It's that time of year, so I asked readers about the best and worst business holiday gifts they've ever received. For now I'll focus on the bad business gifts--the horrifying mistakes that turned a holiday gesture of goodwill into a nightmare.

What surprised me most was the degree to which people remembered these gifts, in some cases decades after the fact. It's a stressful enough time without falling into these kinds of traps, so here are the top five things business people should avoid when giving gifts to employees, bosses, and colleagues.

Rule No. 1: Thou shall not be cheap. 

When David Viggiano worked as a television reporter in Chicago, "the holiday gifts got smaller and cheaper" each year, he recalls. "One year about a decade or so ago, we received a nail clipper. Yup, a nail clipper."

Adina Sweitzer worked for a company two decades ago whose owner's holiday gift to employees was a $10 voucher for concessions at a local sporting event. He'd only be charged for the ones that were redeemed.

"Of course, out of the 75 employees, only three were redeemed. He sure saved a lot of money that year," she says. 

People understand that forgoing employee holiday gifts might be required in tough times. But it's far worse to suggest you're just "checking the box" and hoping nobody will notice.

Rule No. 2: Beware of the branding. 

Charles Tran vividly recalls what he describes as the worst business holiday gift ever: an extra-large jacket with a big corporate logo.

"I felt like if I wore the jacket, I'd be a walking billboard," said Tran, founder of, a credit card comparison website. "Plus, it wasn't even in my size, which made the gift feel more corporate and less personalized."

Is it always a mistake to include a logo on a custom gift for clients or employees? No, but the key is to keep it subtle and useful. Ask yourself, would I use or wear this gift?

Rule No. 3: Keep it friendly--not personal.  

Anita Mahaffey is the CEO and founder of Cool-jams, Inc., a San Diego company that makes specialty sleepwear. Among her company's products, she explains, are pajamas for menopausal women.

Mahaffey was surprised when a customer explained that she was buying the pajamas for her boss, who hoped that her "crazy hot flashes, night sweats and other menopausal symptoms" had gone unnoticed.

"In the end her boss thanked her, but ... it could have gone either way," Mahaffey said.

At least that gift-giving experience turned out well. Gail Miller, CEO and chief staffing strategist at Consultnetworx, says that the worst gift she ever saw a colleague give was a bottle of wine ... to a recovering alcoholic. 

Rule No. 4: Re-gift with caution (or not at all). 

Ian Aronovich, president and co-founder of, remembers getting an odd business gift from an employee--some kind of contraption to flush a toilet ... with your foot. Aronovich said it was clear that the employee just felt obligated to give "something."

Margo Schlossberg, a marketing director in Maryland, previously worked for a telecommunications company in the Washington, D.C. suburbs. One year, a coworker gave her a "crystal healing tree" as a present, which Schlossberg found bizarre. Later, her company held its holiday party in a bowling alley and she bowled poorly enough to cost her team the prize of a paid day off.

Blaming the crystal healing tree for the incident, Schlossberg "ran it over with my car."

Rule No. 5: Thou shall not be tone deaf. 

Dan O'Connell worked for an advertising and public relations firm that laid off 80 percent of its employees in one year. When all was said and done, the agency owner announced that there would be no bonuses or holiday party.

In an ill-reasoned attempt to improve the mood, O'Connell recalled, the owner said he wanted to tell them about the great European vacation he and his wife had taken. 

"He then proceeded to give us a 20 minute slide show on Paris, Rome, etc. to cheer us all up," O'Connell said. "I later skipped off with a few clients and started my own agency."