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The Challenges of Showing Appreciation on Boss's Day

Do you get a gift for your supervisor, or is that … awkward?


​You like your boss. You appreciate that she gives you a flexible schedule, frequent shout-outs and criticism that's actually constructive.

But with National Boss's Day observed on Oct. 16, you feel weird about dropping a Hallmark card on her desk, even though you know some of your colleagues plan to do that. To you, it feels like fawning.

To prevent employees from feeling awkward or obliged on such a day—or even, say, on a boss's birthday or work anniversary—is it better for the company to take the lead by having leaders, instead of rank-and-file workers, arrange appreciative cards, gifts or meals for supervisors? 

​"Something like Boss's Day should not be left in the hands of employees alone," said Cord Himelstein, vice president of marketing and communications for employee recognition company HALO Recognition. "The company really needs to step up and take the heat off of front-line employees by celebrating Boss's Day officially and offering a token reward or gift. Taking the lead in this manner eliminates confusion as to whether the boss was properly recognized."

Patricia Bays Haroski laid the groundwork for National Boss's Day while working as a secretary for her father at State Farm Insurance Co. in Deerfield, Ill. She honored her father on his birthday, Oct. 16, by registering the secular holiday with the U.S. Chamber of Commerce in 1958. In 1962, Illinois Gov. Otto Kerner proclaimed the day an official holiday. By 1979, National Boss's Day was generally recognized throughout the United States. Within the past decade, the day has been celebrated to some extent in Australia, India, Ireland, South Africa and the U.K.

Yet critics say the day makes employees feel obligated to purchase gifts for supervisors who have more power and generally make more money. And what about how some managers view the day: Do they question a worker's motives if the worker gives a gift? What is appropriate and inappropriate? If a boss doesn't get any cards or gifts, does that disappoint her or make her question her effectiveness as a boss?

Keep It Real

​Cynical as it may sound, some managers may view cards and gifts from subordinates as ingratiating, while others may feel slighted if workers don't somehow acknowledge the holiday, said Paul White, a psychologist in Wichita, Kan., who writes on relationships in the workplace. He is co-author of four books, including The 5 Languages of Appreciation in the Workplace (Northfield Press, 2014).

"There's a sort of damned if you do and damned if you don't tension, whether it's Boss's Day or a similar day," White said. "As we work with communicating appreciation among team members, this issue does come up."

The context in which a worker shows appreciation, he said, can influence how a manager views a card or gift.

"If [a worker] gives a once-a-year big gift right about the time there's some big decision about a promotion in the near future," that could indeed look like currying favor, he said.

Each employee needs to decide if giving a gift on Boss's Day feels authentic or not, said Audrey Epstein, a partner with The Trispective Group, a workplace training consultancy in Longmont, Colo. She is also co-author of The Loyalist Team: How Trust, Candor, and Authenticity Create Great Organizations (Hachette Book Group, 2017).

"This is really more about how you show up the other 364 days of the year," she said. "A gift that doesn't connect to the real relationship you have with your boss will come across as insincere or sucking up. Do not use Boss's Day as a way to 'fix' your relationship with the boss. If giving a gift feels like sucking up to you, it probably is. Work on what's most important in any employee-boss relationship, which is real and candid communication based on mutual trust and respect."

Consider the Recipient and the Relationship

​White recently celebrated his birthday. His workers gave him cards and gifts, and he was comfortable with those gestures. "If I have a personal and trusting relationship with a team member, it's a nonissue," he said. "But if there's some kind of relational tension or lack of trust, I might feel differently. Also, I think the manager brings something to it: I'm a fairly open, trusting kind of guy, but if somebody is more private or a little closed, [receiving cards and gifts] may be a different experience for them. Some people have a reason not to be trusting of others, just because of their life experiences." 

[SHRM members-only toolkit: Developing and Sustaining Employee Engagement] 

And managers should have the emotional intelligence to not take it personally if some workers feel awkward about showing appreciation on Boss's Day, a supervisor's birthday or the like, Himelstein said.

"Being a manager can be tough on the psyche at times," he said. "As a manager, maintaining genuine connections with complex humans is hard work, and the hardest part is putting your personal disappointments aside. Regardless of how I may feel about an employee showing appreciation, it's unfair to put the responsibility for my personal satisfaction on them. Boss's Day is not a day for me to question the motives of my staff doing something nice for me." 

What’s Appropriate?

​For those who do decide to give cards or gifts, it's best to keep it small and simple, Himelstein said. He suggested taking a look at his organization's quick ideas for Boss's Day.

"It's not something you want to overthink," he said. "A funny card or e-card, a gag gift—even something as basic as offering to buy them coffee in the morning—gets the message of appreciation across. Avoid anything extravagant or expensive that would make colleagues feel awkward. Avoid making a spectacle and do not broadcast your personal thanks to co-workers. Seeking recognition for your own act of recognition is the epitome of insincerity."

Epstein said that such cards and gifts should be symbolic and demonstrate an authentic "thank you."

"I've been in hundreds of leaders' offices, and what they proudly display on their shelves or desks are the meaningful cards written to them over the years or the symbolic gifts—like a picture of the team, something representing an inside team joke—that let them know how they have helped, developed or positively impacted others," she said. "Think about what it is that you specifically value about your boss. Is it how they reacted when you messed up? Is it the way they inspired your best work? Sharing a specific reflection is much more powerful than simply saying, 'Thanks for being a great boss.' "

Let HR Handle It?

​As Himelstein mentioned, some companies may find it best to have HR or the leadership team shoulder the responsibility of arranging appreciative gestures for supervisors.

"The true obligation lies in the hands of upper management to properly recognize managers from the top down," he said. "Have a special managers lunch, create a funny award, write a nice e-mail from upper management."

White disagrees, however.

"[Appreciation] needs to be personal rather than organizational," he said. "A gift is about knowing [a manager] and what they like. Everybody getting the same $25 gift card with the same note doesn't mean much. It's not like you really thought about them. On my team, some of us like dark chocolate and some like milk chocolate. If you get me dark chocolate, it says 'Hey, you're paying attention to me as a person and you know what I like.' A personal touch is important if you're trying to communicate that you value someone."

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