I've been lurking on the reddit sub for many years, but I finally have a story I'm excited to tell!
This is a story from a few years back, before the world went to shit.
I was working for a company that was mid-sized. We traveled a lot to meet clients, and had an expense policy. But because it wasn't a huge company, the expense policy was more of a guideline than a strict rule. Everyone knew each other, and we all acted sensibly.
I was supposed to attend a client meeting overseas in the UK. This was a somewhat last-minute request, and I had a personal vacation planned a few days after - also to Europe, but a different country. When I started looking up flights for the client meeting, I realised that instead of paying for my flight back home, it was cheaper for the company to just pay for a flight to bring me to my vacation destination. The catch was, I had an interval of 2 days between my vacation and the meeting - and I would need a hotel room paid for as well.
In the past, I would've just told my boss and he'd be ok with it. But the company had hired a HR director 2 months back. So I presented my plan to my HR director. I showed them the cost of flying me back home, compared with the cost of paying for 2 nights in a mid-level hotel while I worked remotely, and then flying me straight to my vacation. The latter would save them a fair bit of money - and as a bonus, I cut down on travel time.
The HR director didn't take kindly to my proposal, and accused me of trying to "game the system" to get 2 extra vacation days. He scolded me for taking advantage of the company, and told me to follow the expense policy "to the letter".
Did I mention that our expense policy wasn't very well written, and was more of a guideline than a strict rule? One example was the section on land transport. I can't remember the exact wording, but it said something like "we will cover the cost of flights to the nearest airport and subsequent car transport".
Most of us knew the spirit of the policy, and we'd fly in to a reasonably near airport and take a train or cab. Sometimes that meant flying in to a hub that was further. In this case, it would have been way cheaper to fly to London and take a train to the client's city for about $50. But hey, the HR director said to follow the policy "to the letter", didn't he?
I booked a flight to the nearest airport. It was literally twice the price of a flight to London - and we're talking thousands of dollars here. But hey, I'm just following the policy. Instead of taking a train to the city centre for $5 or less, I also took a cab, which turned out to be $40 or so. Gotta follow the policy, which doesn't cover trains!
When I came back from my vacation, I found out that my expenses had been flagged (no surprises there, it was way beyond what previous visits cost). I was called in to speak with the HR director about the issue. I simply pointed out to him that I had not been following the expense policy to the letter in the past, and I had learnt my lesson after the last time I spoke to him, so this time round I religiously followed the policy, and I would continue to do so in future.
HR had to spend a few weeks rewriting the policy. Because my expenses were out of the norm, the HR director had to get our CFO's approval to cover part of my expenses so they didn't have to explain it to the client. The CFO was pissed at the HR director for breaking something that had worked for years. I left after a year or so, but I heard the HR director was slowly pushed out and left a few months after me.