9 Biggest Email & SMS Mistakes to Avoid For Black Friday Cyber Monday 2023

The 9 most common mistakes for ecommerce marketers & email marketers to avoid leading up to and during Black Friday/ Cyber Monday. And strategies for how to avoid each and make the most of your holiday marketing!

Robbie Fitzwater
Updated on

For eCommerce marketers and business owners, the buildup to the holiday season can be somewhat intimidating. So much of this planning falls squarely on the email marketer, who is responsible for building anticipation, building a list, and converting it when it matters most. Follow along for the 9 Biggest Email & SMS Mistakes to Avoid For Black Friday Cyber Monday 2023.

The strategy needed for e-commerce email marketers and businesses in this window is completely different than the strategy for the rest of the year.

Things can get a bit chaotic, and everyone is focused on maximizing their email marketing this season. And with the clock ticking until the holidays, there is no better time to start planning than now.



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Black Friday

We’ve seen plenty of mistakes leading up to and during Black Friday/Cyber Monday, so we wanted to help you avoid them!

We laid out some of the most common holiday mistakes we see made in holiday email marketing strategy so that you may avoid them and give you a smooth roadmap to follow!

What we’ll cover:

  1. 9 Biggest Holiday Email Marketing Mistakes to Avoid in 2022
    1. Not Planning Early Enough
    2. Playing It Safe And Failing To Stand Out
    3. Not Adjusting Creativity
    4. Not Varying Messaging/Offers/Experience
    5. Not Optimizing Calendar
    6. Treating Everyone The Same
    7. Not Training Their Audiences
    8. Not Aligning With Other Marketing
    9. Freaking Out On November 10th
  2. Conclusion 

1. Not planning early enough 

In email marketing, it is essential that you start planning early so you can carry out your ideas smoothly and efficiently when the day arrives! 

I’d recommend that you start planning around your holiday marketing calendar in mid-August or early-September

The best strategy starts with reviewing what has and hasn’t worked in the last few years and what you can leverage this year. 

It would be best to start planning your goals and requirements for fulfilling those goals. So that once your buildup for the holiday season begins in late October or early November, you have the majority of your assets ready to go. You get to focus on being proactive in your efforts instead of being reactive to what you need to do.

Suddenly, you are pressing play on the content, campaigns, messaging, and creative you had worked on during previous months.

The earlier you start with your planning phase, the less you will be scrambling between ideas and catching up with the plans you have in mind. That will allow you to maximize and effectively use all the opportunities presented to you during that time.

So start planning, brainstorming, looking for ideas, and start taking suggestions from your creative team so you can bring them to life and you’re not burdened when the time comes to apply them.

2. Playing it safe and failing to stand out 

Sometimes, playing it safe might put you in danger! 

Typically, this is the time of the year when you have to go a little farther to the edges than usual so you can differentiate yourself and stand out in the industry. 

  • Zig when others are zagging 

This is where you need to ask yourselves questions like, “Hey, how do I Zig when everybody else is zagging. Because this is the hardest time to stand out. Your motto for the holidays should be “different is better than best.”

  • Send more

One of the most common mistakes marketers make is holding themselves back while sending emails, such as sending one email on Black Friday and Cyber Monday. One email a day makes sense the rest of the year, but the same rules do not apply here. 

They don’t realize that everybody’s inbox is so inundated with so much content during those days that one email from your company might get buried somewhere under the pile of other emails they are receiving those days. You must get out of your comfort zone and send more of your content in different emails so that there is a significant possibility of them reaching the audience.

We recommend three emails spread out during the day on Black Friday and Cyber Monday and two emails a day on Saturday and Sunday in between.

  • Best-performing subject lines

You may also get your customer’s attention by using your best-performing subject lines. For example, the subject lines that have given you more open rates previously and using them again might be of great benefit. You may also have some fun using emojis in the email content’s subject lines, making the email more eye-catching, attention-grabbing, and engaging.

This is the time of year to play the hits!

  • Borrow ideas

To be more innovative, you can borrow ideas from other industries, use them, and modify them according to your requirements. These ideas, as taken from outside, would be something new in your industry and will let you stand out against other brands and businesses in the industry. 

