A few Decembers ago, Tray Ross, VP of growth at Corporate Traditions, received a very special gift from his company: the option to choose his own company Christmas present. “I got a backpack that I’ve always wanted, but never really had the budget or had the means to purchase. I still use that backpack almost every single day. And every day I pick that backpack up, I flash back to getting that gift, and the holiday party, engaging with the different members of my team,” Ross said during a From Day One webinar.
That little gift had a major impact: positive emotion. “It wasn’t anything massive. It wasn’t incredible. It’s not going to change the world, but every time I look back, I have immense gratitude for the fact I was able to get that small item,” he said.
Most HR teams scramble to pull together holiday gifts weeks before the deadline and end up with branded swag nobody wanted, last-minute raffles, and a budget that didn’t stretch far enough. Ross discusses how to build a holiday recognition strategy now, before the rush hits, that scales across your entire workforce, maximizes the value employees actually feel, and makes HR the hero of the holiday season.
Beating the Holiday Season Scramble
Lots of companies fall into what Ross calls the Q4 scramble, trying to plan holiday celebrations or gifts for employees at the last minute, losing hours or work time to logistical planning, running out of room for storage, giving out branded swag nobody wanted, and working with a budget that doesn’t quite stretch far enough. Waiting too long to plan for holiday recognition,including waiting on the leadership team to approve a budget, can lead to overpaying for less and employees feeling like an afterthought.

Ross says August is the perfect time to start planning holiday recognitions, giving teams 60 to 90 days to prepare. His suggested plan of action is to shortlist a tool now that can move as soon as the budget is approved. By September and October, you’ll be ready to move forward, wherever the budget lands. Then, in November and December, you can execute in minutes rather than weeks.
With Corporate Traditions, “you can just upload and send out lists and be able to recognize employees at scale and make a personal impact, even if it’s for three employees or with 3000 or 5000 or 10,000 employees,” Ross said. “We make our money on the back end through our partnerships, so we keep everything dollar for dollar for you, which makes it easy to get approval from finance.”
Available rewards include Gift Card+™, in which employees can select from over 1700 gift card options and enjoy instant fulfillment; GiftYouPick™, in which employees choose their own prizes from over 500 brands; and Grocery Vouchers, which can be especially meaningful around Thanksgiving and Christmas. Both GiftYouPick™ and Grocery Vouchers are de minimis fringe eligible, Ross says, meaning they can stay compliant with the IRS requirements to keep a gift tax-free and off an employee’s W-2 payroll. “The IRS has outlined three requirements for a de minimis fringe gift,” Ross said. “The first requirement is it has to be infrequent, so holiday gifts, birthdays, work anniversaries [all apply]. The second one is that it has to be impractical to track for,” which means generally $100 or less, though this threshold varies by city, county, and state. “The last one is it has to be something specific and tangible, so that’s where the GiftYouPick™ and the Grocery Vouchers come in handy because they’re able to get something specific and tangible that is no longer a cash equivalent.”
Corporate Traditions makes it easy to ensure gifts are actually fulfilled and enjoyed, he says. “You have digital copies of every single code that was issued for the employees for the Gift Card+™ and the GiftYouPick™, so you can just reissue those as many times as you need without ever being charged again, as well as being able to send reminders as often as you need,” Ross said.
The Holiday Playbook
Ross offers a playbook for creating gift programs that are simple, meaningful, and memorable. Start by choosing a tool that can move quickly, since you rarely control when the budget is approved. Instead, focus on being ready to act as soon as it is available. Next, choose the moment you want to recognize, whether that’s Thanksgiving, December, or both. Rather than sourcing a single gift and guessing at people’s sizes or preferences, give recipients a choice and let them pick for themselves. Finally, keep the process simple: upload your list once, with no minimum order or contract required.
This streamlined process can help you avoid hours of vendor calls, reviewing quotes, making spreadsheets of preferences, storing items, chasing down who got what, and reconciling piles of receipts. Instead, you can focus on what really matters for the business. “It takes a lift off the HR team,” Ross said. “You can now spend time developing your people, taking care of the people, and building the business and building your culture, rather than dealing with all of these logistics and things that honestly sometimes are just a time suck, especially when a vendor changes pricing last minute or those types of things.”
But don’t minimize the importance of intentional holiday gifting among other HR strategies: it too can have a major impact. “Employers are spending fortunes on retention strategies, but I’ve had friends in the recruiting space, and they talk to different employees about why they’re leaving or why they’re looking at different jobs. And they tell me one of the common threads that they’re promised certain things, even small items or opportunities, and they never come to fruition,” Ross said. “We need to keep true to those small promises, even though they are small. Staying true to them will help retain our employees and make it easier to keep them, especially around the holidays.”
That’s because holiday gifts are tied to memories and emotions, the things that make us human. “Most memories we have are attached to the emotions that we have,” Ross said. “If you can create more emotions, and if we can allow employees to choose exactly what they want, it fosters more of those positive emotions, which then lead to gratitude [and] appreciation.”
Editor’s note: From Day One thanks our partner, Corporate Traditions, for sponsoring this webinar.
Katie Chambers is a freelance writer and award-winning communications executive with a lifelong commitment to supporting artists and advocating for inclusion. Her work has been seen in HuffPost, Top Think, and several printed essay collections, and she has appeared on Cheddar News, iWomanTV, On New Jersey, and CBS New York.
(Photo by dikushin/iStock)
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