19 Boss’s Day Activities and Gifts for In-Person and Remote Teams

| Employee Engagement, Team Building
19 Bosss Day Activities and Gifts for In Person and Remote Teams featured image
This Boss’s Day, show your leaders how much you appreciate all their hard work, support, and dedication with these Boss’s Day activity and gift ideas.

Every year on October 16, Boss’s Day is observed as an opportunity for employees to celebrate the strong, caring leaders who create positive outcomes for people and organizations.

And if you’re wondering how to show your leaders you care this year, we rounded up some Boss’s Day gift and activity ideas you can consider.

Whether you work in the office with your boss or you’re part of a remote team, these are easy and meaningful ways to appreciate your leaders this year.

What is Boss’s Day?

Contrary to popular belief, Boss’s Day wasn’t created by the greeting card industry. In fact, it was actually created in 1958 by an executive assistant named Patricia Bays Haroski.

She originally registered “National Boss’s Day” with the U.S. Chamber of Commerce to show appreciation for her boss and as a means to promote office culture by building a relationship between managers and employees.

Fun fact: Haroski decided to observe Boss’s Day on October 16 to commemorate her father’s birthday.

Today, Boss’s Day is observed to recognize the outstanding efforts of great leaders, from small businesses to global corporations and everything in between.

So, if you’re looking for ways to show appreciation for your boss this year, we’ve got you covered.

5 Boss’s Day Gift Ideas

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If your team is the gift-giving type, then these Boss’s Day gift ideas are sure to be a big hit with your leaders and will make them feel valued and appreciated.

World’s Best Boss Mug

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Is your boss a fan of the show, The Office? If so, you can get them Michael Scott’s very own “World’s Best Boss” mug—fully branded with the Dunder Mifflin logo.

While you might not find it at Spencer Gifts, the good news is that they won’t have to buy it themselves like Mr. Scott did.

Create a Yearbook

Ready to get sentimental? Here’s how to do it.

Think about all of the things your boss or leader goes through in the course of a year. Highs, lows, successes, challenges—the good, bad, and ugly.

So, to help them reflect on the best parts of it all, put together a yearbook highlighting their biggest achievements, greatest milestones, and you and your team’s most cherished memories together.

This is something that will stick with them for a long time.

The Destination Bag

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The Destination bag is a cleverly designed two-in-one garment duffle bag that allows bosses to show up to business meetings, celebrations, and other big work events looking like a total boss. It includes a suit compartment and rolls out into a duffle bag that can zip any other items inside. It’s perfect for business trips and work vacations.

A Great Bottle of Wine

If your boss is a wine lover, give them a good bottle of red, white, or rose that they can take home and celebrate with at their leisure.

Or, if they’re not big on wine, consider getting them their favorite bottle of spirits.

While these can be higher ticket items, if each team member kicks in a couple bucks, it can add up quickly.

Make a Donation in Their Name

If your boss isn’t big on receiving gifts, try celebrating Boss’s Day by making a donation to a charitable initiative in their name.

You can either coordinate with them on which one to donate to or you can pick based your knowledge of them as a person.

And, if you want to get the whole team involved, you can even enlist a charitable team building activity so you can all give back as a group. You’ll find a number of them in the next section!

6 In-Person Boss’s Day Activity Ideas

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If you work in the same office with your boss, these simple yet fun in-person Boss’s Day activity ideas will make your boss feel appreciated and provide a fun and engaging  team bonding experience.

Boss’s Day Bingo

Want a simple and fun Boss’s Day activity idea? You’ll love Boss’s Day Bingo.

All you need to do is hand out a bingo card to every member of your team (like this Boss’s Day Bingo Card template).

Next, write each item from the card onto individual pieces of paper and drop them into a hat. From here, assign one person to draw from the hat and announce it out loud to the team.

Each person it applies to will cover the appropriate square on their card—and share the story behind it.

Whichever person fills their whole board first wins!

Domino Effect Challenge

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With an activity like Domino Effect Challenge, your group will split into teams that will need to complete their own respective section of a chain reaction machine. But then, they will also need to come together as a full group to collaboratively assemble their sections into a fully functioning device.  

Host a Team Lunch

Usually it’s the boss who takes everyone out for lunch to celebrate special occasions and milestones. But on Boss’s Day, you can flip this tradition on its head and have the team pitch in to take the boss out.

It doesn’t even have to be a fancy meal. For most bosses and leaders, simply getting out and spending time with their team in a non-work environment is enjoyable enough on its own.

These kinds of team outings really help build employee morale and team comradery.

CI: The Crime Investigators

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Clear communication, critical thinking, and problem-solving skills are among the most critical points of focus for any leadership team, and that’s why bosses loves team building activities like CI: The Crime Investigators. In this game, you’ll need to think analytically and work together to collect evidence, decipher clues, and solve a mysterious and deadly crime. 

Host a Boss’s Day Potluck

Celebrate Boss’s Day by hosting a company potluck where everyone brings their favorite dish—or one that reminds them of their boss! Then, simply sit back, let your boss chat and connect with their team in a social setting, and watch everyone create organic bonds.

