Bob Goldman
I don’t want to be judgy, but isn’t it getting a little late for you to decide on a holiday present for your boss?
You don't give your boss a present? You only think about what the boss gave you? That’s a mistake. Miss the holiday gifting season and your problem could be deciding on a gift for that friendly clerk at the unemployment office.
It’s not a surprise that many people forget to extend their gift giving upward. We tend to gift down, honoring those who work very hard and don’t get paid very much, which in no way describes your boss. There is also the Santa Claus Syndrome that affects many of us in the lower regions of the org chart. We believe that if we’re very productive girls and boys, a jolly C-suiter will visit our cubicles in the dark of night and leave us presents — like stock grants, and out-of-guidelines raises and maybe, if we’re lucky, a honey-baked ham.
Perhaps it is not in the true holiday spirit, but the fact that so many of your workplace besties will be thinking about what they will get, instead of what they will give, could be an advantage for you. Imagine how high you will stand in your boss’s estimation when you leave an unexpected gift in their inbox.
Yes, it could be a honey-baked ham, which would require a rather large inbox, but I actually think you could do better. Let’s noodle this together and see what we can come up with.
No. 1: Make it a passive-aggressive holiday.
Hate your boss, but feel you still have to give a gift? A personalized coffee mug is always a welcome addition to office life. Choose carefully and the mug you give will leave your boss uncertain over whether you are honoring them or making fun of them.
I refer to mugs with cheeky sayings, like “It’s Not My Fault,” or “Doing the Best I Can” or “Don’t Blame Me. I Only Work Here.” These are gifts which can’t be faulted, yet subtly — or not so subtly — undermine your boss’s totally undeserved belief in their abilities. (A colorful cartoon helps bring the message home. I recommend a fun photo of an ostrich with its head in the sand or a cartoon pirate walking the plank with hungry sharks swimming below.)
If some toady on the team has beaten you to the punch by giving your manager a “Best Boss Ever” mug, how about a book? The right title will show that you care and, at the same time, acknowledge that you know the boss is a big loser. For the milquetoast boss, my first choice is Predators in My Cuisinart, a cookbook popular among billionaire tech bros for its macho recipes, such as Tiger Steaks, Grizzly Burgers and Coyote Fritters, dishes designed to boost predatory behavior in the wimpy manager by eating what, given the opportunity, would happily eat you.
No. 2: Ozempic.
A gift of Ozempic isn’t cheap, but you could organize your co-workers to chip in. It’s a great way to demonstrate your leadership abilities and let your boss know that everyone has noticed they’ve put on weight and is talking about it behind their back.
No. 3: Don’t gag on gag gifts.
If your boss has a sense of humor, they will certainly enjoy a gift that brings holiday cheer to the entire office. A Whoopee Cushion is always great fun, especially when placed on the chair of your boss’s boss. Chattering false teeth will bring laughter and joy when placed on the conference room table right when your boss is about to speak.
No. 4: Ooh-la-la gift card.
Tie up the perfect gift. The right gift card could be a career-changer for you and a life-changer for your boss. Even $50 goes a long way when spent on S&M paraphernalia from Dungeon Master’s Toy Shoppe. Your gift will appeal to your boss’s punishing nature and give them something to fantasize about at work, allowing you to goof off.
No. 5: Merch.
Some of the least-liked holiday presents given to employees at holiday time are clothing items with the company’s logo on them. It’s different for bosses, who will be proud to display their loyalty to the company with a plush logo bathrobe with matching fuzzy logo bedroom slippers. What better way to say: You sleep all day, might as well be comfortable.
No. 6: The ultimate gift.
Make shopping easy by giving your boss what they want most — your resignation.
Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at bob@bgplanning.com.
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