What Bosses Give for the Holidays – Mary T. O’Sullivan

By Mary T. O’Sullivan, MSOL

“I will honor Christmas in my heart and try to keep it all the year.” – Charles Dickens

            Everyone seems to be spreading holiday cheer this month, and your boss or company may be no exception. Don’t be surprised if you are handed a card with a small gift attached at lunchtime or if you line up outside a refrigerated truck to receive a holiday ham, turkey, or roast beef. Maybe your boss invites everyone out to for a holiday lunch at a nice restaurant or a catered event inside the executive dining area. Regardless of the boss’s style, year-end festivities are perennial work gatherings to celebrate the holidays as a group.

            I’ve attended many of these celebratory occasions throughout my career, and some stand out more than others. One year, the boss invited everyone to a prime rib luncheon complete with table service inside the company headquarters. It was a delight. Every year I attended; employees received a beautiful Swarovski crystal Christmas ornament. We found out that each ornament was worth $70! Those were the classiest work gifts I’ve ever received.

            Another year, the big boss engaged other employees to give out thermos type coffee mugs that actually kept the coffee hot! I’ve also received stadium blankets, and sweatshirts, long sleeved tees, and pens with the company logo attached. Each time I was pleasantly surprised at the quality and durability of the gift. So, for all their cultural flaws, apparently many companies show that they can be most generous around holiday time. Who wants to be known as the “Grinch”?

            After almost two years of social isolation, people are ready for their in-person office holiday get togethers, but I’ve heard of these much-anticipated gatherings being canceled due to health concerns, specifically COVID and its new variants. In this case, different ways to celebrate are an option. We’re all sick of Zoom meetings by now, and who wants to celebrate alone, all dressed up in front of a screen. Best if the boss decides to give out his annual token of appreciation via regular snail mail. It’s sure to be a lot of extra work for those who need to wrap and package up the gifts, but isn’t that what digital gift cards are for?

            With a mailed or digital gift, the dangers of bad behavior at these parties becomes a non-issue. Better for anyone who quells their nerves with alcohol or accidentally bumps someone in the mouth and knocks out a tooth (true stories!).

            For companies that chose to host in-person festivities, accommodations are made for those who wish to avoid close quarter crowds. Everyone receives a gift card, whether attending in person or not. No one needs to feel left out with such an egalitarian approach. I have to assume they skip the raffle tickets, because the logistics of pulling numbers and delivering gifts would be impossible.

            Some companies are skirting the whole party-and-gift-giving-during-COVID conundrum by allowing employees to take extra time off to spend with their families. “I believe that we should work to live, not the other way around,” states one company founder. Others are recognizing the spirit of gift giving by asking employees to give to charities on Giving Tuesday, which was November 30 in 2021, or recognizing International Volunteer Day by doing volunteer work, which this year fell on December 5. The company Employee Resource Groups (ERGs) will host activities related to their focus, whether it be veteran affairs, minority education, women’s groups, or diversity, equity, and inclusion. These people get the satisfaction and joy of giving back rather than receiving.

            Isn’t that what this season is all about anyway? It suggests the Biblical quote, “it is more blessed to give than to receive.” (Acts 20:35) That’s the best gift of all.

            “When we give cheerfully and accept gratefully, everyone is blessed.” – Maya Angelou


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Mary T. O’Sullivan, Master of Science, Organizational Leadership, International Coaching Federation Professional Certified Coach, Society of Human Resource Management, “Senior Certified Professional. Graduate Certificate in Executive and Professional Career Coaching, University of Texas at Dallas.

Member, Beta Gamma Sigma, the International Honor Society.

Advanced Studies in Education from Montclair University, SUNY Oswego and Syracuse University.

Mary is also a certified Six Sigma Specialist, Contract Specialist, IPT Leader and holds a Certificate in Essentials of Human Resource Management from SHRM.

Get Mary’s New Book: The Leader You Don’t Want to Be: Transform Your Leadership Style from Command and Control to Transformational Visionary