Our company finally managed to sign a contract with our clients in the middle of 2017. We ship and sell certain goods per KG to retailers via air freight in many different countries. We have one main client with whom we do most of our business, and we have a couple of shipments to them per week.

Every shipment involves a lot of documentation and there's a long procedure involving document creation and invoicing that needs to be followed to ensure everyone (the custom's broker, the client and the airport authorities) receives the documents they need. When we started exporting, the responsibility of organizing this mess fell to me and I was given a smelly heap of disorganized documents to streamline. Fortunately, over the months, I've managed to condense the procedure, and, with the help of a few well-automated Excel programs I wrote, the whole procedure gets itself done with a lot less work than before.

One quirk of this procedure is that all invoices need to be sent to a particular contact in our client's company. This particular contact somehow insists on using his private e-mail to receive work documents instead of his professional one, probably because he's able to work from outside of his office. I guess his upper management signed off on it since he never tried to be discreet. Usually, there would be no problem, except for the fact that this private e-mail has a limit of about 2MB per attachment received. If the e-mail has attachments that exceed this limit, the mail won't go through.

In the beginning we had big problems as I was attaching all 6 invoices into one mail, totaling about 5MB, and sending it to him and his coworkers. No matter how many coworkers I CC'd in the email, the one guy using his personal e-mail wouldn't get the documents and all hell would break loose every time.

Finally, to get around this, I started sending him 4 or 5 different e-mails, depending on the size of the shipment, as to break up the documents so he can read them. This worked fine for a while until one day my boss approached me and asked me about it. I confirmed to her that we were sending 5 different e-mails every time, otherwise our client wouldn't be receiving our invoices.

She was appalled, and started lecturing me about how "this wasn't good practice" and "to continue this way is not possible", and that I had to "find a solution". I informed her that if I join all the invoices together, the mail doesn't go through to my client's inbox, and if the client doesn't receive the invoices they can put in a claim through their system that eventually leads to us not being paid for what we exported. Still exasperated, she continues to sigh and keeps repeating "No, no, this is not how it's done, you cannot send 5 different e-mails to the client for his invoices!". Even though I try to explain it again to her, the lecturing continues regardless.

You want me to revert back to sending one e-mail, even though I know it will cause problems down the road when we stop getting paid? Alright, whatever floats your boat.

A day or so later, when we had our shipment, I sent one large e-mail with all the invoices bundled inside, which of course did not arrive to the client. I texted the guy responsible (the one using his personal e-mail) through messenger with some details about my Malicious Compliance, and much to my delight, a couple of minutes later he sends a LARGE e-mail, with our CEO and his CEO in CC, claiming that the documents were not received and this will result in us not being paid. I waited an hour or so and then sent him the 5 e-mails normally, with the invoices, as I always do.

The next day, my CEO calls me early in the morning to ask about the e-mail from the day prior. I explained to him that I was told to join all invoices into one email and that resulted in the client not receiving them. He, getting upset, tells me to "manage my own goddamn sector" and that I should do whatever it takes to make sure things run smoothly. I agree vigorously and grin, knowing what's coming next. Later on, my boss slinks into work, looking sullen, angry and depressed. She starts telling me how badly our CEO ripped into her for "something she didn't even know would be a problem" as I nodded solemnly.

Safe to say, she didn't interfere in the invoicing process for a while after that incident.