Funny Christmas Gifts for Your Boss (That Won't Backfire)

Do you actually have to buy your boss a Christmas gift?

No. Workplace etiquette runs downhill: bosses give to their teams, not the other way around, and a sensible manager won't hold it against you if you skip it. A few things worth knowing before you spend a cent:

• Check the handbook. Some companies cap or ban gifts to managers. Ask a coworker who's been there a while what happened last year.
• Group gifts are safer. Hive's etiquette guide suggests a team gift over an individual one, partly so nobody can accuse you of favoritism, and uses about $10 per person as a fair price in a group.
• Government workers have a hard limit. Under federal ethics rules (5 CFR 2635.304), a federal employee can give an official superior a non-cash gift worth $10 or less on an occasion when gifts are traditionally exchanged, and shared food in the office is fine. Passing the hat for a gift on an annual holiday is not. Agencies can be stricter, so ask your ethics office (here's the USDA's plain-English FAQ).
• Gifts don't buy raises. If you're hoping a mug will do the work of a performance case, it won't; our guide to asking for a raise has the emails that actually help. Brown-nosing also tends to get noticed by everyone except the boss, and the office politics survival guide explains how that plays out.

If you've decided to go ahead, because you like your boss or because the team is doing something and you'd rather not be the odd one out, read on.

How funny can you get? The 3-question joke test

Etiquette guides, including TechRepublic's holiday-gift rule book, say flatly not to give gag gifts at work. I half agree: a gag gift to the wrong boss is a career-limiting present. But plenty of bosses laugh at themselves, and for those, a joke gift is the nicest thing you can do. So test before you buy.

1. Does your boss joke about work, out loud, in front of people? The boss who says "per my last email" in a silly voice is a candidate. The boss who has never once smiled in a Monday meeting is a mug-and-pen boss.
2. Have you ever seen them laugh at themselves? Teasing is only safe with people who can take it. One self-deprecating remark in a staff meeting counts.
3. Would you be fine with the gift being read out at the holiday party? If you'd wince, don't buy it. Assume everyone will see it.

Three yeses: pick from the yellow list. One or two: stay on green. Zero: a nice pen and a card, and you're done.

One rule runs through all of it. Aim the joke at the situation (meetings, email, coffee, spreadsheets, Fridays) and not at a trait of the person. 'Meetings that should have been emails' is a joke everyone shares. 'You're a control freak' is a performance review.

25 funny Christmas gifts for your boss, sorted by risk

Green list: safe for almost any boss

Most are $10–25. If you only read one section, make it this one.

1. A mug with a meeting joke. "I survived another meeting that could've been an email" works on every floor of every building. Skip the ones that say "World's Okayest Boss"; that's yellow list material.
2. A desk plant in a pun pot. Succulents are the safe pick; a fake one is safer still for the boss who has killed two ferns this year.
3. A "meeting survival kit." A small box with good mints, a decent pen, a pack of sticky notes and one quality tea or coffee. Add a label. You've spent $20 and it looks like effort.
4. Meeting bingo cards. Print them yourself (free), fold in a card, and let the boss decide whether to play at the next all-hands. Squares like "circle back," "bandwidth" and "can everyone see my screen."
5. A good pen "for signing things." Wrap it with a note saying "for approving my time off." That's the joke, and the pen is actually nice.
6. A desk calendar with one joke a day. HR Approved Corporate Sarcasm is a 365-day office joke calendar, and a calendar is a gift they'll see every single day.
7. A funny book about work stress. HR Approved Corporate Therapy laughs at workplace stress and pretending to be fine, without picking on anyone in particular.
8. A book about the holiday party. Office Holiday Party Survival Guide is on theme and gives the boss something to flip through at the party itself.
9. Good snacks with a funny label. Fancy popcorn or chocolate-covered pretzels in a tin labeled "emergency meeting fuel." Food is the least risky gift on earth.
10. A "decision-maker" desk toy. A classic Magic 8 Ball sits well on a manager's desk: "Should we reorg? Ask again later."

Yellow list: only if you passed the joke test

The boss laughs at their own expense, and you've seen it happen.

