Boss’s Day Gifting How-To Guide

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We celebrate Boss’s Day to acknowledge the work and effort our bosses do every day to help us succeed with our professional goals. We know that sometimes gifting for this holiday can be a little tricky. We’re here to help with some easy tips, tricks, and unique Boss’s Day gifts that’ll make this day extra sweet!

However, before jumping into our Boss’s Day gifting guide, let’s delve into the origin of Boss’s Day and why we celebrate our boss.

In this article:

The Origin of Boss’s Day

Happy coworkers talking with boss

Boss’s Day, also known as National Boss Day or Bosses Day, originated in the United States in 1958. Patricia Bays Haroski registered the day with the U.S. Chamber of Commerce while working as a secretary for State Farm Insurance Company in Deerfield, Illinois. She chose October 16 as the date because it was her father’s birthday.

Haroski’s goal was to designate a day to show appreciation for her boss and other bosses, and to improve the relationship between employees and supervisors. She believed that young employees often did not understand the challenges bosses faced and the dedication they had to their roles.

The idea caught on, and Boss’s Day has since become an opportunity for employees to show appreciation for the hard work and dedication of their supervisors and managers. It is observed annually on October 16, or the nearest working day if it falls on a weekend.

Additionally, Boss’s Day allows us to gather as teams and create an impromptu team building event. As many offices tend to create some isolation, any team building activity helps create more camaraderie and put a smile on your boss’s face.

How to Celebrate Boss’s Day

Coworkers applauding their boss in a conference room

Boss’s Day is a special occasion that gives employees an opportunity to show appreciation for their supervisors and managers. It’s a great way to acknowledge the hard work and dedication of your boss. Here are some tips on how to celebrate Boss’s Day.

  • Say “thank you.” Saying “thank you” is one of the simplest ways to show appreciation for your boss. A handwritten thank-you note or a sincere verbal acknowledgment can go a long way in making your boss feel valued.
  • Give your boss a gift. Consider giving your boss a thoughtful gift to show your appreciation. This could be anything from a small token of appreciation, like a plant or a box of chocolates, to a more personalized gift that reflects their interests or hobbies. Just remember to keep it professional and appropriate for the workplace.
  • Plan a Boss’s Day celebration. If your office culture allows for it, consider organizing a celebration in honor of your boss. This could be anything from a small office party with cake and refreshments to a team outing or lunch. Make sure to include your boss’s favorite things in the celebration to make it extra special.
  • Plan a team project or activity. Another way to show appreciation for your boss is to plan a team project or activity in their honor. This could be a special presentation highlighting their accomplishments, a team-building exercise, or a community service project. Get creative and involve your colleagues in showing your boss how much you appreciate them.
  • Share how your boss has impacted you. Take the time to express your admiration and respect for your boss. Let them know how their leadership has positively impacted you and the rest of the team. It’s important to be genuine and specific in your praise to make it truly meaningful.

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How to Select a Great Boss’s Day Gift

Choosing a gift for your boss can be somewhat difficult. However, Boss’s Day marks the day when you can show your boss that they make a difference. As the authority in celebrating everyday occasions, our team can help you select a great gift for Boss’s Day.

Think Practically

It’s always a good idea to think ahead when gifting — will your boss want to eat their treat now or save it for later? Maybe they’ll want to enjoy a bite or two now, but take the rest home. One tasty choice that works perfectly for this situation include our Swizzle Berries® Mixed Chocolate Box.

Topping Ideas for Chocolate Covered Strawberries

Our Swizzle Berries® are hand dipped to perfection in gourmet, semisweet chocolate, then topped with decadent white Swizzle® so they look and taste spectacular. These sweet snacks are easy for your boss to store in the office fridge during the day and take home after work, which is a win-win situation that they’ll definitely appreciate.

Additionally, think about the office culture. Has it been stressful recently? Conversely, does your boss keep the mood light and fun? Our Bundle Of Cheer arrangement is perfect in either case because it will surely provide some good vibes. (Plus, it includes plenty of fresh fruit and chocolate covered goodies for everyone in the office.)

Bundle of Cheer gift with balloon, fresh fruit bouquet and box of chocolate dipped fruit

Our Bundle of Cheer gift set has everything you need to make your boss’s day extra special. Chocolate dipped strawberries, chocolate dipped pineapple, and an assortment of fresh fruit are all carefully crafted in a keepsake container.

