the cheap flights, the bursting jacket, and other stories of malicious compliance — Ask a Manager

Last week we talked about malicious compliance — times when someone purposely exposed the absurdity of a rule by doing exactly what they were told to do. Here are 14 of my favorite stories you shared.

1. The requisitions

I worked for a fairly large, regional bank that covered about three states with nearly 9,000 employees. The CFO decided that everyone was wasting money on frivolous things like office supplies. He mandated that ALL requisitions for any supplies must come through him. ALL OF THEM. This of course held up the process so even getting a needed pen could take over a month. Some of the managers got together and quietly decided to do just that — send him a requisition/ request for every single box of pens, box of paper, box of toilet paper, single toners, etc. One box/item at a time. It lasted two weeks.

2. The jacket

It’s not nearly as maliciously compliant as the teal polo guy, but I had something similar at an office where I worked where we had to wear these (ugly) button-down jacket things so we would all look neat and presentable for clients. It was in the employee handbook that you had to wear the jacket, closed, at all times.

At one point I was pregnant and I knew it wouldn’t fit me much longer, so I emailed HR explaining the issue and asking if I could get another one in a bigger size or if I could stop wearing it. I was told no and no. Ummm. So I kept wearing it, even as it started stretching at the buttons (I wore a t-shirt underneath). Eventually there were certain buttons in the middle I couldn’t button (it was a long jacket), so I left those middle buttons open. I looked absolutely ridiculous.

This lasted until one day in my eighth month, when HR came marching over to my desk to tell me I shouldn’t wear the jacket anymore.

3. The insulin pump

I’m a type 1 diabetic, and I have an insulin pump. It beeps to alert me to issues, but different beeps mean different levels of urgency. After the first beep, I tend to pull my pump out of my pocket and silence it and/or immediately address the issue, depending on the level of urgency. My point is, it’s both lifesaving and as unobtrusive as possible.

My ex-boss Dan knew about my insulin pump, but would often publicly chastise me for “checking my phone” with a weird smirk. Maybe he thought being diabetic was embarrassing? Not sure. His remarks often drew more attention than me just trying to fix my pump, which is obviously not what I was going for. Urgh.

We had an internal meeting once where Dan was extremely strict about no phones in the room, to show our grandboss how focused and productive we were, or something. Because it apparently understands comedic timing, my insulin pump starts beeping halfway through this meeting. Adhering to the no phones rule, I shrug and keep talking through my slides. Beep-beep-beep-beep. My coworkers are starting to get anxious, because they all know (thanks, Dan!) that I should probably be fixing that. BEEP-BEEP-BEEP-BEEP. I finish my presentation. Any questions? Two different coworkers ask me to sit down or if they can get me anything to drink. Someone asks if I need an ambulance.

I’m totally fine – I know my urgent beeps from the non-urgent ones! – but I’m enjoying watching Dan squirm when his boss freaks out that he has coached me to ignore medical emergencies in favor of arbitrarily phone-free meetings.

4. The “accommodation”

My last boss maybe broke the law by telling me I couldn’t work remotely for a few days while recovering from a complication of my disability. It’s an invisible disability and she was a jerk. She told HR that due to the nature of my job I couldn’t be out for consecutive days, which was patently untrue. When they denied my request and instead offered me one additional WFH day per month, I explained that this would be like telling someone who had a mobility issue that sure, they could work remotely for the next month — but only for half of each day. It needed to be consecutive days home for recovery, but I was still able to work. They said to just use up all my sick leave.

When I accepted another job offer, I didn’t immediately put in my notice. I had that sick leave available and, as luck (?) would have it, the fussy nerve in my foot was ever so slightly acting up. So, what did I do? Explained to them that I was experiencing a mobility issue and wouldn’t be able to come into the office until it was better. And darn, I guess I won’t be able to work from home even though it’s crunch time due to their policy. I enjoyed a week off, came back on a Tuesday, put in my notice, and left that Friday.

5. The travel reimbursements

This was many years ago. When traveling for work, I discovered that I couldn’t get reimbursed for customary tips on transportation (taxis, group airport shuttles). When I complained, it was just “too bad.” Only a few dollars here and there, but I was peeved. Why should I be out money while on work travel?

I read the travel policies closely after this and realized I could get reimbursed for car rental and parking. Flying in for a client meeting less than two miles from the airport? Car rental. Spending a week downtown in an expensive city for which I didn’t particularly need a car? Car rental plus over $50/day in parking fees so the car could just sit there until I needed to drive back to the airport.

