ant farm to arrive in the mail and set it up for him while he was out on vacation. I hate bugs!

To call around for a used toilet to replace a broken one in one of his rental houses. I could not keep a straight face when a vendor would answer the phone and I said, “Do you have a used toilet for sale?”

To stay late on Christmas Eve and wait for a personal package to be delivered; something he purchased for his wife for Christmas!

I have two short ones:
1. Pick up the boss’s coffeemaker that his wife had taken in for repair. The repairman was telling me what was wrong – I didn’t have the heart to tell him I didn’t care.
2. Another boss (male) had just gotten his ear pierced. He had to take it out for a business meeting. After the meeting, couldn’t get it back in. I put it in for him.
Unusual requests – a day in the life. . .

Here’s another one. To cut the tag out of the underpants she was wearing. Considering her age and personality, this was not so much horrifying as it was “Gee, how do I graciously bow out of This one?”

Scrapbook pictures on company time. We had a lot of pictures of firm events and I got to shop for scrapbooking stuff and I made a scrapbook to be used for displays for career-day and other events. I also helped type, proof and correct homework for a bosses son.

Several years (and bosses) ago, my boss gave me the first and last names of her aunt and uncle, who lived somewhere in Florida. She wanted me to find out where they lived, and then have flowers sent to them. It was Valentine’s day! I did it, but it took me a whole morning and many, many long distance phone calls. I live in Northern Ontario.

Drive a forklift and pick up some large boxes in the warehouse located in the back of the office.

I was once asked to have a menu from IHOP professionally framed and an engraved plaque was added to the frame that said “Come intoxicated… Leave stuffed”.

Create travel vouchers for trips that were never taken. Little did I know the facility was possibly going to be audited and he got wind of it. I didn’t find out until two years later. I felt duped. He’s now serving time.

ha ha ha…. OMG! watch out for the tomatoes!

Back in “the day” I worked as an Admin Asst for a steel pipe company for the VP of Sales. He would walk out of his office, without a word set an empty glass on my desk and that meant he wanted a glass of water…and the kitchenette was RIGHT NEXT TO HIS OFFICE! We’ve come a long way baby!

Bring his dogs to be groomed (and pick them up).
Order new checks for his wife’s checking account.

I’ve worked for several executives, and here are some highlights I could remember.
1. A VP asked that I sew his jacket tear up for him, and a button on another one.
2. A President of company asked that I give money to the building engineer who wanted to by tools from a guy on the street that was selling them for a good deal with the price tags still on them from some of the leading stores. (told him no.)
3. A President of company expected me to wash out his mug and lunch dishes and utensils daily. I was not allowed to throw out the plastic forks even if one prong was broken off, because it was still usable.
4. A CFO wanted to set me up with her brother.

My first week at a new job…very different from what I had done previously. The Vice President (my bosses boss) told me he would be out of town for a week and wanted me to totally reorganize his office while he was gone-every cabinet, drawer and file…talk about a trial by fire! Everyone else in the office was as surprised as I was but he was very pleased with what I had done and I learned more than I ever thought I would in that week!

Walk her dog and pick up what’s left behind. I didn’t mind because I love dogs!

1. Remind him when his children’s birthdays are and buy their presents.

2. Open his sandwich everyday to make sure there were no tomatoes on it.

One of the craziest things I think I have ever been asked to do: Pick up a boss’s daughter from school (elementary), then pick up some cheese coneys on the way to dropping her off at home! Oy Vey! He needed a nanny, not an Admin. Assistant! (By the way, he was truly one of the worst bosses I have ever had, to date)

Cut out clouds. No explanation regarding what it was for, size and color didn’t matter. Just, make some clouds and cut them out for me. Ok, boss, whatever you want….

The craziest thing that my Boss has ever asked me to do was….”Take a break!”

My boss wanted me to figure out what happened and fix his wife’s car that was sitting dead in a parking lot clear across town.