But what’s important is to align what you borrowed from other industries and make them your own.

For example, you can borrow ideas from other industries regarding how you will be driving shopping-related content on Black Friday, Cyber Monday, or the shopping holidays.

Like, are you going to do a live shopping feed on Instagram? That’s something you can distribute and share through email.

Look at what women’s cosmetics brands are doing. So many are crushing it in terms of innovation!

  • Communicate Early

To stand out in your industry, you must make sure your offers are unique and something that you or anyone in the industry has never offered. That is one thing that will attract your audience, but there is something else. 

Whatever you plan to offer in these holiday seasons, you must communicate it to your audience early. Build hype regarding these offers and get your audience to engage through emails. Even if you’re not giving any offers, communicate that early, too.

Ensure that people know that early so they’re not thrown off by assuming everyone has offers on Black Fridays and Cyber Mondays. In this way, you can also hopefully level out sales throughout the month to not be overwhelmed by a surge of orders.

  • Limited time offers 

You can also offer limited-time products as they are a unique concept too. In this, you offer something only available in a scarce time window and let that scarcity drive action. 

People tend to get the exact offers repeatedly during the holiday season; scarcity and limited-time offers play a vital role in bringing the audience to your brand by interrupting the pattern they are getting.

3. Not adjusting creative

Using the same branding in the holiday season as you do throughout the year can be a put-off for your audience. So it is advised that you vary things a little bit. 

Just like during the holiday season, you see brick-and-mortar stores decorated for the holidays; in the e-commerce world, you can do that by varying and adjusting the creativity in your emails.

For example, you can jazz things up by changing the header of your emails and adding some holiday touches to them, or you can also change the popover designs for holidays only. 

Black Friday Cyber Monday content email with header change

You can do that in the universal content template in Klaviyo. It would be a great place to do that because you can also adjust the creativity inside your automation.

So, if your header is consistent across all those universal blocks, you can adjust that programmatically in your universal title and change it across the board. And that’s quite a unique way to customize some of your automation.

Doing all these things is a small deal, but it goes a long way in getting people in that mindset of shopping during the holidays.

Think of it as priming your audience to spend more money!

Another thing that is yet again important here is the message’s relevancy. Ensuring you are sending the right messages to the right audience, a statement that aligns with their requirement, is crucial. 

You can also include countdown timers. However, make sure to do just what is necessary, but it would be effective to incorporate one or two of them as they might also work as reminders for the audience and urge them to take action before the offer expires. 

Black Friday Cyber Monday email with countdown timer

You may also include a callout to the sales and the promotions you will do on Black Friday and Cyber Monday in your automation. As we mentioned, these can be done more effectively on the universal content template in Klaviyo. 

4. Not varying messaging/offers/experience

Not varying means doing the same thing repeatedly and not making things special and unique. Something a good marketer needs to avoid is sharing the same message over and over in their Black Friday email marketing. 

  • Play the hits and recycle content 

The question is how to avoid that, and how do we lead into that Black Friday and Cyber Monday holiday? The answer is ‘always put your best foot forward and play the hits first.’ It means if some of your emails and content have performed well for you in the past during the year, recycle that in this holiday season and share that engaging content. It’s an easy way to get people excited and engaged in your offering.

  • Design popovers

During holiday sales, you can also design popovers for your websites to lead the viewers straight to the sales. This would be a quick method for them to see what items are on sale and an easy way to get them active and engaged, especially if they are existing purchasers.

  • Create a holiday collection

Speaking of existing purchasers or regular customers, you may want to offer unique products to them this holiday season. You can offer them something unique and create a holiday collection for those best offers. This is just like the hanging fruit technique, like sending them an array of products that are easy for them to purchase around specific holidays.

  • Open up your list

You may decide to open up your list at this time of the year. 

There could be a group of unengaged people on your list who might be unengaged purchasers and non-purchasers. You don’t want to do it too often, maybe at the beginning and end of your biggest holiday promotions.

Need help building an email list? Check out our ultimate guide here.

I always joke that going too far back into the unengaged segment of your email list is
like trying to find your potential partner in a bar.

The closer it gets to the last call, the less likely you will find someone you want to bring home to your parents.