Did this for all work travel for the remainder of my time there.

6. The write-up

When I worked in a now-bankrupt bridal store as a supervisor, the assistant manager and district manager pulled me into a meeting about receipts that had gone missing from a Sunday in March I worked. They alleged that the whole day’s worth of receipts had gone missing, they checked the schedule and knew I worked / closed that day, and were writing me up. I was appalled, and asked for the date. When they gave it, I said, “Oh, I know what happened!” They didn’t want to hear it. I tried several times, until the DM told me they didn’t want my excuses, but if I had any kind of rebuttal I could fill out a paper to submit with the write-up. I just said OK and filled it out. They made me fax it to corporate myself from the front desk, admonishing me the entire time for my carelessness. Before I pressed send, I asked ONE LAST TIME if they wanted to hear my side. No. OK, off it goes!

About an hour later I was talking to another associate at the counter, the assistant manager standing right next to us. My friend asked what the meeting was about, and I told her. She asked what date that was, I told her that too. She frowned, checked the calendar, then said, “But that was Easter! The store wasn’t even opened!”

“I know,” I said, “but ASM and DM didn’t want to hear it. I put it on my rebuttal sheet, though.” Big smile at ASM as I said it, who looked horrified.

Less than a week later, I was issued an apology from both of them. In writing.

7. The hours

I had an employee get sick and need to go to the ER. I took her, stayed with her, waited until she got checked in, swung by drive through for lunch, and came back to the office. My manager blasted me for taking so much time off of work (about two hours).

So I kept to my 9-5 schedule and cut the extra 20-30 hours a week I had been working. But I sure was in the office 40 hours a week just like he asked.

And then I left and he got fired for not being able to do his job. His career has sunk over the years, with him taking lower and lower positions at each company.

8. The sandwich with “everything”

I used to work at a small mom and pop sandwich shop. We had a lot of options for condiments and toppings. Every single day I’d take multiple phone orders along the lines of “I want a turkey sandwich with EVERYTHING on it.” When I tried to clarify, the customers would often get snippy and rude – even when I politely explained that we had four kinds of mustard, three kinds of mayo, three different hot peppers, two types of pickle, avocados, carrots, olives, and various other things that most people don’t want on a turkey sandwich. Inevitably it would turn out they meant something like turkey with regular mustard, mayo, lettuce, maybe some cheese or tomato. Not even close to “everything.”

On my very last day, one of these rude customers called in yet again and demanded a turkey sandwich with EVERYTHING on it. So I said “Yes ma’am,” and made one. Alas, I clocked out before she picked up her turkey sandwich with EVERYTHING on it.

9. The Spanish speaker

Year ago, I worked for a university that ran a busy healthcare clinic. I was the only Spanish-speaking person in our department. There happened to be a position open and my boss quickly hired the daughter of someone who worked at the university’s main campus. We had begged and begged beforehand that another Spanish-speaker be hired because we served a huge population of Spanish-speakers. If I was out sick or something, the clinic was screwed. So this gal gets hired and my boss says that she speaks Spanish! Great! It’s on her resume and everything.

I introduced myself in Spanish and tried talking to her a couple of times. She responded with kind of a non-committal “si” or mumbled something and pretended to be busy. My spider-sense went off. I asked my boss and she assured me that the new person speaks Spanish.

“Are you sure? Because she doesn’t…”

“I’m sure!”

So … I started forwarding about half my Spanish-speaker calls to her phone and started calling her to the front desk to help with interpreting. It only took about a week for her to angrily admit that she doesn’t actually speak the language.

10. The overshare

At the Big Bookstore, our (nitpicky) district manager one day decided that the Information kiosk should never be left unattended. Not for one single second. On my first day back after a super-fun bout of food poisoning, I was assigned to the kiosk. I had to make a break for the restroom at one point, and returned to find the district manager, the day manager, and a line of about three people. Rather than helping the line, the district manager demanded to know — at the top of his lungs — why I was “abandoning my post and ignoring the needs of our valued customers.” Not quite at the top of my lungs but still very audibly, I said, “In the future, I will remember it’s preferable to vomit in the kiosk rather than leave it unattended. Can I help the next customer?”

Surprisingly, none of those customers needed my help after all, and I got to go home early that day after the red-faced district manager left.

11. The flights

I used to work for a major multi-national company in a division which did engineering work for ships.

