What's something your boss did to embarrass them self?

So I worked as team leader of a high preforming group of marketing consultants a few years ago. Fairly young, self taught and motivated people with specialist knowledge about various fields of digital marketing in particular. Companies that weren't big enough to have their own inhouse digital competence would hire us. Right when Google Adwords, SEO, affiliate networks, remarketing/retargeting and all that jazz was new, this was big buisness.
We got a new CEO after the last one "took a break" due to some unforseen consequences of a spontaneous purchase of a rather private and carnal nature. New guy looked and behaved like That Guy from futurama. It looks fun on TV, in reality working with someone like that is cringey and awkward. Aaaand, much like That Guy he was more than a little out of touch with technology. Not quite "frozen for a thousand years" out of touch, but "Could you call goggle and ask about X" out of touch. Great thing when you're supposed to manage a company of IT/marketing consultants.

Anyway! He starts of by telling us in great and florid detail about himself, his many accomplishments and all the places he's seen and people he's met. You know what happens when you tell a large group of 20-30-somthing people grandpa stories? They pick up their phones. He gets to the part where he left his old superstar CEO job because he was bored with it. Sounded a little thin on the details. The deafening silence of 100 people simultaneously googling "That Guy leaves ThisCorp" could not be heard while he droned on. Well apparently he too took a break but after some questionable invoicing routines were discovered. To the tune of about $25M. Oh well. They say the best financial people always walk the razor's edge between getting caught and just almost getting caught, maybe this'll be good.

After the big introduction he wants to meet me and my team because we're the highest grossing team in the company. Fine. So we sit down in a conference room. Glances are exchanged. Eyebrows discretely raised. "I'm sure this will be a postive thing for us" I said, because that's what I'm supposed to say I guess.

He walks in the room, says hi and proceeds to spend 45 minutes absolutely fucking shitting on people born in the 80's. They're all lazy. Impossible to motivate. Entitled. Undisciplined. "Anyway, I'm so glad we have a more senior team like you guys to show the others what motivation and self discipline can achieve".

The tension in the room where everyone was born between 1981 and 1988 was pretty god damned thick. I think he could sense that something maybe wasn't going quite as he expected but in true That Guy fashion he plowed on and proceded to spend another 15 minutes making sexist jokes about how parental leave should be left to women. Telling us that it is despicable for a man to take parental leave and finally finishes up by proudly annoncing that he has barely seen his kids grow up because he worked so much. That went over super well with my almost exclusively female team led by yours truly, returned from his parental leave a few weeks before.

After the meeting I asked everyone to stay a while and basically had to promise that I would stand between them and him in all things or they'd all walk out the door. Keep in mind, these were high preforming consultants with a very rare combination of technical know-how, interpersonal skills and, full disclosure, good looks (yours truly not included). "Walking out" is not an empty threat. There were a handful of other companies doing what we did, either one would gladly have offered either one of us a desk the same day and having someone walk out usually also meant losing a fair few big accounts too.

Having finally calmed things down a bit I go on a business trip the next day. Short plane hop an hour away to meet a big client. I step out of the meeting, turn my phone on. From [my most senior employee] "Call me".

While I was in a meeting our new CEO decided to fire my most recent hire, a brilliant social media consultant who was something so rare as a social media manager who actually had concrete ideas on how to drive business and not just a failed blogger looking for a paycheck. I spent months courting that girl before she finally signed on with us and she had brought companies who were in the "social media is for young hip companies, not us"-bracket into the fold. He fired her because he wanted to "streamline the organization" so he fired everyone hired in the last six months.

I lost my team that day. My team quit one by one over the course of a few short weeks and I did nothing to stop them. I quit soon after that, having made sure that all of our clients had smoothly transitioned to competitors or recruited competent people themselves. That Guy managed to drive a flourishing consultancy business into the ground in a year and into backrupcy in one more.

And here's the kicker. You'd think I'd be upset about this. I'm not. He didn't do anything wrong, not really. He did exactly what had worked for him over a long career as a manager. That Guy was just hopelessly out of touch with the business he was assinged to manage. Ok, he was a giant douche of course but his business strategy was sound. 30 years ago.

/r/AskReddit Thread