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15 Thoughtful Boss Day Ideas to Show How Much You Appreciate Them

By Preethi Jathanna

Senior Writer for HR and Remote Work

Reviewed by Kara Funk

Senior HR Consultant, People & Culture

Boss Day

There are multiple posts and occasions about organizations appreciating and motivating their employees, but it is a rare sight to see bosses, managers and supervisors getting thanked for their hard work and dedication. Boss Day is an opportunity to celebrate your boss and show them how much you appreciate them. Appreciation should flow both ways, but often we default to employee recognition and not the other way around. Celebrating Boss day provides an opportunity to let our managers know that we are grateful for them, and creates fond memories for both the boss, and the team under them!

On this Boss Day, we have 15 thoughtful ideas to ensure your boss knows how much you appreciate them.. Keep reading!

Struggling to find the right words to tell your boss how much you appreciate them? We’ve got an in-depth guide to help you out, including samples and templates you can use to write the perfect note.

Read our article on welcome messages for new boss for helpful tips and examples to make a positive and lasting impression on your new leader.

1 What is Boss Day?

What is Boss Day

Bosses Day or National Boss Day is celebrated annually on 16 October, prominently in the United States. The event dates back to 1958, when an employee of State Farm Insurance Co. in Illinois, Patricia Bays Haroski, decided to register the holiday to not only honor her boss but also create an opportunity for all employees to honor their bosses. She believed that Boss Day would be instrumental in improving employer-employee relations.

While it may have emerged as an American holiday, countries like India, Lithuania, Australia, and South Africa have also begun to observe the same. If it falls on a weekend, it is celebrated on the working day closest to it. 

2 Why is Boss Day Celebrated?

Why is Boss Day celebrated

Boss Day is observed as a day for employees to thank their bosses and show appreciation to them for their time, effort and dedication to their team. The employees take it as an opportunity to acknowledge the hard work and challenges faced by their managers who guide and support them throughout the year. 

Gratitude is a natural bonding agent and Boss Day is an opportunity to strengthen bonds between managers and their direct reports. Managers often take on additional work in ensuring their direct reports are not only supported in their work but also have an opportunity to grow and develop. This day affords an opportunity to recognize those efforts that make a big difference in the company. 

Whether you’ve gone back to the office or worked from home for some time, Boss Day acknowledges the efforts and professionalism of your manager, senior, or team lead. It's also a great way to have some fun with them!

3 How to Plan for Boss Day?

How to plan for Boss day?

3.1 Brainstorm Ideas for Gifts and Activities

Gather your team and think of Boss Day celebration ideas you could do or what kind of presents you could give to show your appreciation. This depends on what the boss usually likes doing and the kind of things they like as gifts. Make a list and narrow it down to the best ones.

3.2 Schedule the Activity in Advance

If it is an activity that needs a prior booking, such as a Spa appointment or a pottery class, check the calendars of the team and your boss and inform everyone in advance. Send a calendar invite to know the confirmed number of people participating.

3.3 Include Remote Teams

Include remote employees in the Boss Day celebration ideas as well by using a video conferencing tool like Zoom and scheduling a call with them and the boss. They could send in their wishes and signatures in an e-card and email it to the boss, or they could be a part of the virtual festivities by being on a video call.

4 10 Ways to Celebrate Boss Day in Office

4.1 Boss Day Bingo

This is one of the creative Boss Day ideas to throw the spotlight on your boss. Create a Bingo card and fill the boxes with random and quirky experiences about your boss. You could write things such as:

  • My boss taught me a new skill
  • He/she wrote me a review
  • My boss played a prank on me
  • I lost a bet with the boss
  • My boss and I accidentally matched outfits
  • My boss caught me slacking

Hand out these cards to the employees and ask them to tick the boxes they have experienced. What’s more, ask everyone to share their experiences with the boss and the group together!

4.2 Lip Sync Videos

Lip sync videos involve an individual or a group dancing and lip-syncing to famous songs on apps like TikTok or Instagram. To create a lip sync video, corral your team for a fun lip sync video on boss-themed songs like The Boss by James Brown, Superwoman by Alicia Keys, Like A Boss by Chase Guehring, Eye of the Tiger by Survivor, and many more. Pull your boss in to join on the mic for one as well! 