Headquarters came out with a rule that we always had to book the cheapest possible flights if we had to travel for a job. Most of us booked sensible flights, ticked the “out of policy – business needs” box and carried on as normal.

One of the service technicals was booking flights for a job and found the cheapest option offered on the travel booking system was some crazy combination of five flights, via places like Istanbul and Amsterdam.

He promptly booked the flights, spent three days in transit, and by the time he got to the dockyard the ship had sailed.

He was very smug about it.

12. The physical

My job involves some pretty physical field work, so we have to go through annual physicals for insurance purposes. Kind of a hassle, but whatever. Except for a few years ago, when a new staff doctor took over administrating the physicals and approvals, and anyone with any kind of psychiatric prescription got phone calls asking extremely detailed, frankly invasive questions about their medication, medication history, symptoms, how well each medication treated your symptoms, your side effects, the list went on – and if you’ve ever been prescribed anti-depressants or anti-anxiety medications, you know that you usually have to try out quite a few to find the right fit. It became quite apparent that this person did not want to approve anyone on any of these medications for field work, which was about 70% of our job description.

I got my call on a Friday afternoon, about 10 minutes before the end of a shift that started at 3:45 am. I was beyond over it. I was over EVERYTHING. I was so far over it I had broken through the atmosphere into a peaceful void of zen and mild heat exhaustion. The new doctor started out asking questions about my experience with Zoloft, which I had taken for six weeks over 20 years ago. I asked why that was relevant. She said it was important information to assess my fitness for field work, tell me about the side effects you experienced with Zoloft. I said, “Oh, well if it’s important information–” And then I became an unskippable cutscene.

I experienced a lot of side effects with Zoloft. They were … gastrointestinal in nature, and I spent 40 minutes describing them in excruciating detail. I invoked all five senses and every colorful metaphor my sleep-deprived brain could come up with. Every time she tried to break in, I just said, “No, no, I want you to have all the information you need! It’s important!” When I finally ran out of steam, she decided we didn’t need to discuss the rest of my medication history. I went home, slept for something like 11 hours, sent an email to HR asking for clarification on why the staff doctor was asking about my full medication history, which wasn’t in my employment physical paperwork, since I hadn’t signed any releases for the rest of my medical records, and went back to bed.

On Monday, I was informed I was cleared for field work. It was a different doctor administering physicals the next year.

13. The $20

My company uses a travel agency’s booking platform that invoices departments directly for costs. However, it doesn’t allow conference-rate bookings, which require going directly to the hotel’s website with a special code. So, employees can book outside the platform—but only if they’re willing to float the cost.

On my first work trip, I booked a conference-rate hotel using my own card to save the company hundreds. My flight home wasn’t until evening, so I paid a $20 late check-out fee to work from my room instead of squatting in the loud hotel coffee shop. A month after submitting a reimbursement request for the travel charges, my entire request was denied because late check-out was “not a required business need.”

Cue frustration: I’m now floating over a grand on my card for hotel charges because of a $20 fee.

Determined, I enlisted ChatGPT to draft a multi-page thesis proving that $20 was, in fact, a legitimate business expense—complete with productivity analyses, co-working space cost comparisons, and detailed documentation of the work I was able to complete from the hotel room. Must have been compelling; Finance approved the reimbursement.

But I didn’t feel great about eating the credit card interest incurred while waiting for reimbursement, which Finance didn’t want to cover. Out came ChatGPT to draft another exhaustive (exhausting?) argument, including opportunity cost analyses. 2 for 2, I got the interest charges reimbursed too.

Now? I book everything through the travel agency’s platform, no matter how absurdly overpriced it is. All because they refused my entire reimbursement request over the $20 late check-out fee.

14. The twist

In my first role ever managing people, I was a student “account executive” at the on-campus design shop that made posters for the on-campus clubs and activities. One of the designers I managed worked a completely different schedule than I did, due to class hours. He was consistently late on his projects and deliverables. So I asked him to start giving me a rundown of the projects he worked on during his shifts. I explained it just as a “I worked on projects X, Y, and Z. I’m almost done with X and Y, Z will be a little longer because of Reason. I will connect with client for project K on Tuesday.” Really brief and standard status updates.

He responded with malicious compliance and gave me essentially a minute by minute reporting of what he did during his shift. Obviously trying to overwhelm me with detail so I’d stop asking.

I responded – yes perfect. More of that. And just made him give me that level of detail for a week. I did finally catch him and tell him to knock it off and give me the correct level of detail. But I let him make himself miserable with his own “malicious compliance” for a week first.