The holidays seem to be filled with societal pressures that push us toward consumerism. That said, there’s something really nice about receiving a gift, especially when it comes from a source you don’t usually expect: work!
There are some unspoken rules and general best practices to keep in mind to navigate this appropriately in most situations.
(1) Gifts Flow Down
Generally speaking, gifts should be given by managers to their direct reports to thank them for their effort over the past year. That means this gift is uniform across all direct reports and that’s essential to ensure there’s no possible evidence of favoritism that one could derive from the gift given. And it’s also important to note that these gifts should be modest (<$50) so that the employees feel comfortable accepting them and not compelled to give their manager a gift in return, since gifts flow top down.
If you do want to gift your boss, again, keep it modest and you may want to consider doing it privately so as not to compel others to feel like they have to do this as well. The dynamics here require sensitivity: the superior makes more money (in most cases) and so it’s a bit unethical for gifts to flow any other way than from superior to their directs. I was once on a team where a teammate was really pushing for us to get a group gift for our boss and it felt very uncomfortable.
(2) Modest is better than nothing, especially for large groups
I once worked for a woman who was tough but every year, without fail, gave everyone in her organization a holiday card with a Starbucks gift card for a nominal amount (I can’t recall but think it was in the $5 – $15 range). I share this because if you think gifting is too hard or too expensive because you have too many direct reports on your team, this is an option to consider. Even a modest gift conveys that you appreciate your team and is a good way to motivate folks to achieve their best.
(3) Try a White Elephant or other group gift-giving
I recognize that one size does not fit all and there can be very large squads out there. If you are in a situation where it’s a really large team, consider a white elephant gift exchange capped to a nominal amount ($15 or so) to encourage creativity without breaking the bank on gifts for every person (instead, you buy one gift). This should be done in conjunction with a celebration for swapping gifts so consider how you might want to bring all these folks together to do the actual exchanging.
This can be a successful way for a team (read: all the folks who don't manage people!) to self-organize around gift-giving. In the past, I've experienced a derivative of this where everyone was required to pull a name out of a hat and that's who they were responsible for gifting. This helps reduce the amount of gift buying that needs to happen and also allows folks to be creative, especially if you keep the gift amount maximum at $10 – $15.
(4) For virtual teams, aim for inclusivity
If you lead a team or are part of a team with folks in multiple locations, think about who might be left out by certain activities and how you can potentially make those folks whole. If you cannot, perhaps it’s best to avoid that activity. I enjoy taking my team out to lunch as an end of year thank you; for the folks who don’t share my office location, I make alternative arrangements when I am in their location.
(5) Don’t overthink it
Gifts for team members should not be as difficult as a gift for an intimate partner! Also, because this is coming from your wallet as opposed to something company-sponsored, it's important to keep costs down. We all shop for a lot of folks for Christmas and I'm sure work colleagues are not the folks we want to be spending the most on. That said, it doesn't have to be too much work; consumables tend to make great gifts that don't break the bank and are appreciated (e.g. a catered team lunch; gift card that can cover a cup of coffee; a <$20 bottle of wine).
That said, it's important to highlight that gift-giving is not a REQUIREMENT at work. There are going to be teams who don't want to participate in a white elephant and you may have too many direct reports for it to be feasible. Or, if you just aren't into it, that's totally okay.
However, for those who do have a manageable number of direct reports (<10 people) and are inclined to take this type of effort, it's a thoughtful gesture that I know from being on both sides of the coin, is highly appreciated.