4.3 One-on-One Club

Oftentimes the boss doesn’t get to connect and spend time with the staff for non-work reasons. On the Boss Day, set aside a block in your boss’s schedule and select a spot from your team members’ schedules and such that everyone gets a 10-minute one-on-one chat with the boss. Use a cloud-based calendar like Google Calendar to schedule the appointments.  It would be even better if you could do the casual 1:1s outside of the office - a local coffee shop would be ideal!  Keep some icebreaker questions/ games ready, if required.

The only rule of the one-on-one club is - strictly no work talk allowed!

4.4 Plan a Heist!

Plan a Heist!

For all the Brooklyn 99 fans out there, get ready to partake in a heist with your boss! Plan the activity in advance and ensure your team members, along with your boss, are available for a couple of hours to participate. Divide everyone into two or more teams.

Just like a treasure hunt, the rules of the heist would be to retrieve an object before the other team does within the stipulated deadline. The object is to be hidden in the office premises by the host, and clues can be given at different intervals if required. Get your creative and competitive juices flowing on Boss Day with a heist!

4.5 Host a Team Breakfast

What’s better than hosting the most important meal of the day for the most important person in the room? One of the National Boss Day ideas is to host a breakfast with your boss and your team members. Include healthy and nourishing dishes like eggs, oatmeal, pancakes, bagels, cereals, yogurt, and coffee, tea, and juice. Get the team more involved in the event by hosting it as a potluck!

4.6 Create a Custom emoji/ GIF

GIF makers now’s your time to shine. Dedicate a customized emoji or GIF to your boss on Boss Day. Select an awesome photo of your boss to create a sticker or a video where your boss is laughing to use as a funny GIF in conversations. You could also use an app and create a customized emoji of your boss with Bitmoji or Zmoji. Upload the emoticon on your team communications channel like Slack. Create one with their thumbs-up pose to increase motivation while at work!

4.7 Boss’ Day Out

Boss’ Day Out

To create a more meaningful and pleasurable experience, take your boss out for a day of relaxation and entertainment on Boss Day. Some examples of the activity can be:

  • A Spa and Salon appointment
  • A 4D movie experience
  • A museum or art gallery tour
  • Team games like Laser Tag, Go-karting, Paintball
  • A round of golf
  • A pottery session 
  • A picnic in the park or by a lake

These team outings create wonderful memories and team bonding experiences and are easily one of the best ideas to celebrate Boss Day.

4.8 Video Tribute

Video Tribute

A great Boss Day idea is to create videos of you and your team members thanking the boss and sharing memorable experiences with them. This would add a heartfelt vibe and a personal touch to the video. Get some of your colleagues to dress up as the boss for an overall fun experience. You could put together a JibJab video card for some sure-fire laughs. 

4.9 Appreciation Blog Post

Ask all the team members to write a paragraph about their boss. You could write the blog post in an interview format and include questions such as:

  • Write a few qualities about your boss that you appreciate the most.
  • What have you learned from your boss that has made a difference in your life?
  • Something you want to really thank them for.
  • What is the one positive thing you’ve always wanted to tell your boss but never had the chance?
  • If you were called to give a reference for your boss, what would you say?
  • Imagine this is the last time you’re meeting the boss, what would you want to ask them?

Collect the responses and build them into a blog post in a cohesive manner to publish on your company’s internal blog or magazine. This gift to your boss on Boss Day is surely going to turn on the waterworks in them!

4.10 Award Ceremony

Award ceremony

This Boss Day, take the opportunity to let your managers know how much you appreciate them by having an award ceremony. Create light-hearted and quirky trophies, medals, or badges such as:

  • Best Dressed Boss
  • The Coolest Manager
  • The Funniest Manager
  • The Record for the Most Coffee Consumption Per Day award
  • The Smoothest in Times of Crisis award
  • The Always Got Your Back award

Employees could also share their stories and experiences as the reason for presenting the particular awards to make the ceremony more personal and authentic.

