How to Communicate with Customers This Holiday Season

By Baillee Perkins
Oct 21, 2022
Learn how to best communicate with your customers this holiday season!

Supply chain issues are impacting product availability while inflation is raising the cost of everything imaginable. This means your holiday shipping season might not run as smoothly as it has in the past. So, communication will be key! Being transparent with your customers about how their orders are shipped, carrier delays, shipping deadlines, and all the other parts of your shipping process needs to be a big focus for your small business. To help you create the best communication for your customers, we’ve created this handy guide to give you some ideas. 🧠

Image source: The Grove

Table of Contents

  1. Placing an order
  2. Picking a service
  3. Creating a shipping label
  4. Choosing the right packaging
  5. Shipping a package
  6. Tracking a shipment
  7. What are holiday shipping deadlines?
  8. How does ShippingEasy help my small business ship my orders?
  9. Conclusion

Placing an order

Once a customer places an order it’s easy to forget everything a small business does to get an order out. And, let’s not forget all the work that goes into having your customers visit and purchase from your store in the first place. Offering free shipping or free shipping over a certain threshold does impact your business’s profits, and creating email campaigns to give your customers promo codes and discounts takes time out of your schedule that could be focused elsewhere. 

Giving a brief overview of your business to your customers is the first step in giving them a peek behind the scenes. Show your customers how your business started, and how your business operates. Spotlight your different team members. Connect with your customers by sharing your business’s mission and the obstacles your business has overcome. Our user, Ice Shaker, is starting a series on Instagram for their fifth anniversary of being on Shark Tank where they show customers how their product has evolved since they started. 

Read more about how Ice Shaker uses ShippingEasy in our case study!

You could also make a video on social media where you show your customers how you create your email campaigns. You could even put a fun and creative spin on it by making a behind-the-scenes documentary or following social media trends. ShippingEasy user, Furls Fiberarts, hosts live streams on YouTube, and we’ve included one below where they talk about the business in-depth. 

Video Source: Furls Fiberarts
Learn more about Furls Fiberarts in our case study.

Picking a service

As we mentioned before, it’s easy for your customers to not think about all of the decisions that are made and all of the details that are carefully planned to get their packages delivered. We know you have to make decisions like which carriers/carrier services to offer your customers by comparing shipping rates as your orders sync into ShippingEasy. But, your customers probably don’t. You don’t have to show your customers each and every single step of the process, but you can still be transparent. 

Instead of showing your customers how you choose each and every single service you offer, show them the benefits of the carrier services you do offer. For example, Priority MailⓇ comes with tracking information, so they can follow their package in transit. You can also highlight Priority Mail ExpressⓇ being a guaranteed service from USPS, so if your customer doesn’t receive their package in the delivery window, you can submit a request to USPS to see if you’re eligible for a refund. Showing your customers all of the benefits of the carrier services you offer helps them to better understand why you made certain decisions, and they’ll appreciate the honesty. ShippingEasy user Pet Costume Center does a wonderful job of outlining exactly how selected services work for their customers.
Image source: Pet Costume Center 
Find out more about Pet Costume Center with our case study!

Creating a shipping label

Orders sync into ShippingEasy → Confirming customer addresses → Creating a label → Buying a label → Printing a label on your thermal printer with ConnectEasy 

This flow chart is confusing to those who don’t know about shipping. However, it’s possible to break it down for your customers to understand. Think back to high school or college. When you had to write an essay, you’d get your assignment, confirm you understood what was being asked, write your paper, read through your paper for any mistakes, print your paper, and deliver it to your teacher/professor. Another great analogy is to think of creating your label like a recipe. You find what you’d like to cook, confirm and buy the ingredients, mix everything together, bake it, and deliver your new dish straight to your tastebuds. 

Using comparisons your customers will understand is the biggest tip we can give you. It’s all about knowing your audience, and connecting with them in ways they’ll understand. Take this blog. If you came to the ShippingEasy blog, and we were talking about juggling, you’d be confused, right? Think of your customer communications in the same way. Your customers are coming to you and are expecting to hear about your business, your products, and your process. 

