10 Ways to Celebrate Boss’s Day Without Getting the Side-Eye

The challenge of Boss's Day—which falls every October 16—is figuring out how to celebrate without feeling like you're a suck-up.

It's less weird—and less likely to create awkward team dynamics—if someone takes two minutes to get everyone organized sometime before the end of the day on October 15. A joint gift from the whole team shows a unified front, takes pressure off individuals to come up with novel gifts or yet another Hallmark card, and keeps things simple.

Boss's Day is basically the most obvious time for an empty or insincere gesture. You know your relationship with your boss. Leverage what works, share a genuine appreciation, and keep it straightforward and simple. A reliable equation goes like this: "Thank you for all you do," and then cite a specific example that was meaningful to you.

In the traditional work hierarchy, bosses give to their less-well-compensated employees—not the other way around. And it's true, there's something awkward about spending money to honor the person who might control whether you get a bonus (and how big it is) or whether you get your next raise. To avoid the inevitable awkwardness that money brings, try effort instead. A heartfelt note is often worth more than that $20 (or should it be $50? More?) on a basic gift card.

The only reason we have Boss's Day is because, in 1958, Patricia Bays Haroski wanted to celebrate her dad—who also happened to be her boss. (October 16 was his birthday.) She petitioned the U.S. Chamber of Commerce, and here we are today, conflicted as ever about appropriate gifts. The solution? Make fun of the whole thing. Someecards has plenty of Boss's Day options, including this gem: "You're my favorite person to desperately seek approval from."

When in doubt, put your money to better use than another venti latte. If your company's mission aligns with a larger, more noble goal—like literacy, helping the homeless or clean water—then pool the team's money and make an online donation in your boss's name. It's a great way to acknowledge your manager and push forward business goals at the same time.

Sometimes all you need to make a day special is to change up the routine—even just a little bit. Maybe a team meeting can be taken outside. If everyone typically eats a sad desk lunch, make the effort to sit together in the break room or cafeteria. It doesn't have to be much. Small changes can be surprisingly refreshing.

When people share a meal, they connect, which, ultimately, is the goal of most bosses—to have a team that's in sync with each other. Whether it's a low-key potluck or a decadent lunch out (whether or not the team covers the cost of the boss's meal), the point is to spend time, to commune and nourish yourselves with good food and good company.

In other words, don't send yet another email. Email is for "Hey, just touching base …" and "Just circling back about that project." You want this to feel a little more intimate than that. A kind note, in your sprawling handwriting, has that personal touch. Better yet, heed Tip No. 1 and have the whole team sign a card.

This is a tricky one, because it's hard not to look like you're trying to curry favor when you're talking up your boss's accomplishments to their superiors. Done right, though, it's one of the most effective ways to make a difference in a manager's life—and to show both your boss and the C-suite that you understand the meaning of value in a business setting.

The weight of Boss's Day shouldn't just be on your shoulders. In a healthy corporate culture, wins are celebrated from the top—and a day of appreciation, like Boss's Day, can also come from the top. Coffee and doughnuts, anyone? It's really that easy.