Yes, the leaves are still on the trees but it’s time start thinking about getting your online store ready for the holidays. For many artists and makers selling their goods online, the winter holiday season is the busiest and most stressful time of year. Busy is great, but stressful isn’t. Here are some ways to make this year’s holiday season your most successful and your least stressful one yet.

Step 1: Getting Your Customers Ready for the Holidays

Your customers are just as swamped at the holidays as you are, so they need help too.

The single biggest thing you can do to reduce your stress and to give your and your customers happy holidays is to set clear expectations and communicate everything as clearly as possible.

Your customers are just as swamped at the holidays as everyone else, so they need help too. Here are a few things you can do to make sure they don’t set themselves up for disappointment:

Start sending reminders about holiday ordering early

Maybe even sooner than early November, if you have long-lead-time items. Use these emails to promote new products, holiday specials, and any discounts you’re running.

When is the last day you’ll guarantee delivery by Christmas?

Make sure to leave yourself some wiggle room just in case. Put that date everywhere. On a banner on your website. In every email you send. On every product page. On packing slips for other orders. Make it as hard for your customers to miss as you possibly can.

Check Your Policies

What are your policies for returns? Refunds? What happens if the FedEx truck gets run over by a reindeer and your packages get delayed, damaged, or destroyed? Having well thought out, well documented policies takes some of the stress out of handling the unexpected, and it gives you something to point to if you have the misfortune of dealing with a rabidly unreasonable customer.

Update your Order Status Emails

When it comes to giving customers the latest updates on their orders, there’s no such thing as too much communication. Especially if that order is a gift for dear old Grandma.

Woocommerce has a pretty comprehensive set of customer emails out-of-the-box, but there are two I recommend adding: a shipment notification email with the tracking number, and a follow-up email a day or two after the order is scheduled to be delivered making sure that everything went amazingly.

What happens if the FedEx truck gets run over by a reindeer and your packages get delayed, damaged, or destroyed?

If you’re not in to sending these emails manually, a fantastic way of adding these emails to your workflow is with Shipstation. Shipstation has detailed and well-designed shipment notification emails with tracking, and it integrates with MailChimp (which you’re using for your email list…right?) to allow for automated follow-up emails.

Step 2: Getting Your Online Store Ready for the Holidays

Think back to last year’s holiday rush. What worked and what didn’t? Which products kept you up all night struggling to keep pace with demand? What parts of your ordering, packing, and shipping process became time-consuming, ulcer-inducing bottlenecks?

If this is your first holiday season, look back over the past few months and ask yourself the same questions. What’s been the weak link in your process, the things that take up way more time than they should?

The things that gave you trouble before will just keep giving you trouble this year if you don’t do something about them.

Is there a particular product that sells well but takes so long to make that you’ll be pulling all-nighters from now until Groundhog Day to meet holiday demand? Don’t make so many!

The things that gave you trouble before will just keep giving you trouble this year if you don’t do something about them.

I know, that sounds absolutely insane. Well, think about how many times you’ve heard products advertised as being “limited edition”. Usually this means absolutely nothing. But what if you make a limited number of your time-consuming product with a unique difference, especially for this year’s holiday season?

You will save yourself time, and you will almost certainly sell out even if you add a little bit to the price. Customers are attracted to the unique or one-of-a-kind, especially if there’s only one chance ever to get one.

If this seems a little gimmicky to you, don’t do the whole special-edition thing but still limit how many of these products you have. Just remember what I said about communication: make sure people know that there is a finite quantity available, and that if they wait until the last minute there just might not be any more left. You’ll make your sales sooner and avoid angry would-be buyers.

OK, time to get back to Shipstation. Are you still processing orders manually, logging in to your USPS, FedEx, or UPS account and printing labels one at a time? This year is probably the time to stop. Shipstation takes care of printing packing lists and labels automatically, and can use regular office printers and thermal label printers. As of this writing you can sign up for Shipstation for $9 a month if you process under 50 orders a month, $25 for 500, all the way up to $145 a month for unlimited orders. And of course, Shipstation integrates with Woocommerce seamlessly.

Now you can print out a stack of packing lists and labels, hand them off to your assistant, and be done with fulfillment!

Wait, what was that? You don’t have an assistant?

Step 3: Getting Help for the Holidays

I’m not referring to the therapist you’ll need come January. I’m talking about temporary contract employees to help with your most time-consuming tasks, like packing and shipping or responding to customer emails.

Where do you find your own private Christmas Elves? If you’re in an area with an active maker and handmade community, ask around. There are bound to be names that come up, and those are usually your best bet as long as someone else hasn’t snatched those star performers up already.

Next come sources like Craigslist or HireMyMom. Craigslist, being local, is good for any type of help, whereas HireMyMom is better for virtual assistant type work.

When it comes to picking the right people, an in-person interview, preferably on-site, is a must. One of my favorite interview tricks (which I can hardly claim as my own) is to ask your interviewee for a couple of ways they would improve your operations.

Use help from friends and family with care if you want to preserve your relationships into the New Year.

If you’re lucky like we are in Denver, you might have an organization like the Mile High Workshop that, in their words employs people rebuilding their lives after being in jail or prison, recovering from addiction, or transitioning out of homelessness. Mile High Workshop offers everything from fabrication to assembly to packaging & fulfillment.

Finally, there are families and friends. Use these resources with care if you want to preserve your relationships beyond December 31st! The following guidelines for hiring help apply double when things get personal:

Set clear expectations

How many days a week? How many hours a day? Start and end times? What to do if you can’t make your shift? When’s pay day, and how much do you pay?

Set clear responsibilities

What is considered “part of the job” and what isn’t?

Set clear boundaries

Again, this applies double if you’re hiring friends and family. Strange though it may seem, your business is, well, a business, and you (the boss!) get to decide what a professional environment means to you.

Set everyone up for success

No matter how simple the task seems to you, remember that you’ve done it hundreds of times and the people you hire may have never done it in their lives. Take the time to walk through every step of the job to be done and make sure there are no unanswered questions at the end. The last thing you need to be doing is unpacking and re-packing orders to fix a tiny but crucial detail.

Let them do their job

Once you have your helpers trained and set up, be available for questions, but otherwise let them be. You hired them so you didn’t have to do this stuff, right? So no micro-managing. If you hired well and trained well, everything will be fine.

Step 4: Ready, Set, Ship!

Every holiday season is different. Sometimes Santa brings you everything on your list, and sometimes the Grinch does his best to push every ounce of Christmas Cheer out of your heart. For a rapidly growing shop selling online each year can seem like starting over. Maybe you’re not ready to try all of the tips in this article, but hopefully there are some bits in here that will make your holiday season go a little smoother.

Now get out there and enjoy those last few days of summer and try to pretend you don’t hear the distant sound of sleigh bells approaching!