The shops that win the holiday season aren’t winging it in Q4. They’re already building their offers, reaching out to their best clients, locking in production schedules, and solving problems before they ever show up. That’s what this article is about.
We’re going to walk through how to start selling holiday work today. You’ll get ideas on what to offer, how to market it, and ways to ensure your customers are also thinking ahead. It’s not just about shirts. It’s about giving your clients the kind of help that makes you their go-to partner all year.
You’re the guide. Your customers need someone to lead them through the chaos. You already know what happens if they wait too long. Help them avoid that.
Let’s get ahead of the season before the season gets ahead of you. Here’s what usually happens: Somewhere in November, you realize it’s almost Thanksgiving, panic, and blast out a quick “Still time to order your holiday gear!” post on your socials. You might get a few bites, but it’s mostly chaos. Smaller orders, late approvals, backorders, last-minute art changes, rush fees, and “Can we get these before Christmas Eve?” questions the further you drift into December.
Sound familiar? That’s not a holiday strategy. That’s two lumps of coal in a dirty, tattered stocking. Waiting until Q4 means you’re reacting, not leading. And when you’re reacting, your margins shrink, your quality drops, and your team gets burned out. Even worse? You miss the best work. The better clients have already bought from someone else.
- Tip: If you’ve ever said “I wish this was better…” that’s your cue to fix it now. Q4 started in Q3
The summer months aren’t the off-season. They’re the runway. If you want a strong Q4, treat the dog days of summer as your strategic planning window. This is when you fill your pipeline, prep your offers, and lock in the good stuff.
This is also when clients are open to conversations. They aren’t in full holiday panic yet. They’ve still got budget left. They’re looking for ways to thank employees, impress customers, and finish the year strong. Your job is to lead that conversation. Ask them:
- “Have you thought about doing a branded gift for your team this year?”
- “Want to get ahead of the holiday chaos and reserve your production window now?”
- “Can I show you a few holiday merch ideas that are perfect for you?”
That’s how you guide them. Be the trusted advisor who shows up early and makes the holidays easier.
- Tip: ROI doesn’t mean return on investment. It means return on intent. Your calendar isn’t just a scheduling tool. It’s a selling tool. Block out your November and December production capacity now, and start filling it on purpose.
Contact your best customers first
If one thing is going to make the holiday season easier, it’s knowing exactly who’s locked in early. That means reaching out to your best clients first, getting them on the books, and giving them a reason to commit.
Make a short list of your top 20 or 30 customers. Reach out to them. “We’re prebooking holiday orders now. You always do something great this time of year, and I wanted to make sure you get first dibs on our schedule.” That’s it. You’re not pitching. You’re offering them an advantage. It’s exclusive, it’s proactive, and it shows you’re thinking ahead for them.
If you want to drive action, give them a reason to act. Offer a limited product run. Send them an idea book based on products known to have the best availability. Mock up some examples based on their previous orders in new styles or colorways.
- Tip: Use language like “limited production slots” or “VIP scheduling” to create urgency without being pushy. People value what’s scarce, especially when it saves them stress.
Build the offer now, not later
Customers can’t say yes to something they don’t know about. If you want holiday orders, you need something to show them.
Start by creating a few simple, clear offers. Don’t wait until inspiration hits around Halloween. Don’t overthink it. Think plug-and-play.
Here are a few examples that work great:
- Branded gift kits for employees with a cozy hoodie, a mug with hot chocolate packets, or a cozy blanket. Show how you can use variable data to embellish with their name somewhere.
- Holiday merch bundles for your customers, tailored to their brand guidelines. Demonstrate how long it takes to handle production and ship so their customers receive everything in early December, not in January.
- Client thank-you boxes with embroidered hats, branded snacks, or other custom promo items like Christmas tree ornaments.
- Order early with trust and help build confidence with guaranteed ship dates.
Package the idea with a name, a mockup, and a delivery window. Then put it in front of your best-fit customers and ask, “Want me to reserve one of these for you?”
- Tip: You don’t need 12 options. You need three good ones. Too much choice creates decision fatigue. Keep it simple. Narrow it down to what you think will work best for your top customers.
Lead with what matters to them
The goal isn’t to sell shirts. The goal is to help your clients win the holidays.
Think about what they care about. They want:
- Less stress
- To look good in front of their team or boss
- A smooth gift-giving process
- Something unique that
shows they care
This is where you shift the conversation. Ask what they’re trying to accomplish, not just what they want to buy. You’ll come across as a problem solver, not a vendor.
- Tip: Use phrases like “I thought this might make your life easier” or “A few of our clients did this last year and loved the response.” Make it feel helpful, not pushy.
Make it real with mockups & examples
Visuals sell. A mockup makes an idea real. So, show them something. Use last year’s art and drop it on a new item. Create a version of your idea kit with their logo. Send a short video walk-through of a gift bundle. It doesn’t have to be perfect. It just has to help them imagine it.
Pair that with clear messaging:
- “Book now, ship before Dec. 1.”
- “Lock in your favorite items before inventory runs low.”
- “Preapproved designs mean zero back-and-forth later.”
You’re helping them cross something off their list before they even add it. Let them know that you also offer custom programs, too. “Got something else in mind? Let’s chat! Book a 30-minute call here and let’s discuss!”
- Tip: Your offer is only as good as its clarity. Make it easy to say yes with a short message, one click, and done.