Yes, it can and does happen, but it is the exception, not the rule.

Trying it once in a while can be fine, but making a habit of it can be problematic… (you can fill this one in for yourself 🤕)

It is also more effective to send plain text emails to ensure strong deliverability and make that call to action simple and straightforward. However, going too deep into that list can be a dead-end experience. 

  • Adjust the trigger flow

Adjusting your trigger flows’ timing could be another crucial holiday email marketing strategy. Suppose your ideal time for an abandoned cart trigger is three hours after checkout starts; you should make it 1 or 2 hours during the holidays so that the audience takes action sooner.  

It is okay to be aggressive with emailing in times like these because people are engaged in many other things. There might be a lot of different brands fighting for their attention. So if you adjust that trigger, you hopefully can bring them back in while they’re still in that same shopping journey and hopefully can pull them through.

5. Not optimizing calendar

One of the most common mistakes e-commerce businesses make is not optimizing their calendar and planning for their Black Friday/Cyber Monday push. 

As a business, it is essential that you have your calendar planned for November and December so you can get the most out of it. 

From November 1st till New Year’s Day, you can categorize your calendar into before, during, and after. Let’s have a look at how! 

So, let’s talk in the context of the present year, 2023.

  • November 1st

An ideal calendar should start on Wednesday, November 1st.

So, from this day, you should be getting people onto your VIP list and getting them opted in. This is so they can be prepared to mentally plan how much they are able and willing to spend on you or your products. 

You can also offer one or two things, a week or two ahead of time, as some incentive in a particular category. That could be marked down in a special promotion, which will only be available in that window. You will make the early birds happy and give yourself some cushion to get BFCM. 

  • The week leading into BFCM

This is the time when you’re going to want to play the hits, something we talked about earlier. This is when you must ensure your audience is focused and engaged with your brand.

Another beneficial and practical thing to do with your VIP list is that you can also connect to them through SMS. Open things up for your list by connecting to them by different means. This is also one of those times of the year when SMS messages and emails should complement each other. It would be a good practice to send both of these back and forth but aligned and smoothly.

  • Thanksgiving! 

Now, let’s move to the day right before Black Friday. This is when you should be opening things up a little early on, maybe Wednesday or Thursday. 

Thursday would be the day everyone would think about the turkey they’re going to have or the sales they can see on their mobile! So that’s going to be a fine time to open things up so everybody can do their online shopping. 

  • Black Friday and Cyber Monday

Now that the actual day is here, let’s discuss how you will do it. 

Remember not to avoid sending emails more frequently during Black Friday or Cyber Monday weekend, even if you feel uncomfortable doing so.

You could plan your frequency like three emails on Friday, two on Saturday and Sunday following Black Friday, and then sending upwards of three emails on Cyber Monday. This is just an example to give you an idea of how you could go about it. You could plan your calendar according to your requirements and industry.

Sending too much of your content may feel like you need more time. Still, you also want to maximize those days because everyone’s inbox is inundated and complete, and this is the only way you can guarantee you’re at least going to get seen. 

  • Post-BFCM

Now that Black Friday Cyber Monday hype and chaos are over, you don’t have to go radio silent afterward.

Find ways to communicate afterward. Keep sending them updates about your top products of the year. That would be a good practice at the end of the year. It would be valuable to your audience. It will not burn them out if you’re still sending them good content.

Leading into December, you should continue to push hard from the 1st to the 15th or so of the month, leading up to the free shipping deadline.

  • Post-Dec. 25th

And then, after Christmas, following December 25th, you can start with New Year offers like a pre-New Year campaign where the cutoff is New Year’s Day. 

Everyone starts tightening their belts on New Year’s Day, but following the holiday, everyone has gift cards and cash they want to blow on things they didn’t get.

Now, this whole mind map on how to set your calendar in an optimized manner can be a very fruitful experience for you. 

If you can drive two purchases from some of your holiday purchasers, i.e., during November and in December as well, even from 10% of your holiday purchasers, the lot higher volume you’re going to be getting in that window is going to be a massive win because even if you can turn 1000-holiday purchasers into 1,100-holiday purchasers, that’s a high jump.

