sure here's a comical one:
we were a healthcare company so HIPAA was very prevalent, and so that entailed a locked office which further included either taking your laptop home, or locking it up in a drawer. there were plenty of people who would just leave the laptop on their desks when leaving to go home due to the fact that the office was locked; one day I come into the office and am met with a bunch of coworkers telling me that the CTO came in early today and found that the door was open and all of the laptops people had left lying around were outside in the hallway, stacked. nothing was stolen, but clearly someone had broken in. it made zero sense, and a different coworker said that she felt unsafe and that we should call the police. the CTO immediately said that that was unnecessary and that we should just be more cautious. a few hours later we found out that this was all a ploy/lesson to teach us to lock our laptops away, and that the CTO was the one that stacked them up outside. he was later asking whether he should resign because of this embarrassment. real michael scott shit.
a non comical one:
we needed to build a viable infrastructure and one of our smart engineers found that we could use a hipaa compliant service (aptible) as a fast way, and spend a bit more. however the ancient dudes wanted us to hire some third party consultancy to build out some crazy complicated AWS stack, and unfortunately that was what we ended up doing because hierarchy. the project was being led by a person who wasnt an engineer, and surprise surprise, we were also locked into some crazy contract where regardless of the work they did, we still had to pay them an insane amount of money per month. the project dragged and dragged, and ultimately didnt work out. we had some half assed/half done AWS stack that no one knew how to deal with so NOW we had to hire an infrastructure dude to finish/manage it inhouse. so we hire this "hotshot" who turned out to be literally a money dump as well, and would show up to work about 45% of the time. no one knew what he did. it took him like 7 months to get that other project to SOMEWHAT work. he was getting paid i think like 200k to sit around and really do absolutely nothing. i was also convinced he was addicted to drugs on the side based on his manners when he actually managed to show up to work. by the time i had left, that AWS project was still incomplete and im positive that anyone with half a brain/aws experience could have built that stack in a month and a half.
and then of course there was the day to day of trying to get information from the acquiring company's employees and trying to cut the red tape of actually getting shit done, but they were very clearly used to bureaucracy type of work environment where every decision took ages, and some people were offended by the most minor things when we attempted to speed things along.