The holiday season can bring some of the biggest sales days of the year. That also makes it tempting to squeeze in one more website update before the rush begins.
Maybe there is a new extension you want to install. Maybe your team has an idea for improving the checkout process. Or maybe a developer recommends a change that seems small enough to make at the last minute.
But before you approve any holiday development work, it is important to understand what is actually at risk.
One extension, even one that costs only $99, can potentially affect your entire checkout experience. The problem is that many store owners do not know which extensions and customizations are sitting directly on the path between a customer deciding to buy and completing their order.
Before approving another change, ask your developer these three questions.
1. What Actually Touches Checkout?
When a developer tells you that your store is ready, that sounds reassuring. But “ready” does not tell you much if they cannot explain exactly what is involved in your checkout process.
Before you can assess the risk of a change, you need a complete picture of every extension and customization involved in the ordering process.
Ask for a list of anything that touches:
- Checkout
- Payment processing
- Shipping
- Taxes
- Discounts and promotions
- Loyalty and reward programs
- Inventory
- Order processing
- Any custom functionality that changes the cart or checkout flow
The total number of extensions on your website is not necessarily the problem. A store could have dozens of extensions, and most of them may never affect an order.
What matters is knowing which ones are sitting on the money path.
Once you have the list, ask what each extension does, whether it is still actively maintained, when it was last updated, whether it is compatible with your current platform version, and whether custom code is overriding it.
If your developer cannot answer those questions about a specific extension, that is useful information. It may not mean the extension is broken, but it does mean you have identified something that deserves a closer look.
2. Where Are the Biggest Risks?
The next question helps you understand whether your developer sees the bigger picture.
A developer can know how to install an extension. But an experienced e-commerce developer should also understand what that extension can affect across your entire business.
As you head into the holiday season, three categories deserve extra attention.
Anything That Touches Payment or Checkout
This includes payment gateways, checkout replacements, subscriptions, financing tools, fraud detection, and digital wallets.
If one of these tools fails, customers may not be able to complete their purchase. And during a major sales event, even a short disruption can matter.
Anything That Calculates Information in Real Time
Shipping rates, tax calculations, inventory availability, promotions, and loyalty rewards often rely on external APIs and services.
That means your website itself could be working while another service it depends on is slow or unavailable.
Anything Old, Heavily Customized, or Poorly Maintained
An extension that has not been updated in a long time can create risk. So can custom code written years ago that nobody currently on the team fully understands.
It is also important to remember that an extension being updated does not automatically mean it is safe. It could still conflict with something specific to your store.
The goal is not to hear a general reassurance that everything should be fine. You want your developer to identify specific risks and explain how they are being managed.
3. How Did You Test It?
“We tested it” is not a complete answer.
The more important question is how your team tested it.
Before approving a holiday website change, ask whether they tested different parts of the complete customer journey, including:
- Guest and logged-in checkout
- Mobile checkout
- Different payment methods
- Different shipping methods
- Coupons and promotions working at the same time
- Tax calculations
- Higher order volumes
- Different product combinations
- Integrations connected to the order
- What happens if an outside service is slow or unavailable
This list is not meant to overwhelm you. It is meant to help you understand whether your development team has thought through the full checkout experience or simply clicked through it once and called it done.
And there is one more question you should always ask:
Do we have a rollback plan if something breaks?
A strong answer should be specific. Your developer should be able to explain what touches checkout, what risks they identified, how they tested the changes, and what the process is for rolling back if something goes wrong.
“I think everything is updated” or “We never had a problem before” are not the same as having a real plan. And “It should be fine” is not a strategy when your holiday revenue is on the line.
Bonus Question: What Should Wait?
There is one more question that can tell you a lot about your development partner:
What are you recommending we do not touch during the holiday season?
As you get closer to your busiest sales period, the risk-reward calculation changes.
A critical security update or bug fix may need to happen. But installing a brand-new checkout extension just days before a major sale is a very different decision.
Black Friday and the holiday rush are not the time to make website changes simply because you can. They are the time to protect the revenue machine you have already built.
In fact, a developer who recommends waiting until January for a nonessential change may be showing more expertise than one who is willing to keep changing things without considering the risk.
If your developer has a clear, thoughtful answer about what should wait, that is a good sign they understand what is at stake.
Protect Your Store Before the Holiday Rush
You do not need to become a developer to ask better questions about your website.
These three questions can help you look beyond general reassurance and understand what is really happening behind the scenes:
- What actually touches checkout?
- Where are the biggest risks?
- How did you test it?
And before approving any new development work, do not forget to ask what can wait.
Black Friday is not the day to discover a weakness that could have been identified weeks earlier. The more you understand about the risks before the holiday rush begins, the better positioned you will be to protect your store and your sales.
Prefer to Watch Instead?
If you’d rather watch than read, check out the full YouTube video, 3 Questions to Ask Before Any Holiday Dev Work.
In the video, I walk through the questions you should ask your developer before approving last-minute changes and explain what to listen for in their answers. You’ll also learn why knowing what not to change can be just as important as knowing what to fix before the holiday rush.