Keeping with the recipe analogy, check out How to Ship Baked Goods!

Choosing the right packaging

Unwrapping the mysteries of your packaging is another area you can use to connect with your customers. Explain why you use the specific packaging you do. Let your customers know you use sustainable packaging. Don’t be afraid to brag about your brand for helping the environment! 

Learn more about our Greenest Way to Ship Program in our blog.

Also, if certain items require special packaging, talk about it. Tell your customers if a carrier service has packaging guidelines, so you can only use carrier-specific packaging. This way, your customers aren’t left wondering why different orders come in different packaging. You can even send them some of our How To blogs to illustrate how much goes into packaging specialty items. We promise we don’t mind. ShippingEasy user Soapie Shoppe has an Instagram post where they show how their wholesale bath bombs arrive, so customers can know exactly what to expect that we’ve included below. 

For more information on the Soapie Shoppe, read our case study.

Shipping a package

We’ve finally reached the main attraction: shipping a package. Your customers eagerly await their shipping confirmation email, letting them know their package has shipped. Little do they know, before their email, you have to either schedule a pickup or drop off your shipments with your carrier. This is another great opportunity for you to give your customers a behind-the-scenes peek at how your small business operates. ShippingEasy user Cornucopia Popcorn posted a picture of their shipments on Instagram with one of their employees to show their customers how much they appreciate them and that their orders are being shipped. 

You can find more ideas on explaining shipping to your customers in How to Ship a Package!

Tracking a shipment

Providing tracking is one of the easiest ways to communicate with your customers. Tracking numbers are included in your shipping confirmation emails and Branded Tracking emails for eligible shipments, so those numbers are readily available to your customers. But, you can go the extra mile by informing your customers of any potential carrier delays due to COVID and/or the higher holiday shipping volume. USPS also keeps an updated list of their international shipping restrictions, so you can keep your customers informed. 

Create the perfect holiday email to keep your customers coming back with the help of our blog.

What are holiday shipping deadlines?

Holiday shipping deadlines are dates issued by carriers. These dates are the last possible dates a package can be sent and still get there for the holidays. For example, a carrier service might need packages to be sent by December 16 to get to their destination by Christmas because of the high shipping volume during the holiday season. Giving your customers an idea of the holiday shipping deadlines ASAP will help them to plan their gift buying, and they’ll appreciate it. 

You can check out domestic shipping deadlines over on our blog!

How does ShippingEasy help small businesses ship my orders?

We’ve talked a lot about how to communicate with your customers, but this section is for you! Whether you’re a new ShippingEasy user, or you’ve been with us for years, we want to highlight a couple of features for you to utilize this holiday season: Shipping Rules and saving a custom package

Did you know that you can actually save your most-used packaging options in ShippingEasy? Then, you can take your package options, include them in your shipping presets, and use shipping presets in your Shipping Rules. Those Shipping Rules can be used to assign presets to certain orders, assign orders to specific users on your account, and/or assign packing slip templates to orders. This way, we’re helping you help your customers by creating a smoother shipping process for you and your team. 

Trim your tree and shipping costs with a 30-day free trial of ShippingEasy.


With all of the craziness the holiday season brings in, your customer may not know all of the work that goes into getting their orders out. Each shipment has to be packaged, needs a label created and printed, and has to be picked up or dropped off ⸺ and not including carrier delays, supply chain issues, and other obstacles. Keeping your customers in the loop not only helps them track their orders but shows them how much you value their business. Sleigh the obstacles that may arise this holiday season by being as transparent as possible about your shipping process, and remember the few tricks you have up your sleeve with ShippingEasy. 

Make holiday Shipping Easy with a 30-day free trial!
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Baillee Perkins

Baillee Perkins is a writer of shipping by day and pop culture by night, so her Google search history is an actual nightmare.

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