10 Ways to Celebrate Your Boss, Like a Boss

October 15, 2015

Category: HR Tips & Trends

National Boss's Day

At this point in October, you’re probably planning the perfect Halloween costume and stocking up on all the best sweets. However, don’t forget the other big Autumnal holiday: National Boss’s Day on October 16th!

Boss’s Day has been around for 57 years, but you don’t have to give the same tired gifts that employees first gave half a century ago. Want to ditch those fountain pens and coffee mugs, and modernize your Boss’s Day this year? We’ve come up with a list of the top 10 things you can do (or buy) to show your boss your appreciation—while staying in touch with the new millennium:

Top 10 Ways to Celebrate Your Boss on National Boss’s Day

  1. Share a Meal: As in most areas of life, when celebrating your boss, you can never go wrong with food. Have employees each bring something for a potluck lunch, bring bagels or donuts for breakfast, bake cookies, or even take your boss out for a group happy hour or dinner after work. Enjoying a delicious meal gives your entire team a chance to participate and bond, and it also make your boss feel appreciated.
  2. Decorate Her Workspace: Sneak into the boss’s office (you might need some admin help for this one), and decorate it for National Boss’s Day. Streamers, balloons, jars of candy on the desk–a little nice surprise is a wonderful way to start the day!
  3. Handwrite a Note: Telling your boss you’re grateful for his leadership by way of a handwritten note is a classic way to show you care. Try to be as specific as possible–“You’re a great boss!” doesn’t always sound genuine. Rather, thank him for a time when he helped you out of a bind, or comment on a unique part of his leadership style that you find effective.
  4. Throw a Surprise Party: Get together with your coworkers and plan a surprise party for the end of the day. Have the admins schedule a meeting for your boss in the conference room for the last hour of the day (or some other diversion), and then surprise her with a celebration! You can even create a theme. For example, you could use “The Boss,” and have a Bruce Springsteen-themed party. Play his music, have all the employees wear jeans with bandanas sticking out the back pockets, hang a sign saying, “ [Your Boss] Was ‘Born to Run’ This Team”…you get the idea.
  5. Run it up the Ladder: Unless your boss is the CEO of the company, chances are he has his own boss too. Send an email to his superior to say what a great leader your boss is–and be specific!
  6. Buy Tickets to an Event: Have all the employees chip in to buy your boss tickets to an event you know she’d enjoy–theater tickets, a sports game, a concert…giving the gift of an experience can go far.
  7. Make a Donation: Find a cause your boss is passionate about and make a donation in his name. This shows that you pay attention to what’s important to him, and it gives you the opportunity to help others, which of course, makes everyone feel good.
  8. Give a Gift Card: As with food, you can never go wrong with gift cards. But instead of sticking with the typical Starbucks card, try to find something a little more personal. For example, get a gift certificate from that restaurant your boss has been dying to try but hasn’t gotten to yet, or that fro-yo place down the street where she always goes on her break. This way, you’re giving her something she’ll actually use, while showing her you pay attention.
  9. Bring “Life” to the Office: Give your boss something living for his workspace. No, you probably shouldn’t buy your boss a puppy. But, you can add a little spice to his space by buying a succulent, a miniature terrarium, or a small desk plant. This gives him something nice to look at and something to take care of (with minimal effort).
  10. Support Her Hobbies: Giving your boss something suited to her hobbies keeps the gift personal without being inappropriate. For example, if she’s into hiking, you can get her a book on the best trails in the country. Or if she’s a dedicated yogi, get her a new yoga mat. If you’re not sure what your boss likes to do outside of work, you can get her something to use on-the-job as well. If she travels often, for example, you can get her a travel “survival pack” with sleeping masks, ear-plugs, a guide to tipping policies in other countries, etc. These items will mean much more to your boss than a fountain pen or paperweight, but will also be of practical use.

Ultimately, your Boss’s Day gift shouldn’t be an exercise in sucking up. If your boss has genuinely been a great asset to you, your work, and your career, take the time to do something personal, and let her know you appreciate her. If you aren’t that close to your boss, consider going in on a group gift.

Self-Employed, Treat Your Self

Another possibility is that you’re self-employed and are, therefore, your own boss. If this is the case, don’t think that Boss’s Day is not for you! Rather, turn it into a treat yourself day! Go out to lunch, splurge on a special coffee drink, and reflect on all the good things you do. Because you don’t work with other employees, it can be especially important for you to do something nice for yourself on this day.

When You’re the Boss, Spread the Thanks

If you are in fact the head honcho, even though the day may be about you, be sure to also make it about your employees. It’s important to be appreciative of their work (and their thanks), so return the favor whenever possible.

Most importantly, have fun with the day! Make it about team accomplishments, highlight what makes your boss unique, and keep it fun and fresh to celebrate this Boss’s Day, like a boss.


As a writer, Catlyn enjoys helping to demystify HR and compliance for business owners and HR professionals nationwide. She's also finalizing her PhD in Philosophy and enjoys spending time with her dog, Dottie.

Category: HR Tips & Trends

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