Got a Boss? We’ve Got Boss Day Ideas!

National Boss’s Day is coming up and we’ve got just the tips to make sure you feel perfectly prepared and genuinely appreciative when National Boss’s Day comes knocking on your door (or popping up in your calendar).  

What Is the Best Boss Day Etiquette? 

When you think of National Boss’s Day you’re probably hoping to honor an awesome boss or supervisor with an appropriate gift or communication. At the same time, this is your boss we’re talking about, so there’s perhaps a degree of concern about avoiding any potholes, pit falls, or faux pas attached to telling your boss how great they are.  

For one thing, what if they’re not? What if National Boss’s Day is filling you with dread and you’re looking desperately for a Hallmark card to get you through this most Hallmark-y of occasions? 

On the National Boss’s Day flipside, what if you adore your boss? What if your boss is also a friend, mentor, and all-around awesome person who promotes your growth and inspires you daily? And what you really want to do is show up to the office bearing all manner of gifts, including a new puppy, gold watch, and lifetime supply of snacks and espresso drinks? But then you realize this just might come across as marginally sychopantic at best, and completely unprofessional at worst. 

Last but certainly not least, what if you’re just not the extroverted, “Surprise! Brought you your favorite donut!” type of person? Some of us are shy, especially when it comes to celebrations in office settings. Is there no way around the Boss’s Day awkwardness for us? As a matter of fact, there is indeed a way (or two) around it!   

Read on, take heart, and have no fear! Our Boss Day ideas are designed to make sure you hit a homerun, no matter what your supervisor situation looks like.   

Tried and True: Coffee and a Card 

Surprising them with a little something special, like their favorite Frappuccino or classic drip, is a great way to recognize an awesome boss. 

Actions Speak Louder than Words: Lighten Their Load by Taking an Extra Task 

Your boss has a lot on their plate, and taking something off of it for Boss’s Day might just be the best gift ever. Maybe they’ll be able to take off early, or complete a project ahead of schedule and look like a rock star in front of their boss. 

No Need to “Reply All”: Low-Key Is Top-Notch  

Whatever you do, keep it simple and discreet. This way, your sincere appreciation is the focus, and your co-workers won’t feel pressured to do or spend outside their comfort zone. 

The More the Merrier: Join Forces for the Most Fun  

If your boss has multiple direct reports, or there are several supervisors in your office, consider having a group celebration. Could be a potluck, catered lunch, or quick sweet-focused gathering at the end of the work day where all bosses are given a round of applause and a few fun gifts.  

Quiet Type? Email Is A-Okay 

If you’re working remotely, if your style is non-verbal, or if you just aren’t really into these types of occasions, a simple email will work just fine. Consider something like this:  

  • Dear [Boss]: I just want to send a quick note to let you know that I enjoy working on your team. I’m learning a lot and I appreciate your guidance, support, and encouragement. Enjoy Boss’s Day! Sincerely, [Employee] 

How Do I Recognize Boss’s Day If My Boss and I Don’t See Eye to Eye?  

Putting National Boss’s Day in Perspective

Boss’s Day is an opportunity to look at what you get and how you benefit from your supervisor. This isn’t always a straightforward equation. You may have the best boss ever (most are kind, awesome, inspiring leaders, and that’s, in fact, why they’re supervising others).  

But the best boss for someone else might prove problematic for you. You might find your boss difficult to connect with, difficult to please, inflexible, or all of the above. How, then, do you recognize the day while still being sincere? Well, don’t feel like a phony or count yourself out of National Boss’s Day just yet!  

Did you know that we learn the most from situations where we struggle? This is the neuroscience-based concept of “productive struggle”. Your situation might be tough, but you’re probably learning some great lessons about how to deal with seemingly untenable situations and interpersonal dynamics.  

So when you bring in that cold brew for your boss or hit “send” on that complimentary email, express gratitude for the learning inherent in the ongoing dance that is the boss/employee relationship. 

What Are Some Appropriate, Affordable Boss Day Gift Ideas?  

If you’re putting together a National Boss’s Day celebration for your business that involves multiple supervisors, consider personalizing a bundle of gifts in honor of the event. Here are some winners that boast a low minimum order quantity and budget-friendly prices as well: 

Mrs. Fields® Cheer Cookie Gable Box: Start National Boss’s Day off with a box of cookies on each super supervisor’s desk. These work great for larger companies and group celebrations.  

The Royal Tin with Cookies or Brownies: The bosses in the office don’t have to share, but they might just be inspired to when they see this generously stuffed tin of sweets! 

Thank Cube Cookie Tower: Show boss appreciation with a cookie tower that has a cookie option for every palette, and “thank you” expressed in four different languages on the sides. 

The Bodega: All that’s missing is the wine! This luxury wine accessory gift set includes an opener, two wine stoppers, a pourer, and a thermometer. Having a special dinner in honor of the boss ladies and men? This set makes the perfect parting gift. 

Rising Star Paperweight: Recognize all the awesome bosses in your company with their own glass paperweight, customized for the occasion.  

elleven™ Zippered Padfolio: Every rock star boss deserves a top notch padfolio. This one includes your customized messaging and is presented in a gift box that’s perfect for gifting on National Boss’s Day 

Cross® Calais Satin Chrome Ballpoint: When only the finest will do, Cross® comes through. Every supervisor is sure to feel special with every note taken when you recognize National Boss’s Day with this sophisticated pen.   

Now you’re ready to celebrate Boss’s Day like a boss. So sit back, smile, and enjoy your status as the thoughtful, awesome employee that you are! 

Karleen Andersen

From marketing tips to product recommendations, I’m here to help small businesses be their best.

Published by
Karleen Andersen

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