Don’t let the Grinch steal your inventory
If you’ve been burned by out-of-stock items, you know the pain. One minute, your customer is excited about that cozy crewneck in forest green, and the next, it’s gone until January. No fun for them. No margin for you.
This year, it’s even trickier. Between tariffs, freight delays, and limited runs from suppliers, availability can shift fast. You don’t control the supply chain. But you do control how you prepare for it.
Start by narrowing the options.
Choose a few products with strong stock histories and broad color choices. Don’t send your customers to browse the full catalog. That’s a trap. Instead, offer a curated set of holiday-ready picks you’ve vetted in advance.
- Tip: Pick items in multiple colors across sizes so that if one shade sells out, you’ll have a fallback. You might even consider looking at different product manufacturers, so you have some options. Get some product bench strength prepped.
Offer substitutions before they are needed
Speaking of product outages, Plan B shouldn’t happen after a backorder. It should already be in the pitch. When you send your idea kits or mockups, show two versions: your first choice and a solid backup. “If supply gets weird, this alternate color or style still hits the mark.” That kind of prep builds trust. It shows you’re looking out for them.
You’re not just selling product. You’re offering a smooth experience. That’s what people remember.
- Tip: Use the phrase “availability approved” when pitching product bundles. It adds confidence, and shows you’re keeping an eye on stock levels.
Create a sense of urgency without the panic
Your customers aren’t trying to cause delays. They just don’t realize how fast inventory can disappear.
That’s where your role as the trusted guide comes in. Let them know you’re watching the market, and offer clear scheduling windows. “To guarantee delivery by Dec. 12, we need final approval by Oct. 17.” This isn’t a scare tactic. It’s a service. You’re helping them protect their plans and avoid last-minute stress.
- Tip: Include deadlines in your marketing materials. Add a little urgency, such as “Limited slots remaining” or “Early booking ensures delivery.”
Lead gen like a holiday hero
If you want holiday orders in early, you can’t wait until November to start talking about them. The shops that win are already planting seeds in August and September.
This is where your lead gen needs to kick in. Don’t blast out a discount; instead, start conversations. Your goal is to warm up your audience with helpful ideas and early action.
Start simple. Send a short email that says:
“We’re building out holiday projects now. Want to see a few ideas before inventory gets tight?”
That’s it. No sales pitch. Just curiosity and help.
- Tip: Call your campaign something fun. “Christmas in August” or “The Early Elf Program” or “Santa’s Priority List.” You’ll get more opens if the subject line sounds playful, not promotional.
Build a lead magnet that works
A good lead magnet gives your customer a reason to raise their hand. Not everything has to be an order form. Try something more consultative:
- A downloadable holiday merch guide
- A top 10 gift ideas under $25 cheat sheet
- A branded gift checklist for corporate clients
- A holiday timeline planner
to avoid rush fees
The point is to offer value before asking for a sale. Make it feel like a resource, not a brochure.
- Tip: Add a call to action like “Want help picking a few winners for your team?” with a link to book a 15-minute chat.
Go where your customers are already paying attention
Email is great, but don’t stop there. Turn your offers into quick social posts. Drop mockups into LinkedIn, Instagram, or Facebook with captions like: “We’re prebooking holiday production now. This kit was a big hit last year. Want something similar?”
If you have a physical store or shop, build a small holiday preview wall with examples. Mention it to walk-ins or folks picking up their orders. Place a printed, branded flyer on the top of every box before you seal it up.
Keep the conversation going wherever you’re already connecting with clients.
- Tip: Every post, email, or conversation should point to a next step. That might be a link to book a call, a preorder form, or a page with more info. Don’t just show the idea, guide them to act. People don’t know where to go until you tell them.
Be the shop they can count on
Your customers don’t just want a printer or embroiderer. Anyone can do that. They want someone who can take one more thing off their plate. They want a result.
That’s your real opportunity this holiday season. Not just to sell more stuff, but to become the partner they trust to make it all easier. That happens when you lead early, offer smart solutions, and walk them through the process.
Don’t assume they know what to do. Show them.
Put together a timeline. Recommend deadlines. Offer reminders. Help them plan their gifting or holiday promotions before they even realize it’s time.
And don’t forget to follow up. A simple, “Hey, still want to lock in that gift kit before the 15th?” can turn a maybe into a done deal.
People get busy. You staying on top of it makes you look like a pro.
- Tip: Follow-up isn’t pestering. It’s service. You’re helping them follow through on something they already wanted. Not all follow-ups have to be an email, either. If you are like me, you have over 100 unread emails waiting for you right now. Pick up the phone or text them.
Let’s recap: What’s on Santa’s real wish list?
If you want to win the holiday season, do the work now.
- Treat Q3 like your Q4 runway. Start the planning, build your pipeline, and get conversations going.
- Create simple offers and mockups. Make it real, make it visual, and make it easy to say yes.
- Vet your inventory early. Curate products that are available, and prep a backup plan.
- Market with lead gen, not discounts. Start conversations, share helpful tools, and point to clear next steps. Don’t give away your profit to book jobs.
- Be the guide. Show up early, lead the plan, and help your customers avoid the chaos.
This isn’t about pushing product. It’s about being the shop they can count on. Start now, not in October. Santa’s watching. Get on the nice list for a change.