It’s all paired with a delightful box of mixed Dipped Fruit™ that features a flavor for every taste bud. Packaged all together with a fun and cheerful balloon, this thoughtful gift truly is a delicious way to turn any occasion into a celebration.

Personalization is Key

Personalization is a great way to go the extra mile when making your Boss’s Day gift stand out. Cater to their interests, their personalities, or even their personal taste. If your boss is a coffee lover who always looks forward to that afternoon treat, our Thrive Farmers Coffee & Berries Gift Box arrangement is a great choice.

Thrive Farmers coffees and teas are sourced directly from farmers who receive predictable, stable and higher incomes to support their families and communities. It’s how Thrive Farmers is reengineering the coffee industry to break the cycle of poverty, and it’s how you get to enjoy an exceptional cup of coffee while making the world better—together.

Thrive Farmers Coffee and Berries Gift Box

For an extra personal touch, consider creating your own gift. You can create your own dipped fruit box or create your own desserts box, selecting from all your boss’s favorite treats and flavor combinations like chocolate dipped strawberries, mini cheesecakes, fresh-baked cookies, and more.

If you’re looking for something that’ll WOW your boss, our Sweet Appreciation Flowers Bouquet does not disappoint.

Sweet Appreciation Flowers & Fruit Bouquet

An irresistible combination of delicious fruit and fresh flowers, our Sweet Appreciation Flowers Bouquet is a perfectly indulgent treat that your boss will enjoy.

Make It Shareable

If your boss doesn’t mind sharing with the office, choose a gift with a variety of flavors that everyone can enjoy. This will also allow you to split the cost with your colleagues, making it a truly special treat for the whole team.

For example, the Kudos For All You Do™ gift bundle clearly thanks your boss, but includes plenty of goodies for everyone.

Kudos for All You Do gift set with balloons and a fresh fruit arrangement

We can’t think of a more memorable way to thank your boss for all their leadership and guidance than with our Kudos for All You Do gift set. It includes a delectable assortment of fresh fruit, including chocolate dipped bananas, chocolate dipped pineapple daisies, chocolate dipped strawberries, and more.

This delicious gift truly has something for every taste and preference. Plus, it’s topped with a Thank You balloon bundle as an extra sweet way to show your appreciation.

Another great shareable arrangement designed for a group of people is our Delicious Party® Dipped Fruit Delight basket.

Delicious Party

A completely delightful fruit arrangement filled with lots and lots of delicious chocolate dipped fruit is a great last minute Boss’s Day gift that the entire office can enjoy.

Our Delicious Party® Dipped Fruit Delight bouquet features semisweet chocolate dipped (almost) everything: chocolate dipped pineapple, chocolate dipped strawberries, chocolate dipped apples, and banana bites dipped in both white and semisweet chocolate. It’s all arranged with some of our fresh fruit favorites.

This Boss’s Day, follow these steps to choose a gift that your boss will truly appreciate. If you’re still stumped on what to get, give your local store a call, look around the site for countless gift options.

Looking for the perfect Boss’s Day gifting solution? Visit our corporate gifting page to discover all the ways Edible® can help. Happy gifting!

Frequently Asked Questions About Boss’s Day

Is Boss’s Day always October 16?

Boss’s Day is observed annually on October 16. However, if October 16 falls on a weekend, it is celebrated on the nearest working day.

Should I get my boss something for Boss’s Day?

While it’s not mandatory, giving your boss a small gift or card for Boss’s Day can be a nice gesture of appreciation. Consider the company culture and your relationship with your boss when deciding whether to get your boss a gift for Boss’s Day.

What is nice to write in a boss’s day card?

A thoughtful message can include thanking your boss for their leadership and support, acknowledging their hard work, or highlighting a specific instance where their guidance was particularly helpful. For example, “Thank you for your guidance and encouragement throughout the year. Your support has made a significant difference in my work experience.”

How much should I send on a gift for my boss?

It’s important to keep it modest and appropriate. Generally, spending between $10 to $25 is acceptable, depending on your budget and company norms. Group gifts are also a good option to share costs and avoid overspending.