11. A "Chaos Coordinator" mug. It's flattering and silly at once, and it suits a boss who runs a busy team.
12. A doorknob or desk sign. "In a meeting that could have been an email." Hang it on a door. They'll use it.
13. A tiny "Boss of the Year" trophy. Keep it small, cheap and obviously a joke. A giant one reads as sarcasm.
14. HR Approved Ways to Say Things I Can't Say Out Loud. For the boss who has said "interesting approach" with a perfectly straight face and meant something else.
15. HR Approved Ways to Say "Do Better" Without Drama. Aimed at managers who dread review season. Only give it to someone who has complained about giving feedback; otherwise it looks like a hint.
16. Ways to Lead Without Losing Your Mind. Perfect for a boss who was promoted recently and is still working out who they are as a manager.
17. HR Approved Dad Jokes. If your boss already tells dad jokes at stand-up, you're giving them ammunition, and everyone on the team will benefit.
18. Office Survival Explained by Cats. For a boss who has a cat as their phone background. Also the gentlest book we publish, so good for borderline cases.
19. HR Approved Corporate Trivia. For a boss who organizes the team quiz night or loves a Friday game.
20. HR Approved Would You Rather. A good fit if your boss opens meetings with an icebreaker.

Group gifts: the team pools together

Everyone chips in $5–10 and nobody has to carry the awkwardness alone. Hive's guide recommends experiences like a restaurant gift certificate, a massage or a team-funded lunch.

21. A team lunch with the boss as guest of honor. They get a nice meal and you get a break from desk salads.
22. A big card with funny captions from each person. Pass it around, and ask everyone to write one short line. One of the best gifts a boss can get is evidence that people like working for them.
23. A "greatest hits" frame. The team's top five quotes from this year's meetings, framed. ("Let's take this offline." "I'll socialize it.") Bosses keep these for years.
24. A coffee or tea tasting basket. One basket, six flavors, a funny tag for each ("for Mondays," "for after the budget review").
25. A joke certificate. "This certifies that [Boss] has survived 214 meetings, 3,000 emails and one fire drill during a presentation." Print it, sign it, put it in a cheap frame.

Match the gift to the boss

What not to give your boss, even as a joke

• H2 {id: not-to-give}: "What not to give your boss, even as a joke"
• Alcohol, unless you know the policy and the person. Some people don't drink, and some offices ban it.
• Cash or an emailed gift card. Both feel impersonal, and cash looks like a bribe.
• Anything about their appearance, age or health. No "over the hill" cards, no diet jokes.
• Perfume, lotion or grooming products. Too personal; skip it.
• Self-help books. A gift that says "you need to improve" doesn't read as festive.
• "World's Worst Boss" anything. The joke is old, and if the boss has had a bad year it stings.
• Ways to Tell Co-Workers They're Stupid. We love this book. Do not wrap it for the person who signs your review.

What should you write in the card?

A card with a good line matters more than the gift. Use one of these, or steal the spirit:

• "Thank you for never scheduling a meeting at 4:55 on a Friday. We noticed."
• "Happy holidays. This mug is the only thing here that holds your coffee and doesn't need an agenda."
• "To the one person who reads the long emails. Merry Christmas."
• "No action required. Just enjoy."
• "From all of us, who will pretend this was your idea."
• "Thanks for the year. Please don't ask us to circle back to it."
• "Merry Christmas! This is not a hint about the budget."

If you want phrases that are polite on the surface and sharper underneath, there are plenty in our list of HR approved ways to say things at work.

What if your boss gives you a gift and you got nothing?

It happens. Say a warm 'thank you, this is so thoughtful,' and leave it there. Don't rush out and buy something in a panic; a gift bought in the next hour is obviously a reaction, and it makes things awkward for both of you. A handwritten thank-you note the next morning is plenty. If you want to return the gesture, a small shared treat for the whole team works.

And if you are the boss reading this: our post on funny employee appreciation gifts is written for your side of the desk, with ideas under $20.

What if you are buying for the whole office, not just the boss?

Then you're in gift-exchange territory, and the rules change a bit. Our funny coworker gifts guide is sorted by budget, and the Secret Santa guide for coworkers you don't know covers the draw-a-name-from-a-hat situation, including what to do if you pull your boss.

FAQ

Start here

If you're still not sure, begin with HR Approved Corporate Therapy for a boss who looks tired, or the Corporate Sarcasm desk calendar for one who laughs easily. Add a card from the list above and you're done. Then go home and enjoy being the employee who didn't overthink it.

Sources

• H2 {id: sources}: "Sources"
• Cornell Law School Legal Information Institute, 5 CFR 2635.304: Gifts to superiors
• U.S. Department of Agriculture Office of Ethics, Subpart C: Gifts between employees (FAQ)
• Hive, Should You Give Your Boss A Gift? Dos and Don'ts
• TechRepublic, The etiquette rule book on holiday gifts for your boss