Wild Goose Chase

"He wanted a pomegranate for lunch and they were out of season, but that didn't stop him from sending me on a quest to every grocery store in town in search of a pomegranate."

"Multiple produce guys laughed at me, but that was the easiest $13/hr I've ever made."

-- LemonsofLifee

Hard at Work

"I had a boss once who spent all morning locked in his office. He asked me to come in after lunch where he showed me a handmade graph."

"He then proceeded to explain that this was a chart of all the sex he had ever had in his life."

" 'See, here it is blank until I joined the army. Then I went to a sex worker here. That's where you see the big jump. I was on two tours but then got shot in the face. I came back home and you see how it just drops to almost nothing.' "

"I was astounded."

-- Bolaixgirl_105

The Horror

"I had a boss sneak up behind a middle-aged female employee and pick her up, then immediately drop her down saying 'I didn't think you weighed that much!' He could not stop laughing."

"He was the principal. This occurred during passing period in a crowded middle school hallway."

-- jezebellrae

Wear's His Insecurities on His Sleeve

"I had a redhead boss who made us all sit down and watch a training video about how we shouldn't refer to him as a 'ginger' because it is bullying."

"No one had ever called him that."

-- RespectFar

Checks All the Boxes

"Organized a thoroughly awkward award ceremony once (that we never did again)."

"Asked a Mexican employee if his new baby's name was going to be "No Mas" during the shower we threw for him."

"Heard me once use the phrase 'economy of scale,' then used it wrong 5 minutes later in a conversation with different people."

"Didn't know the meaning behind 'Black Friday' and what it meant for a company to be 'in the black.' "

"Just like Michael Scott, only more of a di**."

-- mackenziefox55

You Just Can't Say That

"Never have worked for one myself, but my dad told me a story about his boss who was giving out awards to everyone in honor of how long they've worked there, and he would give speeches for each person."

"A woman employee received her award and he gave a speech about the story of how she came to work there. And he said, 'At first I didn't want to hire her because she was so hot.' "

"My dad's not working there anymore, but I love that story because I will never not picture Michael Scott giving Pam a Dundie and saying that about her."

-- Bananabreadandchill

Bigger Fish to Fry

"I literally had a boss who would stop us in the middle of our work and hold company-wide meetings talking about 9/11 truther conspiracies and chem trails. Mind you we were furniture-making company."

"He would get so caught up in his conspiracy theories that he forgot to order wood to make furniture one month."

-- PAzoo42

A Very Important Side Project

"I worked for a woman as her 'personal assistant/ cat sitter.' She was super rich and off the deep end nuts."

She had me order a mannequin online, and then paid me to take one of the mannequin legs to Nordstrom to try and see what suitcase I could buy that would fit the dismembered mannequin body, because she wanted to fly with the mannequin to Pittsburgh to display 'as her daughter,' dressed in her daughter's clothes, at that daughter's graduation celebration. buying the mannequin was a whole thing too."

"She kept trying to get me to order from "adult doll" websites because she didn't get it. lmao."

-- represent_represent

Company Incentives

"My boss used to carry around a backpack full of hammers and if you fell sleep at your desk he started banging a hammer on your desk until you woke up and then he would autograph the hammer and give it to you as a gift."

-- supersecretsecretary

Anything But Work

"We had kidnapping drills one day, where we learned how to 'not be kidnapped'. Notably, this was a regular, boring office in a regular, boring suburb. No reason why kidnapping would be on anybody's radar..."

"He and several of the guys randomly broke out into a push-up contest. Again. White collar office. Middle-aged dudes in khakis."

"Couldn't remember the nationality of our Hispanic colleague. Tried to 'learn Spanish' to make her feel special when she returned from maternity leave. (1) What he learned was NOT Spanish, and (2) she was from Portugal. She knew like, five words of Spanish."

"Disappeared for four days. No call. No email. Wouldn't respond to any of our attempts to reach him. Finally, someone drove out to his house to make sure he was alive. He was. He'd just forgotten to tell us he was taking the week off, and then lost his phone in a lake."

"There were many, many moments like these. Great boss. Genuinely cared about everyone in the company. Occasional moments of brilliance, where he really got things done. But OMG, so many moments of ridiculousness."

-- homeschoolpromqueen

The Great Golden Hamster Ball

"My boss is certainly Michael Scott-esque. When I first started I was essentially Pam as well since I was both receptionist and his assistant to some extent."

"My favorite story was back when we were prepping for a conference. Some context, he's terrible with the English language in general and will mangle phrases and descriptions to no end (how the turn tables...)."

"So on a group call he kept talking about wanting a 'golden hamster ball' to do giveaways with. Was raving about how great it would be spinning around while people walked by, all the while everyone on the call was just sitting in confused silence."

"However by that point, I had become so good at decoding his nonsense that I knew he was referring to a gold raffle cage and sent him image privately asking if it's what he was thinking."

"To this day he still talks about the fact I can read his mind and must be psychic. And he still refers to it as a hamster ball."

"All in all he's a pretty nice guy and a solid boss. Hired me based on a gut feeling and has been decent to me ever since."

"I think I knew it would be a good fit when during the interview he tried to tell me about the four pillars of the company and forgot one. Told me later it was Knowledge."

-- outofprintluv

"I used Michael Scott as a reference point for an old boss of mine from the moment I started working there.

"He made Chewbacca noises on the regular because one of my coworkers' names sort of vaguely sounded like Chewbacca (it didn't), used voice to text extremely loudly in his office for no reason to send really personal messages..."

"...got really excited and wore a specific vest any time we had after-work outings scheduled, shouted the same like 7 references to old movies and extremely awkward hip-hop song quotes 100 times a day..."

"...and insisted on greeting all our international coworkers very loudly in their language (they all speak perfect English, of course), looking around for approval afterward, and then fully giggling at everyone's French accents on conference calls. He also told me a lot about an improv show he did for a full year after it happened."

Just a Complete Human, Flaws and All

"That said - he had all the good parts too."

"He never hesitated go to the mat for any of us whether we deserved it or not, he gave really sage business advice and great examples of how to face challenges out of absolutely nowhere, and he came to every community play I did in the 4 years I worked for him - and told everyone else in the office how good I was in it for the following month and chastised them for not coming."

"When things really got serious or bad in my life, he couldn't have been more kind, helpful, and supportive."

"Honestly? Probably the best boss I'll ever have."

-- happydactyl31

Like a Spelling Test

"I had a boss that used to watch me through a gap in the glass partition between our desks. She wanted to see if I was paying attention during meetings."

"One day, I put a large folder to cover the gap and she freaked. I still laugh when I think about it."

-- harperv215

Questionable Hiring Practices

"Never have worked for one myself, but my dad told me a story about his boss who was giving out awards to everyone in honor of how long they've worked there, and he would give speeches for each person."

"A woman employee received her award and he gave a speech about the story of how she came to work there. And he said, 'At first I didn't want to hire her because she was so hot.' "

"My dad's not working there anymore, but I love that story because I will never not picture Michael Scott giving Pam a Dundie and saying that about her."

-- enlarged-tuna-fish