Another excellent Ask-Design-Mom question that I would love some help on:

Any ideas on what to get your boss for the holidays? It’s easy to find creative gifts for women, however, my boss is male and 50ish. Sincerely, Sharai

Yes indeed, Sharai. The employer gift is tricky. You can’t get anything too nice because then you’re too obviously brown-nosing. Plus, you’re getting paid less, and it would be weird if you gave your boss a more expensive gift than he/she gave you. Additionally, in many cases, the boss-employee relationship is pretty formal and you may not have any idea what the boss would like. And you definitely don’t want to give them something they dislike.

So here are a few ideas, and I’m certain my clever readers will add more:

A) Observe carefully your male-50ish-boss’s office and take your cues from what he already likes.
-Are there model cars? Add one to his collection.
-Sports paraphenelia — maybe from a specific team? Find some signed memoribilia on Ebay.
-Books from Oprah’s book club? Get him the latest in hardcover.
-Pictures of his kids/grandkids? Find a frame that would look good in his office.

B) If the boss isn’t giving any clues, try these very-neutral-but-nice ideas:
-Get a gift certificate for a good restaurant near your workplace — somewhere he could go for lunch.
-Get him the latest industry related book. If he’s in advertising, look up the most recent advertising best-seller on Amazon.
-Give a classic Holiday CD. Maybe Frank Sinatra singing the Holiday standards.
-Chocolates. Unusually good-looking ones. Even if he’s not a chocolate eater, it’s nice to have something to offer visitors.
-A (small) plant for his desk/shelves. If it’s not his thing, he can claim a brown thumb and let it die.

That’s a start. Dear Readers, please chime in and I’ll keep thinking as well. . .

Cactus exchange pic from Getty Images.