Boss’s Day: How to Celebrate (and not Celebrate)

National Boss’s Day is a national holiday that you might not be familiar with. While some people aren’t aware of this celebratory occasion, it’s a good idea to educate yourself on the do’s and don’ts of this holiday to understand how you should handle it in your workplace.


Though it’s a holiday that began with earnest intentions, the concept of a day for employees to celebrate their bosses may pose some questions about appropriate employee behavior.


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When is Boss’s Day?

National Boss’s Day is celebrated in the United States each year on October 16. The holiday began as a chance for employees to express their gratitude to their employers or managers. It’s also seen as a way for the relationship between managers and employees to be strengthened.


Showing appreciation for your boss on Boss’s Day

Even though it sounds like a simple idea, National Boss’s Day may put some pressure on employees concerning office etiquette, but it’s important to remember that this occasion should be fun and celebratory.


How should you show appreciation for your boss? Do you need to purchase a gift? What kinds of gifts are appropriate? The questions an employee may have surrounding the occasion can be daunting. Let’s examine some fitting ways to celebrate a boss who makes you feel valued within the company. Some generic gifts that any boss can appreciate include:

  • Bake a cake or some cookies.
  • Give a bag of their favorite coffee or tea leaves.
  • Give a “Thanks a Latte” gift basket (mug, coffee and a gift card to their favorite coffee shop).

These are safe, appropriate choices for the workplace because they’re professional and impersonal, respecting the boundaries of a work relationship. If you have a more comfortable relationship with your boss and frequently discuss their hobbies or interests outside of the office, you may be able to select a more personalized gift for them, such as:

  • A gift card to a favorite store
  • The book they’ve been talking about wanting to read
  • A TV show box set you’ve previously recommended to them
  • A desk plant for their office if they have a green thumb

If you find it intimidating or uncomfortable to give a personal gift to your boss, either because you don’t know them that well or don’t have a strong relationship with them, consider getting everyone in the office to come up with something together. As a group, you can:

  • Collectively sign an appreciation card
  • Create a thank you video with messages from each department
  • All pitch in $5 toward a larger gift
  • Organize a group outing like a picnic lunch or games night
  • Host an office potluck party during lunch hour on National Boss’s Day

For medium to large companies with multiple departments and supervisors, employees can organize an award night where each boss receives recognition for one of their “best” qualities. This idea involves everyone from the office and ensures no supervisor or manager is left feeling unappreciated. Unique categories for these awards can include:

  • Funniest Boss
  • Chattiest Boss
  • Boss Most Likely to Be in a Meeting
  • Boss With the Cleanest Workspace
  • Boss With the Most Photos in their Office
  • Best-Dressed Boss
  • Most Caffeinated Boss

Keep them light and entertaining, but avoid throwing in awards that verge on disrespect. Also, avoid commenting on people’s appearance for features that cannot be changed, like “Best Smile.” Drawing attention to people’s looks in front of a crowd is bad practice in the workplace and could make people uncomfortable, especially if you’re pointing out a feature they’re self-conscious about.


What to expect as a boss on National Boss’s Day

As a boss on National Boss’s Day, you may be wondering what to do. Unless you’re the head of the company, chances are you also have a boss to celebrate. If not, you can choose to take the day to give back to company employees who support you through their work but aren’t your direct reports, such as the administrative staff. Treat them to a cup of coffee or bring in a tray of treats for a morning or afternoon snack.


As a boss, you should not expect gifts from your employees on National Boss’s Day. It’s inappropriate and unprofessional to insinuate to your staff that you expect them to spend their hard-earned money on you for simply doing your job. If they choose of their own accord to present you with a gift or host a celebration because they appreciate all that you do, you can accept graciously.


It’s important to maintain your professionalism and impartiality on and after this date. If certain employees don’t present you with a gift while others do, you cannot hold that against them or play favorites moving forward. Remember that just because an employee doesn’t give you a gift, it doesn’t mean they don’t enjoy working for you or don’t appreciate you. The reality is that you have no idea what your staff members’ financial situation is outside of the office, and they simply may not have the money to spare for spontaneous gift-giving.


To boost office morale, consider also taking the opportunity to express your appreciation for all that your employees do for you as their boss on National Boss’s Day.


Leave it to the pros

Bosses can consider approaching Human Resources and letting them handle all aspects of National Boss’s Day. HR representatives can inform employees about what is appropriate, provide gifts on behalf of the company to present to the head of each department and oversee a sanctioned company luncheon.


Lessening the load on already hard-working employees ensures everyone enjoys the day and feels more comfortable while improving important relationships within the company.

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