Someone sending a Christmas letter

Generating Leads with Seasonal Check-In Messages

Seasonal check-in messages are a subtle and effective way to remind your contacts of your services and encourage referrals. This guide walks you through crafting personalized messages or emails tailored to holidays or special seasons. We’ll cover the strategy, the importance of personalization, and provide a template. Plus, we’ll outline the time estimate, materials needed, and essential tools to make this approach work for you.

Tools & Skills Needed

  • Creativity: For crafting engaging and personalized messages.

  • Attention to Detail: To ensure each message feels personal and relevant.

  • Organizational Skills: For managing your contact list and follow-ups effectively.


  • Email Service or Messaging Platform: To send out your messages.

  • Contact List: Updated and segmented by relationship or interest.

  • Personalized Message Templates: Tailored to different holidays or seasons.

  • Follow-up Plan: To track responses and manage referrals.


The Power of Seasonal Check-In Messages

Seasonal check-in messages capitalize on the goodwill and festive spirit of holidays and special seasons. They serve as a gentle nudge to your contacts, reminding them of your services in a context that feels personal and relevant. The key is to strike the right balance between a friendly check-in and a professional reminder of your services.

  • Step 1: Personalization is Key

    Start with a personal greeting that mentions the specific holiday or season. A message that feels personalized will be more warmly received and less likely to be dismissed as spam.

  • Step 2: Keep It Light and Friendly

    The core of your message should be a friendly check-in. Ask how they’re doing and express genuine interest in their holiday plans or seasonal activities.

  • Step 3: Gently Remind Them of Your Services

    After the personal touch, briefly remind them of your services. It’s crucial to keep this subtle—think of it as a soft sell. Mention how your services could benefit them or someone they know, especially in the context of the season.

  • Step 4: Encourage Referrals

    Politely ask if they know anyone who might benefit from your services. Make it easy for them to refer others to you by offering to provide more information or a quick consultation.

  • Step 5: Express Gratitude

    Always end your message with thanks. Acknowledge their support and express appreciation for any referrals they might send your way.

Template for a Seasonal Check-In Message

Subject: Happy [Holiday/Season], [Contact‘s Name]!
Hi [Contact‘s Name],
I hope this message finds you well and that you‘re enjoying the [holiday/season] spirit. How have you been? Do you have any special plans for [holiday/season]?
I‘ve been keeping busy with [a brief update about your work or life], and I thought of you because [personalized reason related to your services].
As we [celebrate this holiday/enter this season], I wanted to gently remind you of my [services/products] and how they might benefit you or someone you know. If anyone comes to mind, I‘d love an introduction or feel free to pass along my details.
Thank you so much for your continued support. Wishing you a wonderful [holiday/season] filled with joy and peace.
Best regards,
[Your Name]

Sending seasonal check-in messages is a thoughtful and effective strategy for generating leads and encouraging referrals. By personalizing your messages and aligning them with the festive mood of holidays or special seasons, you create opportunities to remind your contacts of your services in a way that’s engaging and heartfelt.