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https://www.askamanager.org/2025/11/the-chili-cook-off-vote-buying-the-boudoir-photos-and-other-tales-of-holidays-at-work.html

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As we head into the holidays, we must solemnly reflect back on the stories shared here over the years about holidays at work. Here are some of my favorites.

1. The chili cook-off

I worked for a nonprofit, and every year there was a few months long period where every department would do some kind of fundraiser for the nonprofit. My department was famous for a lunchtime chili cook-off that included, of course, voting for a winner. It was my first year there, and my boss kept talking about how popular the chili cook-off was. We were advised we needed to quadruple our normal recipe to have enough for everyone.

One coworker launched in right away with BIG talk about her recipe. And the day of the cook-off, she kept going around and checking out the competition and making allusions to her to secret ingredients. When the judging was over, we learned that she won and she was ecstatic … but then it came out that she’d been buying votes all afternoon! When the accusations were revealed, she refused to give up the trophy.

Oh, and remember the quadruple recipes. Turns out that was bananas, and since everybody ate only a couple spoonfuls of each chili, there was an exorbitant amount left over. Another coworker carried her crockpot of leftovers back to her car and spilled that triple recipe of chili all over it. (2024)

2. The bites

During a potluck, someone (the office never discovered who!) went to the meeting room where the potluck had to be held and took a single bite out of every biteable thing. Scones, bread, fruits, pizza slices. Just one single bite. (2024)

3. The bourbon balls

Many years ago, I worked at the corporate office of a regional retailer. I worked closely with the senior VP, and while he could be a pill at times, I genuinely liked the guy.

One year, I found a recipe for bourbon balls that I decided to make up for the holidays. Knowing that the SVP had a giant sweet tooth and also that he was very fond of bourbon, I brought him a container of several dozen bourbon balls, thinking (foolishly) that he’d enjoy them over the course of several days.

He did not spread them out over several days. He chomped through the entire container in a single afternoon, ingesting a significant amount of bourbon and a whole lot of chocolate in the process.

As it happened, that day turned out to be the day the boss was going through the list of employees to decide how much each of us would get for a year-end bonus. And everyone was quite astounded that year at his unaccustomed generosity in deciding the bonus amounts.

For some reason, every year after that, multiple co-workers would pull me aside in early December to urge me to make up another batch of bourbon balls for the SVP the week before Christmas. (2022)

4. The photos

My dad was a firefighter. They throw wild parties. Not officially Fire Department parties, they just happen to have a raging house party that could rival any fraternity, and invite everyone from work. The story I was told is that at one of these parties, Fireman Bob — who was in a prank war with Fireman Steve — snuck off to Steve’s bedroom and took “boudoir” photos on his bed. He yanked his tighty-whities up between his cheeks and took about a dozen Polaroid photos, leaving them fanned out on Steve’s dresser. Steve said nothing the next shift. Steve never did say anything. He didn’t have to. The next year, Steve gave everyone in the department a photo calendar, featuring Bob’s fancy pictures. (2024)

5. The pizza oven

At my last job, I invited a bunch of coworkers over for pizza from my wood-fired oven. It’s a serious piece of kit – it’s effortless to crank it up to 900 degrees, and it’ll put out a Neapolitan pizza in about a minute and a half. My coworkers brought a ton of beer, and I slung pie for hours while we all debated the merits of various IPAs. While drinking them.

When everyone’s pizza urges were sated, I closed the oven door and let it start to burn itself out, which takes over a day. My wife and I know to never open the door once it’s time to let the oven wind down, but my coworker Bill didn’t know the rules. And Bill was very deep in his cups. So he bellowed, ‘Man, I wonder if it’s still hot in there?’ and grabbed the door.

One of the interesting side-effects of flameless combustion in a low-oxygen environment is the buildup of pyrolytic gases in the oven. This is more than an academic point. PROTIP: when your drunkass opens the oven while your host screams NOOOOOOOOOO and tackles you, the inrushing draft of oxygen will result in explosively energetic resumption of combustion, firing a jet of howling flame across the patio and lighting several pots of decorative plants on fire. And that’s if you’re lucky enough to be Bill, and aren’t just lit on fire like a human road flare. Maybe just don’t. (2017)

6. Crockpot discrimination

Years ago the floor manager banned crockpots from the work floor where teams would use an empty cubicle for team birthdays and celebrations due to ongoing issues. Fast forward a few months; a team brings in a crockpot for an event. An outraged employee approached me yelling that it wasn’t fair the other team could have crockpots and hers couldn’t. She looked me in the eye and completely seriously told me, ‘This is crockpot discrimination!” (2022)

7. The statue

I was invited to my boss’s house for an employee holiday party. This small business was owned by a married couple who were also landlords, so they were pretty wealthy and had a huge house. I was walking around admiring their art when I came across a statue.

