In a meeting the vice president of IT asked me “How long would it take you to re-write our CRM in XML?”
I responded “I’ll have it done by the end of the day if you can tell me what XML stands for.”
VP walked out of the meeting not saying a word.

Worked with a European consulting company to integrate some shared business data (aka. calling a service).
VP of IT called an emergency meeting (IT managers, network admins) deeply concerned about the performance of the international web site since adding our services.
VP: “The partner’s site is much slower than ours. Only common piece that could cause that is your service.”
Me: “Um, their site is vastly different than ours. I don’t think we can compare their performance to ours.”
VP: “Performance is #1! I need your service fixed ASAP!”
Me: “OK, but what exactly is slow? How did you measure their site? The servers are in Germany”
VP: “I measured performance from my house last night.”
Me: “Did you use an application?”
VP: “<laughs> oh no, I was at home. When I opened the page, I counted one Mississippi, two Mississippi, three Mississippi, then the page displayed.”
Me: “Wow…um…OK…uh…how long does our page take to load?”
VP: “Two Mississippi’s”
Me: “Um…wow…OK…wow…uh, no, we don’t measure performance like that, but I’ll work with our partners and develop a performance benchmark to determine if the shared service is behaving differently.”
VP: “Whatever it is, the service is slow. Bill, what do you think is slowing down the service?”
NetworkAdmin-Bill: “The Atlantic Ocean?”
VP got up and left the meeting.

In a previous job as a system developer I had an office with a door. Unfortunately, the boss of the company had heard of "open door"-policies, and insisted on all physical doors being open all the time so he could pop his head in unannounced every 15 minutes with random chit chat and to see how work was going... :x

In order to reduce support costs, manager instructed his team to remove all logging/reporting of errors in the company’s CRM application.
Team’s support tickets went down 80%, manager received an award for his efforts, but mysteriously, DBA/support workload increased, bad/missing data,
increased support tickets in other areas of the business (shipping, etc. that relied on correct data from the CRM) and other side-affectual behavior.
Even after pointing this out this correlation, showing before/after code, no one believed the two were related and I was accused of not being a ‘team player’.
“You and the other teams need to learn from his example!”. As ‘punishment’ was I was moved to the team managing the CRM application.

Worst documentation I've seen?

Our "Coding Standards" 20+ page document. The team who put it together got so detailed, there wasn't much 'wiggle room' for natural deviations in a developer's coding style. For example, a section devoted to no abbreviations. So if you had a variable 'invoiceId', they complained you violated 'standards', even though 'invoiceId' matched a field name in a database table. Using Dapper or another ORM that relied on the 1:1 name match? Nope, you were still forced to inject your own mappers so the code didn't violate standards.

As you can probably guess, such a long, detailed document would have contradictions. I pointed out one of the contradictions. Example:

Page 5: Section B, sub-section B-5, paragraph 3 : "To minimize network traffic, when querying the database, request all the data necessary for the application."
Page 8: Section K, sub-section K-2, paragraph 4 : "For maximum performance, when querying the database, request only the most minimum amount of data necessary for the application ."

In a review I pointed out this contradiction (there were several more)
Me: "If we satisfy A, one could say the code is in violation of B. Which is it?"
<Pointy-Hair-Boss throws his pencil on the table>
PHB: "WHAT IS YOUR PROBLEM WITH STANDARDS! It couldn't be more clear! We are a company of standards because without standards <blah blah..straw man argument..blah blah>"
<deciding not to die on that hill, I move on>
Me: "On page 12, paragraph 9 code is in violation if a method has more than 3 parameters. That seems a little restrictive given our interaction with 3rd party products."
PHB: "There you go again. As stated in the document, ALL code used by the company will comply to our standards. What part of 'ALL' do you not understand?"

Was he bluffing about requiring 3rd party vendors complying with our standards? Heck no. That's a story for another day.

