5 Creative Ways Your Sales Reps Can Connect with Clients and Prospects This Holiday Season

Written by: Will Brooks
5 Creative Ways Your Sales Reps Can Connect with Clients and Prospects This Holiday Season

The holiday season can be a challenging time to connect with clients and prospects. While everyone is busy with family and wrapping up year-end activities, they’re also buried in automated holiday greetings.

Skip the mundane, and teach your salespeople these five creative ways to wow their important contacts.

1. Hand Written Holiday Cards

During the holiday season, clients and prospects are bombarded with generic “Happy Holidays!” greetings. Help your salespeople make a list of high value prospects and clients to target with personalized, hand-written holiday cards that will stand out from the crowd.

Keep the messages short and heart-felt, by including small personal messages that may mention, for instance:

  • The contact’s spouse and/or children
  • An activity the salesperson and contact both enjoy
  • A pet or hobby
  • A big win from the year

If the salesperson knows which specific holidays the contact celebrates, they can use holiday-specific greetings, as well.

2. A Genuine Thank You

Help each salesperson develop a short list of important clients, and craft a personal thank you note for each. A great thank you is specific and detailed and may mention times when the client:

  • Inspired or motivated
  • Went above and beyond
  • Advocated on behalf of your organization

Like holiday cards, thank you notes should be hand-written in order to make the greatest impact. If your budget allows, a small gift goes a long way.

3. Offer to be the Designated Driver

Help your salespeople identify upcoming holiday parties that prospects and clients may also attend. Then, have them offer their services as the designated driver for each of those contacts. This gives the salesperson extra positive face time.

As a bonus, if your salespeople aren’t drinking, they’re more likely to make the best impression and represent your organization professionally.

4. Connect with Charity

Are your salespeople involved in charitable endeavors? Make sure this is visible to prospects and clients. Take photos of charitable events, and provide salespeople with newsletters and other collateral they can share with their networks.

For even greater impact, organize events that your salespeople can invite contacts to join. Or consider gifting a donation to a charity in a client’s name.

Toy drives and food drives are popular and easy ways for prospects and clients to contribute and feel a part of your organization’s charitable activities.

5. Extend Hospitality

Encourage salespeople to form closer personal connections with their contacts by inviting them to join them at holiday events and activities.

City tree lighting ceremonies, annual holiday performances, and private holiday parties provide a great opportunity to spend time together and form positive bonds.

Bonus: Get New Year Meetings on the Books Now!

It’s easy to get sidetracked from prospecting and business development during the holiday season, which can make for a slow start to the New Year. Make sure your salespeople are scheduling meetings for January so they can get the New Year off to a great start.

As you finish up the 4th quarter and begin filling next year’s pipeline, make sure your reps have a solid plan to hit their numbers. The Sales Territory Planning Workshop coaches salespeople on the best strategies for developing sales plans that they can implement, track, and measure for success. Your reps will come away from the interactive program with solid, actionable prospecting checklists and a concrete plan for hitting their numbers in the New Year. Learn More.


Keep The Sales Team Focused on What Matters Most with the Sales Territory Planning Workshop


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Written By

Will Brooks

As the CEO of The Brooks Group, Will draws on his leadership, marketing, sales, sales management, and operational experience to help develop and execute the company’s overall growth strategy. Having been in the human capital development industry his entire career, helping organizations reach their full potential through transformational change is a part of Will’s DNA. By putting his name on every single engagement, Will assumes a personal commitment to the success of every client.

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