A nude statue.

A nude statue of my boss. (2021) 

8. The safety’s committee’s mugs

Our safety initiative committee gave us beautiful logo’d mugs, lovely huge ones – that had a shiny gold enamel on the outside. They were neither dishwasher nor microwave safe. About an hour later, they came and took them all back after someone microwaved one and caused major, massive sparking, panicking half a lunch room.  (2022)

9. The first job

Many, many years ago, at the start of a new job, I was put in charge of the holiday party for over 200 people. I was young and this was my first professional job in my chosen career field. My boss left on maternity leave with little direction. I got the caterer who did my wedding. My assistant was a party planning expert and she handled decorations, etc. based on previous parties.

It was a fiasco. We ran out of food in about 45 minutes. Before she left, the boss got karaoke for the entertainment and nobody wanted to sing in front of basically a group of strangers with some coworkers thrown in. It was open bar, so everyone sat around and drank … and drank. We had one of our maintenance guys dressed as Santa with a sleigh and artificial snow. He drank too. The end result was not pretty. The next day, Santa had to be bailed out of jail for DUI, the rented Santa suit was a total loss, and the local leadership was scrambling to hide the entire fiasco from our corporate HQ. Yeah, the party the next year was quite different. I was still in charge, we still had liquor, but I learned so much. (2022)

10. The surprise

In a previous life/career, I worked in a regional office in Texas supporting salespeople in seven southern/southwestern states. One year, our region had an in-person sales meeting that coincided with the holiday season, so our manager thought it would be a good idea for the salespeople (all from out of town/state) to mix and mingle with our office staff socially at a well-known Texas chain restaurant. Plus-ones were encouraged for our office staff, though of course our sales folks did not have their spouses or SOs with them. Of the five office staff, three of us brought our known significant others, one person came solo, and our office assistant, T., who I loved dearly and who was also a little rough around the edges, brought a person none of us had ever met and who looked like he had literally time traveled in from Lonesome Dove or was the long-lost brother of Sam Elliott, complete with cowboy hat and duster coat. He spoke zero words to anyone. An hour or two into the event, I found myself sitting with my spouse and a couple of our sales folks, all of us a few beverages in, and someone finally asked, ‘So, T, who’s this?’ because it was getting awkward that this one individual was such a mystery to us all, and there were only about 20 people there total!

T calmly replied, “Oh him? He’s my f–kbuddy.”

My spouse and I still quote this memorable gem of an introduction. (2023)

11. The poop

Someone pooped in an attorney’s trash can one year during the office party. (2017)

12. The artificial trees

Our admin was retiring. The admin had a habit of claiming things or just straight up taking them, and treating coworkers like trash. As a result, the admin was not very popular.

Before they left, they announced that two dusty old artificial trees in the lobby belonged to them, and they would be taking them. Cue the consternation of the entire office, who apparently couldn’t function without the trees. After ignoring all the bickering and wailing, the admin loaded up the trees and drove them a quarter mile to a thrift store and donated them.

End of story right?

Except the very same trees made a surprise appearance at the holiday white elephant a month later. Cue cheers and cut throat fights to win them. The eventual winner bequeathed the trees to the office in perpetuity.

Turns out a coworker called the thrift store, claimed a confused relative donated the trees, and begged for their return. They then hid the trees until their triumphant reveal at the party.

The office continues to reference the reinstated dusty old artificial trees and the story of their rescue with great fondness. (2025)

13. The hometown hero

This is actually a heartwarming story that despite being more than 15 years ago still makes me really happy.

So mid-2000s. I worked at a pediatric hospital. Anyone who is in-patient on Christmas day is SICK. There are no scheduled surgeries, everyone who can be safely discharged for a day generally is. It is rough for families who observe.

This is when American Idol was THE thing. And a contestant from our city had done well the prior season — hadn’t won, but kind of ‘hometown hero.’ I didn’t watch the show so wasn’t super familiar, but I’d heard about him. We heard he was visiting with his family. Figured that they’d stop in a couple rooms, get some photos/PR, and go on home.

Readers, I kid you not, this man, his brother, and their parents visited every single child in the hospital. They were there for hours and hours. They put on gowns, masks, and gloves and took them off again. They held babies. They sang carols with families and staff. The singer guy was, uhh, surprisingly handsome in person. He made the adults and teenagers blush with his charm – including me.