Prior to a tech conference in Las Vegas, the department manager held pre-meetings (yes, more than one)
with the developers to outline their expected behavior (yes, there was an outline in Word). Since
they would be representing the company, professionalism would be expected at all times, not just
during the conference. He knew he couldn’t forbid gambling and drinking, but any unruly behavior
that could reflect badly on the company would be dealt with severe disciplinary action up to and
including termination. He wrote up very detailed itinerary, what track each developer was
expected to attend, meal times (yes, what time to get up for breakfast, meet for lunch, and time
to eat at night). First day was fine, casinos are kinda crazy so having an itinerary wasn’t the
worst idea and no one got lost. Days following however, got interesting. After the first evening
meal, everyone hit the casino as expected (too much drinking, etc..normal single twenty-something
guys do) and the manager especially had a good time.
Next, and following days, the manager could not be found in any of the ‘required’ technical tracks.
Not that they cared that much, but couple of devs decided to check out the casino, and sure enough,
there he was at one of the tables, drunk, and being very loud around at 10 in the morning.
Again, nobody cared much, manager wasn’t very tech savy, and so attending a track on C #threading
would be lost on him. It was more of ‘do as I say, not as I do’ kind of thing.
The manager kept to the itinerary, he met everyone at breakfast, lunch, and dinner, etc, but the
‘WTF’s didn’t get good until the manager was bragging about how wonderful the conference was, how
much he was learning and couldn’t wait to get back and start implementing everything he was learning.
It was such a joke, the guys would bait him on tracks they know he didn’t attend and an amazing amount
of BS could not be believed.
On the last day of the conference several decided to follow him after breakfast to see where he went
and watched him go into a technical track, just to walk back out and straight to the casino floor.
Again, around 10, he was drunk, not quite as loud until he threw up in a trash can (they said it was quite a scene).
He left to go back his room, which they suspected he took a nap before meeting everyone for lunch.
After that, they gathered his daily itinerary was:
- Get up for breakfast
- walk around and make sure it looked like he was heading to a track
- head to the casino
- take a nap
- eat lunch
- walk around some more
- head to the casino
- take a nap
- eat dinner
- head to the casino
- wash-rinse-repeat
Last day caught up with him. After about week of drinking, staying up late, etc, his body (he’s in his mid 50’s, 350lbs+, so imagine)
kinda’ gave up. Could barely walk 50 feet without needing to sit down, and the flight back was worse for everyone,
throwing up occasionally, moaning, you get the idea.
On the following Monday with the VP if IT, everyone was discussing the conference, what they learned,
what they liked, etc, the manager also bragged, yes bragged, on how tired he was because of how much
he learned and the reason why he probably caught the flu (he couldn’t hide how sick he was on the flight)
saying “When you’re in the learning zone, you lose track of time and then you are so exhausted, your
immune system is susceptible to all kinds of things.” . VP was so impressed by his dedication and
fighting through the exhaustion for the good of the company, he gave him the rest of the day off.
Other devs? No, they had to go back to work.

At a previous job, boss & owner of company would waste hours of my time to show me, at his own desk, every small detail of some random feature he had fallen in love with on some random webpage he found, while saying "I don't want to disrupt your plans or anything, this is just something to keep in the back of your minds, as this would be a really nice thing to have, even tho none of the clients have asked for this and I have asked no one else for a second opinion, and I will most likely ask you to remove this feature in the future because I will finally have realized it wasn't that good an idea anyway."

Ok dipshit, what the fuck are we supposed to do with this information? Every week from this moment on you will ask whether we have found the time to implement this feature, even though you are fully aware that our schedule has no room for random, unplanned features and that we are already not able to meet the unreasonable deadline you pulled out of your ass two weeks into a development process that would end up taking 8+ months.

We are already overworked, we already work hours upon hours of unpaid overtime, and yet you still think it reasonable to pull us away from our work every other fucking day to talk about random extra features you want added, but don't want added to the roadmap because you want no delays... Fuck you, fuck your toxic attitude, fuck your meetings where you spend half an hour complaining about features we are still in the process of developing the backend functionality for (on test servers) not having the right font colour for the text, and fuck your legacy desktop software originally written in COBOL that you now want moved to "the cloud".

I would rather be unemployed and live as a hobo on the streets with a "will code for food" sign than work for you ever again.

Management directed a 2-month project including 5 developers, 3 DBAs, plus Q&A to replace a SOAP service that retrieved data from a single table. End result, project lasted 9+ months, 5 spectacular failed 3:00AM deployments, and a WCF service that retrieved data from a single table. Justification? Management wanted to eliminate SOAP, because SOAP uses XML and XML is slow. Thank goodness no one opened up Fiddler to see how WCF communicates.

Management forbade the use of XML in favor of the faster, formatted strings that looked like opening alligator jaws facing left and right. Yes, he used the term ‘alligator jaws’.