The Gifting Guide for the Thoughtful Boss — 5 Tips - Senior Executive
Employee Benefits 4 min

The Gifting Guide for the Thoughtful Boss — 5 Tips

Execs can boost morale and show appreciation with thoughtful gifts during the holiday season. Here are five tips to help you get it right.

by Matt Robinson on November 4, 2021


  • Thoughtful gifts this holiday season can bolster morale

  • Look for personalized and high-quality physical gifts

  • Consider giving experiences to teams — both in person and online

  • Set a standard price to avoid the perception of favoritism

With the holidays right around the corner, executives are looking for ways to recognize their employees with thoughtful gifts. However, according to many executives, a fleece vest with a company logo may not be enough to show gratitude.

In what has been deemed “The Great Resignation,” showing appreciation for employees is more important than ever. According to a 2021 survey from Microsoft, 46% of employees are considering making a career transition in the next year. Research from McKinsey finds two factors have led to increased resignations: employees didn’t feel valued by their organization (54% of respondents) or lacked a sense of belonging at work (51%). 

Thoughtful gifts offer opportunities to build that sense of appreciation and community. Here are five tips for executives looking to give the perfect holiday gift. 

1. Tailor Gifts to Employees’ Interests 

“When developing a corporate gift program, [understand] that a one-size-fits-all approach isn’t the best way to reward or recognize employees,” says Jocelyn Thompson, the CEO of WorkVision Consulting which specializes in diversity, equity and inclusion. 

Daylene Jane Alliman, who runs her own workplace consultancy, also suggests staying away from clothes, jewelry, flowers, and candy. These gifts, she says, may not fit an employee’s taste. Instead, strive for gifts that show you are paying attention. 

For example, if your colleague likes fishing, give them a fly-fishing weekend at a hotel. Or, if your budget is lower, consider a fishing rod. Does the recipient love animals? Make a charitable donation to the World Wildlife Fund in their name.

Software solutions like Workhuman and EvaBot can help executives keep track of employees’ interests and make personalized gift recommendations. 

2. Find High-quality Gifts to Enhance Employees’ Workspaces

“Whether a company is giving…a gift or company swag…the most important thing is to ensure it is something the employee will use,” Thompson says. 

In fact, she recommends giving items that can be used in the office by returning and new employees. Recommendations include portfolio cases, mugs and other office supplies. 

No matter what you give, Thompson says, gifts should be made to last — instead of falling apart or being thrown away. 

3. Give Experiences, Not Just Physical Items 

Thompson suggests throwing an office-wide event. These gatherings both show appreciation and offer an opportunity for coworkers to get reacquainted.

“A reward, like a company lunch or dinner where people can be recognized while spending time with their team, is another good option,” she says.

Rishona Myers, owner of the olive oil retailer Olive Lucy, recommends food tastings and cooking classes for teams. However, “if you’re doing a [food-related] experience,” she notes, “find out if any [guests] have food restrictions, allergies or intolerances.”

She also suggests looking for companies that can host events virtually, especially during the COVID-19 pandemic. 

“It…can bring members of your team from around the country…together for a fun experience,” Myers says. She also notes that such distanced events may require more planning, as materials often have to be sent to participants in advance.

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4. Set a Standard Price for All Gifts 

Whether they are personalized or given en masse, gifts should have the same value for every employee. 

“For example, if I gave one of my subordinates a $20 gift and gave another a $100 [gift], it might be perceived as favoritism,” explains Dr. Nola Veazie, CEO of V-Solutions Consulting, a training and staff development organization dedicated to supporting veterans. “Some might also perceive that I will give that subordinate better opportunities for advancement or be more lenient when there is a need for correction.”

Additionally, executives should keep in mind that, according to the IRS, no more than $25 can be deducted from a gift come tax season. Many companies have a limit on the value of corporate gifts. Executives should ensure gift values align with larger company policies. 

5. Look Beyond the Holidays for Other Opportune Gifting Moments 

If gifts are given only around the holiday season, employees may not see them as rewards for loyalty or hard work and may simply come to expect them. Strategically, giving gifts at key moments can demonstrate additional thoughtfulness and build rapport between senior leaders and employees.

“Corporate gifting can be done anytime,” Myers observes, suggesting gifts be given to mark career milestones, celebrate birthdays or show gratitude.

Have you received a memorable gift from a mentor or supervisor? Share your experience below or in Senior Executive Media’s Leadership Think Tank.

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