Pro tip: In the lead-up to your potluck, circulate a sign-up form so that people can write down what they’ll be bringing to ensure people 

Wheelchairs for Charity

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Doing good deeds has been scientifically proven to reduce stress and make people feel better. That’s why philanthropic team building activities are a big hit among senior executives. Our Wheelchairs for Charity activity fuses philanthropy with real-world learning outcomes to help participants give back while sharpening their business skills. Together, teams will build and test fully functional wheelchairs before donating them to those in need. This exercise is great for helping leadership team members increase their empathy while enhancing their communication and collaboration skills.

8 Virtual Boss’s Day Activity Ideas

For remote teams, celebrating Boss’s Day requires a little bit of thought and creativity. Here are some simply Virtual Boss’s Day activity ideas you can do easily, even from a distance.

Virtual Code Break

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Leaders are constantly faced with complex and outside-the-box challenges. With a team building activity like Virtual Code Break, you and your bosses can become even better equipped to tackle real-world issues by communicating and working together to complete brainteasers and mental exercises.

Create a Video Tribute

Just because you can’t celebrate your boss in person doesn’t mean you can’t share a heartfelt personal moment with them.

All you need to do is coordinate a Boss’s Day video tribute with your colleagues. Simply ask each of your colleagues to send you a short video of themselves delivering a quick message to your boss, then use a simple video editing software like Apple iMovie or even just Canva’s video editor to put them all together.

Virtual Team Pursuit

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Healthy competition can have big benefits in business. With Virtual Team Pursuit, bosses and their teams can can get to know each other, compete, and break down barriers in a low-pressure environment. In this activity, your group will break out into remote teams that will earn points by tackling physical, mental, skill, and mystery challenges as they compete to be crowned the champions.

Send a Fun Card

Services like JibJab allow you to send fun animated cards that are sure to get a laugh out of your boss this Boss’s Day.

Or, if you want to do something simpler, you can circulate a digital card for your entire team to sign remotely. At Outback, we use Group Greeting for this.

Virtual Clue Murder Mystery

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When it comes to building collaboration, communication, and problem-solving skills, Virtual Clue Murder Mystery is a perfect team building activity for senior executives and their team members. It will allow your group to exercise these key skills in a relaxed. In this game, your team will need to put their heads together to use clues, case files, and logic to crack the case of a mysterious murder.

Profile Them Publicly

Consider profiling your boss on your company’s blog or social media. Offer your customers, colleagues, and anyone else reading a better understanding of who your boss is, what makes them so special, and why they make such a profound impact on your organization and its people.

Host a Virtual Boss’s Day Happy Hour

In many instances, the only time bosses and leaders really get to engage with their team is during work hours and formal meetings—especially when they work remotely from their colleagues.

So, finding ways to help them socialize in a less business-centric setting is a great way to help leaders connect personally with their employees.

And what better way to do that than with a Boss’s Day virtual happy hour?

To make it extra fun, you can incorporate a few games.

Water or Not Water 

Have you seen the HBO show Run? It’s what made this game really popular. If you haven’t seen it, don’t worry. This game is incredibly simple. 

Essentially, all you need to do is have each team member pour a few shot glasses—some filled with a transparent alcoholic spirit and one filled with water. 

During each round, one person chooses a glass and takes a shot. That player then says either that the liquid they drank was “water” or “not water.” Everyone else then takes turns guessing whether they’re telling the truth or not based on their facial expression.  

Virtual Happy Hour Trivia

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This is no ordinary happy hour trivia game. In this activity, you and your team will take a trip to Hamish McDuff’s virtual pub. This hilarious Scottish pub owner is the legendary host of a trivia game with more than 20 category options to choose from, including sports, food and drink, and even celebrity real estate. This virtual pub trivia game is guaranteed to produce plenty of laughs and lift team “spirits.” It might even include a few special surprises.

Up Close and Personal 

Here’s a weird one question, but have you ever looked at something really closely zoomed in? Believe it or not, it can be really tough to recognize everyday items when you zoom in close on them. And therein lies a fun game!  

Find some photos of items closely zoomed (you can find a bunch here). Then, share your screen with your colleagues and go through different photos, seeing who can guess each item correctly. Give a point for each correct response and, once you’re out of photos, see who got the most right. 

You can take this idea to the next level by sending all of your participants a Happy Hour Box before the virtual event.

This kit includes snacks, icebreakers, a handy tumbler, and a cocktail kit. Just add some hard stuff, and you’re all set for a good time. Take this quick 60-second quiz to get personalized options for your team.

Want even more ideas for your Boss’s Day social? Check out this list of virtual happy hour games for workgroups.

Virtual Game Show Extravaganza

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With Virtual Game Show Extravaganza, your team can go head-to-head in your very own virtual game show. Together, you’ll need to tackle photo and trivia challenges covering everything from pop culture to politics as you compete to earn points and be named winners. An activity like this is a great way to help boost your communication skills and connect in a different way.

Looking for even more ideas for team building activities for your boss? Check out our list of team building activities for CEOs and senior leadership.

Boss’s Day is a great way to celebrate your leaders on October 16th, but it doesn’t have to be the only day. Just like great employee engagement is something that takes place all year round, the same applies to appreciating your boss and all of their hard work all year round.

So, take the chance to do something fun for Boss’s Day, but consider ways to make sure they feel valued and appreciated during the other days of the year too.

Does your organization do anything to celebrate Boss’s Day? If so, let us know what kinds of things you do in the comments section below!

Learn about team building activities for Boss’s Day.

If you’ve got questions about team building activities that can make Boss’s Day even better, reach out to an Employee Engagement Consultant.  


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