The Senior Executive’s Holiday Gift Guide - Senior Executive
Teamwork and Team-Building 8 min

The Senior Executive’s Holiday Gift Guide

To help busy executives with the extra demands of the holiday season, we’ve curated a list of good boss gift ideas, from virtual group wine tastings to home office upgrades.

by Kimberly Valentine on November 16, 2022


  • Leaders should appreciate their teams all year round, but the end-of-year holiday season is a good time to show your appreciation with thoughtful gifts.

  • Personalizing your gifts, as well as including a handwritten note, can be more meaningful to the recipients.

  • Team experiences can double as a gift and a bonding opportunity.

Demonstrating understanding and showing appreciation as an executive should be prioritized all year, but the holiday season offers the perfect time to connect and express gratitude through gifting. And if the last couple of years have taught us anything, it’s that humans value human connections — and cultivating those connections in the workplace, whether we’re in person or virtual, is critical. 

“While executive leaders must continue to focus on driving engagement and productivity to achieve business results, they must also demonstrate their ability to understand the employee’s journey to find balance amid continued uncertainty in this ever-changing world,” says Cindy McDaniel, business coach and a chair at Vistage, an executive coaching organization. 

When searching for gifts for employees, take a thoughtful approach to show your team members that you value their commitment to the company. Gifts that feel intentional pack in more meaning than generic boss gifts such as Visa gift cards or popcorn tins. “When executives give a thoughtful, personalized gift, it makes their team feel appreciated, valued, and seen,” says Sarah-Nell Walsh, founder and CEO of Wayfinders Executive Coaching.

So, in your search for the best gift ideas for coworkers this holiday season, consider these top picks to show your gratitude for the talent and hard work each of your team members contribute throughout the year. 

Virtual Team Experiences 

The company-wide holiday party is a great time to get together to celebrate, but for executives who prefer a more intimate gathering with their own team, a virtual experience such as a wine tasting, cooking class, or terrarium workshop provides an opportunity to celebrate the holidays in a stress-free environment. These experiences also offer flexibility for any team’s dynamics, whether members participate from their own homes, together in the office, or a combination of both.

Terrarium Workshop: Take an hour out of the workday to join a virtual class where each of your team members can assemble their own terrarium. Confetti offers a Zoom-based instructor-led experience for up to 300 participants at $79 per person, and the terrarium kit is shipped to participants before the class date. 

Cooking Class: Alternatively, an afternoon can be spent learning to cook a new recipe. The Chef and The Dish offers Zoom-based, 90-minute cooking classes that can accommodate up to 20 attendees, each in their own kitchens. A professional host will walk your team through the preparation of the chosen dish, which can be catered to dietary needs. Plus, grocery coordination is offered at an extra cost so that your employees don’t need to stress over having the right ingredients on hand. The cost of a group cooking experience with The Chef and The Dish starts at $1,000 for 10 devices. 

Hosted Tastings: Virtual or hybrid wine, beer, and cocktail tasting sessions are offered by Priority Wine Pass. You can choose your tasting experience from a selection of wine regions, breweries, and spirits. Themed experiences are also available, such as the holiday wine, chocolate, and cheese kit ($135 per person) and the holiday cheers cocktail tasting ($95 per person). There are also non-alcoholic and food-tasting experiences, such as the Columbian coffee and chocolate tasting ($160 per person) and the around-the-world-cheese tasting ($105 per person). Sessions vary in length, but most are an hour or less, and the kits can be shipped to multiple addresses. Take note of the states each experience can be delivered to, as restrictions vary. 

• Cost: $80-$200 per person 

• Level of personalization: Low 

• Time investment: High

• Can an executive assistant help?: Yes, with coordination, but the executive should participate in the experience. 

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Beverages of Choice

Coffee Subscription: Gifting a wine, liquor, or coffee subscription is another way to appeal to your employees’ tastebuds based on their preferred beverage. For coffee lovers, Verve Coffee Roasters serves up single origin or blend coffee beans; or choose between light and adventurous, classic and approachable, espresso or decaf from The Roasters Pack. Both offer prepaid three-, six-, and 12-month subscription options. 

Wine Subscription: Winc gift card amounts equate to the number of months your employees will receive a four-bottle box filled with their choice in wines ($60 for one month, $100 for two months, $150 for three months). Winc’s assortment of wines includes low-sugar, no-sulfite, sustainable, and vegan options. 