6. Treating everyone the same

Another mistake we see people making is treating everyone the same and not having a strategy for segmenting their email audiences.  

It is essential that you send a different message to everybody. Only some pieces of content or promotion are relevant to everyone.

  • Relevancy

Again, the importance of relevancy that we talked about earlier in this article. 

Make sure your message is as customized and as contextualized as possible. For instance, if you know one of your customers is purchasing for themselves and another is buying it as a gift, the messages you’re sending should vary according to their needs. 

Connecting the content with the context of their situation goes a long way and doesn’t take much more effort.

  • VIP list

To avoid this mistake, you can ask for that message as a part of the VIP list sign-up. If they get early access, they can trade some data for that. And you can use that data in a forward-facing way to ensure that they will get the correct and relevant messages only. 

  • Segment and exclude

Also, this VIP list will help you segment your audience according to different preferences. It will help you segment those people who have already purchased on BFCM so you can be sure to exclude them for the rest of your BFCM promos.

You would want to give them a little break because sending too much after Cyber Monday would be a lot, and they won’t like it. But then get them with the bounce-back automation that will hopefully drive that second purchase in that holiday window.

7. Not training their audiences

So, do you remember us talking about getting out of our comfort zone and sending more?

Are you increasing your sending frequency during the holidays?

Going from zero to forty emails and messages in one month is not a good look for anyone.

Don’t come off too strong just like that. Be steady and prepare your audience for it. Warm up your audience before the sale season. Get them used to receiving more emails from you. Start by sending them engaging emails that hopefully get them to open and engage with you. 

Don’t do anything out of nowhere; get things lined up, and do that smoothly. But don’t neglect this piece because it will feel so transactional.

8. Not aligning with other marketing activities

As a good marketer, you should know that if your email marketing seems different from the rest of your marketing during the holidays, that’s a big fail. 

You need to ensure your email, SMS, social and website are all well aligned and in harmony (or at least rhyme). They all align with the experience you want to create so that the users have that holistic experience of your company throughout the holidays with clarity and confidence regarding your brand. 

Planning early helps because you can communicate with different teams and different groups across your organization and maximize that time and your customer’s experience.

9. Freaking out on November 10th

The last and most common mistake marketers make during Black Friday Marketing is freaking out on November 10th and getting stressed about almost nothing.

Everyone works so hard to plan and execute an excellent holiday promotion. Everybody gets cold feet when the holiday season rolls out because everybody’s a coward at the starting line.

The nerves and tension get to you; this is bound to happen naturally. What is not okay is losing your cool in the process. This is more about trusting the process and helping your team do the same.

Know that in the states people wait to buy toilet paper between Oct. 31st and BFCM.

Sales will be a little slower, but the pop from the holiday will more than makeup for the slow window.

You should know that you have done your best; now is the time to see the results. You have everything planned for months. Now is the time to follow that plan.

You’ve just got to be willing to be uncomfortable and be ready to go. You had done this before, too, and worked through this, and you’re prepared for this. And now you’re ready to pop the balloon and will see a big blowup!


So, in this article, we have seen the nine most common mistakes marketers make in great detail, but to sum it all up, here’s a list of don’ts for the holiday email marketing strategy for you: 

  • Not planning early enough
  • Playing it safe
  • Not adjusting creativity
  • Not varying messaging offers or experience
  • Not optimizing for your calendar
  • Treating everyone the same
  • Not training their audiences to expect more emails
  • Not aligning with other marketing areas
  • freaking out on November 10th.

Avoid these nine mistakes (or at least most), and you will be in a good place this Black Friday and Cyber Monday holiday. 

It’s not going to be perfect because it never is. Things are bound to go slightly differently than you planned, and that’s where the last point comes in handy again: don’t freak out.

Avoid these nine things, and you’ll hopefully thrive around this time. Also, remember to have some fun while making plans and executing them. Make some sales, and perform the way you’ve been waiting for the entire year.

That’s all from me on this topic. We will have another article on Black Friday and Cyber Monday going into detail about building a specific calendar very soon. 

Until then, if you have any more questions about this topic, let me know in the comments, and don’t forget to give your feedback, too!

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