10 Funniest Workplace Gift Debacles

We’re now officially in the holiday season — which in workplaces is also the season of workplace gift debacles! I recently asked readers to tell me about their most awkward workplace gift moments. Here are the 10 funniest and most awkward – from which we can draw the 10 key gift-giving lessons below.

1. Employees should not be pressured to send the CEO’s family on a ski trip

The second-in-command of my organization sent all of us this email: “Dear [staff], Each year we have done a holiday gift for [CEO] to recognize his leadership of [organization] during the year. Given the very busy holiday season, I’d like to start the ball rolling on the collection early this year in order to present him with his gift by December 18th at our annual retreat day. Please send your contribution to me and I will take care of purchase, etc. Last year we presented him with a two night stay at [resort] mountain for him and his family to go skiing and they loved it, so why not repeat the appreciated gift?”

Please note that the CEO is the highest paid person in the organization, and I am an hourly, part-time employee being paid less than the industry standard. I am incredulous at the expectation here. The wording of the email implies that the staff has no choice.

2. Not every sentiment needs to be shared

I did an 8-month internship, and my boss there was not the most pleasant of people. I would go weeks without seeing her because she was constantly calling in sick and she ignored me most of the time she was in the office. At Christmas, she popped her head in my cubicle long enough to say, “I was going to get you a gift, but I decided not to.” Thanks?…

3. No self-improvement gifts

I had a coworker who kept talking all over the office about how much she loved “The Biggest Loser” and Jillian Michaels, how she had friends who had tried the “30 Day Shred” DVD who had loved it and lost tons, etc. So her Secret Santa that year got her the DVD.

She opened it and cried, thinking she was being told she was fat. I really do think the giver had the best of intentions, but lesson learned. No diet/weight loss items as gifts, particularly to coworkers.

4. The boss’s spouse shouldn’t win the raffle

I worked for a small company, less than 20 people. It was privately owned by one person (Terry). Each employee’s name was placed into the hat for a prize ranging from $10 gift certificates to a brand new desktop computer and two tablets. Turned out the boss was included in the drawing. When Terry’s name was pulled for a prize, he politely declined it (as he should have, since his name should not have been included in the first place). But then, Terry’s spouse’s name was pulled for one of the MS Surface Tablets. And it was gleefully accepted by the spouse, who then drove away in a luxury car with the big door prize of the evening.


Problem? Spouse didn’t even work at the company. Spouse owned a company of their own. Spouse could easily have bought that tablet 100x over. Such a prize would have really meant something to the employees working there, some of whom were having a hard time making ends meet to begin with.

5. If you need a manual for gift exchanges, you’re doing it wrong

Several years ago, I took over a department that had been badly managed by a borderline psychotic micromanager. While trying to make sense of the ridiculous, overly complex procedures she left behind, one of my new employees gave me the “party procedures.” This three-page, single-spaced document detailed which holidays, birthdays, and anniversaries were to be celebrated and when, the types of gifts that were to be given to the various classes of employees for each occasion, and what type of food was to be served at each event. Even better, each employee was required to contribute money to cover cards and gifts. Aside from the fact that most of the employees were either part-time or not well-paid, requiring that employees contribute money to anything like that is illegal at our institution. I have no idea how my predecessor got away with it despite the fact that at least a couple of staff members over the years had quit over that very issue.

Needless to say, that was one of the first sets of procedures I axed, much to the relief of the staff. Now we have end-of-the-semester potlucks, and I buy the pizza. The one woman who was actually put out that people didn’t want to exchange gifts eventually got the hint and brings in cookies or candy as a gift for the entire department, which is fine but in no way required. So far, so good.

6. Keep it PG

We had a White Elephant gift exchange, and one of the gifts was a half-used jar of Vaseline and other sex accessories, including handcuffs. It was meant to be a joke, but came off entirely creepy because of the individual who gave it. He showed up halfway through the gift exchange, so we all knew which gift bag he’d brought. We had a great, easygoing office at the time, but reactions varied between stunned silence and awkward laughter. Even years later, no one really mentions that story, and that office doesn’t let you forget anything.

7. Not the place for pennies and paperclips

At one of my previous jobs, the organization did a gift swap each year. It was one of those ones where each person draws a number, which indicates what order you can choose a present and then people who come after can choose to either steal or take a new present.

The only “rule” was that the item you bought to contribute was supposed to be capped at $15. So the game starts and people begin unwrapping gifts and every item is relatively nice for being under $15 — gift cards to coffee and bakery chains, nice boxes of chocolate, etc.

We’re getting to the very end of the presents, and finally someone chooses this small-ish box. The person opens it and finds…a box filled with random junk — paperclips, pennies, screws, etc.

A kind of silence falls over the entire room for a minute or two, finally followed by some weak/nervous laughter. 

I don’t remember exactly how, but everyone knew who brought this box of junk. I’m not sure what the person was thinking — if he misunderstood and thought the gift swap was supposed to be like a White Elephant exchange or if he was just a jerk. (I do think he felt like a jerk after seeing everyone else’s gift.)

8. Be cautious when it comes to self-published poetry

One year I was stopped on the street outside work by a guy selling his self-published poetry book. It was full of pictures of sunsets and poems in the style of:
“I walk on the beach alone
The waves crash, 
But I feel at peace.”
Anyway, I declined to buy a copy and he asked how to find the office receptionist, so I directed him in thinking he’d be given short shrift there.

Fast forward to when we are all opening our work Christmas hampers and I discover that the receptionist was quite the poetry fan. He must have sold her a good 100 copies of his tedious book because every single employee got one.

9. No medical supplies

Once, during a Secret Santa, I got a (unused, thank god) plastic hospital bedpan.

10. Nothing from behind the couch, please

I think my worst gift exchange was the White Elephant when I worked at a rare books library, where everyone brought truly quirky awesome stuff to throw around … and what did I end up with? The library director brought a used cat toy that looked like a voodoo doll, complete with dust bunnies and cat fur still attached as if he’d just pulled from behind the couch. If you’re going to be “forgetful,” just don’t even participate!

Read on if you’re in need of some Holiday Gift Ideas for Your Employees, Boss and Clients.
You may also like this Forbes article, 10 Keys to Stress-Free Workplace Gift-Giving.













Alison Green

Alison Green writes the popular Ask a Manager blog where she dispenses advice on career, job search, and management issues. She's also the co-author of Managing to Change the World: The Nonprofit Manager's Guide to Getting Results and former chief of staff of a successful nonprofit organization, where she oversaw day-to-day staff management, hiring, firing, and employee development.

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  • Carly

    Great categories! I’m not sure where to place my own worst gift exchange though – it was less than a month after I’d started a new job, and all I was told is that we shouldn’t buy anything for the exchange; it was just whatever you had at home that you weren’t using. Most people brought in funny things, a couple people (including me) took it more seriously, and one guy brought in a *used cat litter pan*! He said he’d just emptied it out this morning, and hadn’t bothered to clean it out, since he was just going to throw it away otherwise. Ewwww! Really kind of destroyed the fun of it, and raised major red flags for me about the people I’d be working with going forward!

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  • http://abrightcontainer.tumblr.com/ manybellsdown

    I got a dead plant in a pot once in a White Elephant exchange. To be fair, I can kill any plant in a week so it was doomed anyway.

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