5 What Can I Get My Boss for Boss Day?

5.1 Send a Card

Send a card

Sending cards is the most simple and time honored way to show appreciation. Your boss will enjoy it, especially if they like low-key celebrations. Cards give a personal touch to the event. Some ideas are:

  • Send a cool group greeting card signed by all members of the team.
  • Send fun video digital e-cards like these: American Greetings, Doozy Cards, Jib Jab, and Blue Mountain
  • Create a ‘Word Cloud’ with words from all team members that describe the boss using the Word Art website.
  • Create a photo card of fun pictures of the team and the boss on the Collage website. A cool idea is to photoshop your boss on the throne from Game of Thrones!

    5.2 Gift a ‘World’s Best Boss’ Merchandise

    Go the ‘Michael Scott’ way by gifting your boss some cool merchandise with the words ‘World’s Best Boss’ on it this Boss Day. It could be a coffee mug, a glass water bottle, a t-shirt, a keychain, a pen, a mouse pad, or even a laptop bag. You could also add a caption of a phrase they constantly use at the office, something like “You rose to the occasion”, or “I will handle this”. Including their picture or caricature on the merch could add to the excitement and fun!

    5.3 Gift Basket/ Care Package

    Gift basket/ care package

    A traditional gift basket is one of the best ways to show your appreciation to your boss. Gather goodies like flowers, healthy snacks, a bottle of wine, dry fruits, and chocolates. Pre-made gift baskets are available from Gift Basket Village, All About Gifts & Baskets, Cookies By Design, and Etsy. You could also make a self-care package with skincare products, or fill the basket with stationery and tech products like earphones, pen drives, hard disks, etc.  The most important part is tailoring the goodies in the basket to your boss’ likes and interests!

    5.4 Food Coupons & Meal Gift Cards

    If your boss is a foodie and loves to try new cuisines, give them the gift of food with coupons or gift cards from different restaurants. You could also give them a subscription to premium access to food delivery apps like Zomato Pro or Zomatol Gold. If coupons and meal cards are not accessible, book them a table at a restaurant in advance for a team lunch to add to the surprise and turn it into a fun team outing!

    5.5 Create a Magazine Cover

    Create a magazine cover

    To show appreciation of the highest order, print a photo of your boss (a stunning one) and use Canva’s tool to create a cool magazine cover. Add their token inspirational phrase as a caption or something funny, and print it. You could also frame it and have it gifted to your boss on Boss Day. Make sure the background complements the picture and the colors go well with their personality!

    6 FAQs

    6.1 How do you celebrate Boss Day virtually?

    Boss Day can be celebrated virtually by:

    • Gathering the team together over a video conferencing tool like Zoom or Teams and inviting the boss for the meeting as the special guest for the evening.
    • For some entertainment, virtual team-building activities can be played or by putting together a virtual office party.
    • A Boss Day e-card with everyone’s signatures can be emailed to the boss.
    • A Boss Day gift basket can be delivered to their home
    • The team can put together a video tribute to show their appreciation and gratitude.

    6.2 What are some of the best ecard websites for Boss Day?

    Some of the best ecard websites are group greeting, American Greetings, Doozy Cards, Jib Jab, Blue Mountain, Canva, SmileBox, and Paperless Post

    You can create your own personalized cards via these sites, and they even have a collection of templates to choose from. Create a static or video card with your team for your boss, and add funny captions/ quotes as well.

    6.3 What are some unique quotes and messages for Boss Day?

    Some unique Boss Day quotes and messages are:

    • Though our journey has just begun, we know that we are going to touch new heights by working in synergy with each other. Happy Boss’s Day to you.”
    • “On the occasion of Boss’s Day, we extend our warm wishes to our new boss, who is going to help us achieve what we have not yet achieved. A very Happy Boss’s Day to you.”
    • “I only bring my A-game because I have such an exceptional coach. Thanks for sharing your best plays.”
    • On your team, there are no roadblocks, only speedbumps. Happy to be on this journey with you.”
    • “You have to shoulder many responsibilities as a boss, and we are sure that you are going to shoulder them all with grit, grace and perseverance. Happy Boss’s Day.”
    • “Employees are happy when they have someone ambitious, motivating and understanding to lead them, and we are happy to have you. Happy Boss’s Day.

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