The Slice

8 Great Ideas to Celebrate National Boss's Day Remotely

February 10, 2023

On or around October 16th every year, offices around the U.S. celebrate Boss's Day. This is an opportunity for employees to let their bosses know how much they appreciate their leadership over the course of the year. How can you celebrate National Boss's Day remotely, though? How can you reach across the digital expanse and let them know that they're doing a great job?

On or around October 16th every year, offices around the U.S. celebrate Boss's Day. This is an opportunity for employees to let their bosses know how much they appreciate their leadership over the course of the year.

If your team works together in an office, there are a lot of fun ways you can celebrate the holiday. You might host a lunch together as a team, have a potluck, play some games, or go out for a happy hour when the workday is over.

How can you celebrate National Boss's Day remotely, though? How can you reach across the digital expanse and let them know that they're doing a great job?

Luckily, there are tons of fun, thoughtful, and interesting ways to display your appreciation. Whether you want to send a gift or engage in some quality time together as a team, working remotely definitely doesn't hold you back from having a memorable Boss's Day celebration.

1. Send Some Goodies From the Team

One really nice way to thank your boss for all of their hard work, fairness, and kindness over the course of the year is to send a physical gift basket and maybe even some flowers. When you work together remotely, it can start to feel like everything is so, well, digital. This is a lovely opportunity to break through the virtual wall and send your boss some fun goodies that will bring a smile to their face.

You can choose a premade basket (you can find such things on Amazon, Etsy, and countless other sites), or you can put one together yourself. Since you and your team are remote, it's a good idea to have one person be designated to collect and send the items you've all decided you'd like to give to your boss.

If you're feeling stuck about what you should put in your gift basket, here are some ideas to get your creative juices flowing:

  • Travel mug.

  • Classic "World's Best Boss" mug a la The Office.

  • A gift card to their favorite coffee shop, restaurant, or store.

  • A framed photo from the last team meetup.

  • High-quality, personalized stationary and nice pens.

  • Warm, cozy socks.

  • Books on leadership or team building.

  • Sweets or snacks, like cookies, chocolate, or chips.

Depending on how well you and your team know your boss, you can make the gift basket more or less personalized. This can be an excellent choice for new bosses you don't know that well, as they'll be sure to find a few things in the gift assortment that tickles their fancy.

2. Share a Meal Together

Just because you and your team don't all live and work in the same city doesn't mean you can't break bread together. Using the power of video conferencing software and a service like Pizza Time, you can celebrate your boss over a delicious meal.

You've got a lot of options when it comes to how to organize a team meal. Maybe you choose to enjoy a team breakfast together, which can be an absolutely fantastic way to kick the day off on the right foot.

On the other hand, maybe you'd like to take a mid-day break with a nice lunch, or maybe you've decided to take it to the next level with a full-on Boss's Day pizza party.

If you're just looking to spend quality time together on Boss's Day, you cannot go wrong with eating together. Researchers from Oxford have even found that the more often people eat with others, the more likely they are to feel satisfied and happy with their lives. One can only imagine just how positive sharing regular meals with your team could be on morale and camaraderie within the team could be!

3. Schedule Some One-on-One Time

Being in charge of a team (or a team of teams) can mean that your boss doesn't have a lot of time to spend individually with each employee. One really nice gesture on National Boss's Day is organizing one-on-one chats with every team member.

Of course, you'll want to coordinate this with your boss ahead of time. But with a little planning ahead, you can easily set up a schedule where the boss gets to meet with each individual for five to fifteen minutes.

Employees can either sign up for shifts throughout the day or have their boss set aside a block in their schedule. 

Instead of using this time to talk about business, consider this an opportunity for bosses to get to know their employees better on a personal level and vice versa. If you're not really sure how to approach this type of fast-paced get-to-know-each-other session, consider using some icebreaker questions to take some pressure off.

4. Virtual Escape Room

Do you want to do something a little different for Boss's Day this year? Do you have a sneaking suspicion that the best thing for morale is to engage in a challenging and fun game together as a team?

If so, a virtual escape room is just the ticket. Being a boss can be stressful, and getting the chance to play a fun, interactive game together is an excellent way to show your appreciation. It can also be pretty lonely at the top, so giving your manager the chance to enter a world of puzzles, riddles, and codes with your team might be the best gift.

5. Throw a Happy Hour in Honor of Your Boss

You didn't think we would make it through this list without talking about throwing your boss a happy hour event in their honor, did you?

Virtual happy hours are seriously one of the best ways for everyone to get to know each other better as a team and continue to develop a spirit of camaraderie. Throughout the work week, your boss and your team work hard to keep the ship afloat and forging forward. A virtual happy hour lets everyone let their hair down and relax, decompress, and spend some quality time together.

