A Holiday Gift for Your Boss: It’s Never Easy

Experts say the tide is changing on what to get (or not get) the boss in the remote-work era. But this decision can be steeped in anxiety.

After a busy year of interacting with his manager and department leader mostly through Zoom, the executive wondered what on earth to give them as holiday gifts. And then how to deliver the gifts: to mail them to their home addresses? Or to leave them on their rarely used office desks?

Norms around gift-giving are changing, following years of remote work and increasingly diminishing face time with supervisors. Back before the pandemic, a survey of 1,000 workers in late 2019 found that nearly two-thirds of them got their bosses gifts, with more than half paying north of $30 for each one. But now, holidays are becoming increasingly separated from the workplace, with just 56% of companies holding holiday parties last year. The result, say experts, is that holiday gifts for bosses may become a relic of the past.

“I tend to be uncomfortable with boss gifts,” says Maria Amato, senior client partner at Korn Ferry. “I worry that they’re too close to the appearance of bribery.” She is far from alone. Experts say that the risk of appearing to curry favor is simply too high, especially when the gift is received by mail or found sitting on a desk, with no in-person interaction.

The move away from boss gifts has been a long time coming. For decades, the going advice was to gift the boss something midpriced that was aligned with their interests. For example, if the boss was a theater buff, two tickets to a show would be appropriate: classy, and neither cheap nor expensive. But now, given that many bosses rarely have time to discuss their interests with subordinates, a gift of theater tickets would seem like an overreach into personal life.

Today’s experts suggest thinking through your goal. “Reflect on what’s driving your desire to get a holiday present, and your relationship with your boss,” says Akiva Marder, associate principal at Korn Ferry. For example, are you trying to express appreciation for the boss, or deepen your personal relationship with them?

Experts say that you can never go wrong with a thoughtful handwritten card, ideally one featuring a family photo. The trick is to make the card unique and specific. “Nothing is worse than generic cards from those you work with,” says Marder. The message on the card could range from an appreciation of a recent event to discussion of a shared interest, as long as it will be meaningful to its recipient.

If a boss who makes more money than you do seems to expect a gift, experts agree you should avoid spending more than $15 to $30. “Don’t try to impress—you likely will do the opposite,” says supply-chain expert Seth Steinberg, senior client partner at Korn Ferry. He suggests something small that commemorates an important moment from the boss’s year, whether work-related or personal. For example, a $15 kitchen gadget is appropriate for a boss who recently moved to a new home. The price tag is decidedly not the point. “The best gift I ever received was shortly after my dog died,” says Amato—a simple holiday ornament engraved with her pet’s name, Oreo.

Going forward, one solution is to send books as gifts during the year, as they naturally come up in conversation and elicit interest. “A book is tailored to the shared interests of the two of you,” says David Vied, global sector leader for medical devices and diagnostics at Korn Ferry. Giving a book as a gift carries a simple message of enthusiasm to its next reader. 


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