Spirits Subscription: If you know your employees’ preferred choices of liquor, you can opt to have one bottle per month delivered to their homes through Taster’s Club. Three-, six-, and 12-month prepaid membership options are available ($45-$80 per month). Craft Whiskey Club offers prepaid two-box/four-month ($240) and three-box/six-month ($360) options for whiskey aficionados.

Take note of the states the wine and spirits subscriptions can be delivered to, as restrictions vary. 

Crystal Set: To go the extra mile, your employees’ favorite spirit can be paired with the right style of Waterford crystal, Walsh’s top choice for holiday gifts. “I especially like this gift because it communicates investment and longevity,” she says. “It shows that you value this leader; you know them, and you expect them to be on your team for years to come.”

• Cost: $60-$400 per employee

• Level of personalization: High 

• Time investment: Low

• Can an executive assistant help?: Yes

Home Office Upgrade

Indoor Plants: Especially for remote teams, choosing a gift that will make your employees’ home offices a more comfortable space to work is a thoughtful gesture. Consider a gift card from Bloomscape (in amounts of $50, $100, or $200) so your employees can add some greenery to their office by choosing from a variety of indoor plants, sorted based on maintenance level, amount of light, and pet-friendliness. Bloomscape provides plant guides, and there are multiple saucer color and eco-friendly pot options to match their existing office décor.

Ergonomic Furniture: On the spendier side, you can upgrade your employees’ offices with ergonomic furniture from Branch. A $350 gift card covers an ergonomic chair. There are also options of gift card values from $10 to $1,000, so your team members can choose items such as a monitor arm or standing desk to complete their home office.  

• Cost: $10-$1,000 per person

• Level of personalization: Low 

• Time investment: Low

• Can an executive assistant help?: Yes

The Gift of Time 

The gift of time cannot be overlooked this holiday season, especially for teams that have rallied to reach end-of-year goals. Plus, with many employees back in the office, time at home with families is ever-more important as we head toward the end of the year. 

McDaniel recommends giving handwritten cards to express appreciation of each of your team members. “Most importantly, the note should include a wish for them to relax and enjoy some good old-fashioned fun with their family and friends. This may also include offering an additional floating PTO day or day off during the holiday season.” To add an element of fun to this gift idea, she suggests pairing it with a board game and puzzle that your staff members can enjoy with their loved ones during their extra time away from the office. 

• Cost: $20-$60 per employee, not including the day of PTO

• Level of personalization: High

• Time investment: Medium 

• Can an executive assistant help?: Yes, but cards should be handwritten by the executive. 

Gifts That Keep Giving

Charity gifting is a wonderful way to lean into the holiday spirit, and there are opportunities to engage your employees in the experience by enabling them to choose who and what the gift will support. A Kiva Card, for example, allows recipients to choose a business they want to invest in — locally or internationally — through a Kiva loan. These microloans help underserved entrepreneurs gain the resources they need to get their businesses off the ground. Once the loan is repaid, your employee can reinvest it into a new business. Kiva Cards start at $25 and are available in varying increments up to $2,000.

Gifting a TisBest gift card enables recipients to choose the charity they want to donate to. You can opt for printed, digital, or physical gift cards and upload an image to use on the front of the card, such as your company’s logo. Unlike some charity gift cards that deduct a percentage of the amount for administrative expenses, the full amount goes to the charity and there is an optional nominal service fee added at the time of payment. For those looking for gift-giving that can be tax-deducted, this is the way to go. TisBest offers gift card amounts of $50, $75, $100, and $200, or a custom amount can be chosen.

• Cost: $25+ per person

• Level of personalization: Low 

• Time investment: Low

• Can an executive assistant help?: Yes

Curated Gift Boxes

While corporate gift boxes may seem a bit generic, there are ways to add greater personalization for your individual team members. Something Splendid and BOXFOX are among companies that allow you to choose the items you want in each box. While this option might not make sense for a larger team, as it does require extra time to decide how to build each of your employee’s gift boxes, this level of personalization can show your thoughtfulness. Plus, if your executive assistant has a good idea of what your employees prefer, they’ll be able to better assist in the gift-ordering process. Complete the personalization of this gift idea by including a handwritten holiday card. 

• Cost: Varies based on the items each box contains, but plan for $80-$200 per person

• Level of personalization: High

• Time investment: Medium

• Can an executive assistant help?: Yes

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