I’ve never seen anything like it, before or since. It must have been so exhausting for him and his family — both physically hard, rough on their voices (so much singing!), and emotionally fraught — so much heartache and sadness. But the joy they brought to everyone, including this pessimistic Jewish woman who always works on Christmas cause it isn’t my holiday … well, it was certainly my most memorable Christmas. (2022)

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https://www.askamanager.org/2025/11/how-do-i-tell-my-coworkers-im-getting-a-divorce.html

https://www.askamanager.org/?p=34611

A reader writes:

My husband and I are splitting up after eight years together. We’ve had issues that we’ve been working on for a long time, but the final split happened fairly suddenly and I’m reeling right now.

On top of everything else I’m dealing with now (including finding a new place to live, getting off his health insurance, etc.), I’m wondering how to talk about this at work. My coworkers have met my husband at many events over the years, and I’ve talked about him a lot at work. I don’t know how to tell people we’re splitting up without inviting a ton of questions, none of which I’m really ready to talk about right now, and I also don’t want to trauma-dump on people I work with!

We do usually make time at the beginning of our team meetings for people to share any personal updates so I thought maybe I could mention it then, but people usually share happier things like an upcoming vacation or (sob) a wedding. Do I just … announce it then and say I don’t really want to talk about it? That feels incredibly awkward. But telling people one-on-one feels awkward too, and that would be a dozen individual awkward conversations instead of just one big one.

I’m also undecided on whether I’m going to change my name back to my maiden name, but if I do that, I’ll obviously need a way to explain it.

I also will need some time off to deal with logistical stuff, like lawyers and my impending move. My boss is pretty flexible with time off, but I’m worried this is going to take over my life for a while. Can I just … say that? Like explain that I’m about to have a couple of months of a higher-than-normal level of outside commitments, but that it won’t go on forever?

An additional complicating factor is that our professional worlds have some overlap: we’re in adjacent industries, and we know a lot of the same people professionally. I feel like I’m going to be fielding “how’s Jim?” inquiries for years and having to re-explain the divorce every time.

You can read my answer to this letter at New York Magazine today. Head over there to read it.

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Posted by Ask a Manager

https://www.askamanager.org/2025/11/how-do-i-deal-with-badly-timed-questions-as-a-manager.html

https://www.askamanager.org/?p=34577

A reader writes:

I’m student work head at a university library — basically, I’m a student managing the regular student workers as a way of getting experience in management, leadership, etc. One of the workers has a bad habit of asking questions about everything. Usually it isn’t too bad, and of course curiosity should usually be encouraged, though it can derail conversations.

But recently, there was an incident where some of our just-put-up Christmas decorations were stolen. Naturally, I was upset, and I happened to mutter, “Whoever did this is a real berk.” (I don’t know why I chose that word — it was just the first that leapt to mind.) Overhearing this, she asked, “What does that mean? What did you say? Is it like the f-word?” (The last was in response to my attempt to answer by saying simply that it was a rude British word.)

She would not stop asking about it, and given that I was already in a bad mood from the stolen decorations, I started getting upset. I managed to get away before blowing my lid, but I am utterly perplexed that, seeing that I was upset, she decided it was time to begin an interrogation.

How should I (a) apologize for any offense I gave in my hasty departure, and (b) explain to her that there are times (such as when somebody’s upset) when it’s not appropriate to badger them with questions?

Was your quick departure actually rude? Because unless you were outright rude to her, this doesn’t sound like something you need to go back and apologize for. If I’m wrong and it was ruder than it sounds, then just be straightforward: “I’m sorry that I was short with you the other day after the decorations were stolen. I was caught up in addressing what had happened, and I wasn’t in a place to answer language questions, but I should have been clearer about that.”

For your second question, I wouldn’t go back now and chastise her about what she did; it doesn’t sound that egregious, more like she just misread what was happening on your end of the conversation. But since it’s part of a larger pattern of her derailing conversations, you can resolve to address that the next time there’s a natural opportunity for it.  For example, the next time she’s intensely questioning something in a way that’s disruptive, you can say, “I need to focus on figuring out X right now, so can you hold those questions for now?” or “Right now we need to get through topics X and Y, so I don’t want us to get sidetracked on Z” or so forth.

In other words, think about what you can do on your end to manage these conversations more assertively. In fact, I think the “berk” situation would have been a lot less frustrating for you if you’d done that! You probably would have come away less irritated if early on in that conversation you’d said something like, “Sorry, I’m right in the middle of dealing with this theft and I need to focus on that — give me some time to take care of this.” I think the fact that you’re not managing these conversations in the moment is making it more aggravating.

If addressing it case-by-case in the moment doesn’t solve it, then you can have a larger-picture conversation with her explaining that while you’re happy to answer questions in general, you won’t always be able to pivot to answering them right in the moment if something more pressing needs to be taken care of first. But that’s very much about the bigger pattern and not about the “berk” interrogation.

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