Of course, there is a lot more you can do during a virtual happy hour than drink and chat (though there's nothing wrong with that!) You might choose to play some radio bingo together as a team, hire a live music DJ to get the vibe just right, or bring in a stand-up comedian to inject a bit of the best medicine into the entire experience.

A team awards ceremony can be a fun addition to a virtual happy hour. For medium to large companies with a bunch of different departments and supervisors, employees could come up with superlatives for each manager. For smaller companies, it could just be a goofy and fun thing to do within the team, where each team member and the boss receive a lighthearted award.

6. Play Some Games

If you want Boss's Day to be an opportunity for your manager to spend quality time with the team, consider hosting a mini-games triathlon. This high-energy event provides a surefire good time for all involved.

If you don't want to engage in a full-on triathlon, there are a lot of other virtual games you can use to set the tone or break the ice during your Boss's Day event.

There are so many awesome benefits of working remotely, but one of the things that can be very difficult is the fact that the team and the boss don't have as many natural opportunities to spend time together and get to know each other. It's easy for things to be all work and no play all the time.

Having a game night or otherwise incorporating games into a Boss's Day celebration is a fantastic way to show your boss that you want to spend time with them as a person and that you realize that there is more to them than just business, business, and more business. It can also have a tremendously positive impact on the team in the long run, as engaging in team-building games can ultimately help create a healthier culture, higher morale, and an all-around better work environment.

7. Enjoy Live Trivia

Is your boss a know-it-all that loves showing off their knowledge? Are they highly competitive and always looking for opportunities to display their high-level skills? If so, playing live virtual trivia might be the absolute best way to celebrate National Boss's Day.

Pretty much everyone loves trivia, so this can be a great event to throw even if your boss is relatively new and you don't know them that well. The whole team will loosen up and have a great time as soon as the trivia rounds begin, and your boss and team members alike will have a newfound sense of togetherness and camaraderie after the fact.

8. Create a Video Tribute

If you don't have time during National Boss's Day to devote to a full-on event between the boss and the team, consider putting together a video tribute that you can send over as a gift.

This is a thoughtful way to let your boss know you appreciate their hard work and leadership. Honestly, you simply can't go wrong with this one.

To make this happen, you'll need to coordinate with your coworkers. In advance of Boss's Day, you'll want to ask all of the other team members to send a short video of themselves where they share a kind and thoughtful message with your boss.

It's a good idea to set a deadline for people to send in these messages so that you can have ample time to string the videos together into a video tribute. That being said, it's pretty easy using a simple video editing software like Apple iMovie to compile them all into a seamless video.

FAQ About Boss's Day

Boss's Day isn't a holiday that everyone knows about, and there is even some controversy around the topic.

Some people fear that Boss's Day can put employees in an awkward position where they feel like they are expected to buy a gift for their superior or otherwise fawn over their boss. However, others feel it is a great opportunity for the whole team to do something different and express their mutual appreciation.

Is Boss's Day Just an Invention of Greeting Card Companies?

Boss's Day is something that has received some pushback and criticism over the years. One of the main oppositional points is that this is just a "Hallmark Holiday," created primarily for commercial purposes.

That actually isn't the case at all, though. National Boss's Day was registered by Patricia Bays Haroski in 1958 when she was working as a secretary for State Farm Insurance. She felt that there should be a day in the workplace dedicated to showing appreciation to hard-working bosses.

At the same time, she thought that the younger employees at the company weren't aware of just how hard their supervisors were working and how challenging their leadership roles were. She thought that this holiday would be a great way to improve relationships between managers and employees within the office.

The day was officially proclaimed in 1962 by Illinois Governor Otto Kerner. As further evidence that this wasn't a Hallmark ploy to sell more greeting cards, twenty-one years went by between the initial registration of the holiday and the first Boss's Day Hallmark card.

When Is Boss's Day?

Boss's Day falls on October 16th and is sometimes also written as Bosses Day or Boss' Day. If the 16th falls on a weekend, though, the closest working day is the day of celebration.

For the years 2023-2026, Boss's Day will fall on October 16th. In 2027, it will fall on October 15th before returning to October 16th for 2028, 2029, and 2030.

Planning a Virtual Boss's Day Event Doesn't Have to Be Stressful

Putting together an entire Boss's Day virtual celebration can sound like a lot of hard work when you consider all of the coordination you have to do between parties that aren't even in the same geographic location. Don't let that push you away from doing something special this October for your boss, though. Instead, let us handle the heavy lifting.

Whether you want to have a team meal, happy hour, virtual experience, or some delicious combination of the above, we've got you covered. If you want to have a great time with your team without the stress of piecing together a virtual event, you can start your order with us today.

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