9 Biggest Holiday Email & SMS Marketing 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 and the holiday season can be rather intimidating. So much of this planning falls squarely on the email marketer, who is responsible for building anticipation, building a list, and converting that list when it matters most.

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 how to maximize their email marketing during 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

Needless to say, 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 important 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 looking back on what has and hasn’t worked in the last few years and what you can leverage this year. 

You should start planning your goals and requirements for fulfilling those goals. So that once your buildup for the holiday season starts in late October or early November, you have the majority of your assets ready to go. Your focus gets to move to focusing on being proactive in your efforts as opposed to being reactive to what you need to do.

Suddenly you are pressing play on the content, campaigns, messaging and creative, you had been working 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 your mind. That is what will allow you to maximize and make effective use of all the opportunities presented to you during that time.

So start planning, start brainstorming and start looking for ideas and start taking suggestions from your creative team so you can actually 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 get you in danger! 

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

  • Zig when others are zagging 

This is where you need to be asking 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 to hold themselves back while sending out emails. For example, 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. 

What they don’t realize is 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 making good use of your best-performing subject lines. For example, the subject lines that have given you more open rates previously, contextualizing and using them again might be of great benefit. You may also have some fun using emojis in the subject lines of the email content, which would make 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 also borrow ideas from other industries and make use of them and modify them according to your requirement. These ideas, as taken from outside, would be something new in your industry and will hence, let you stand out against other brands and businesses in the industry. 

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

For example, you can borrow ideas from other industries in terms of how you’re going to 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 be distributing and sharing 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 need to make sure your offers are unique and something that you or anyone in the industry never offered. That is one thing that will attract your audience, but there is something else too. 

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 in case you’re not giving any offers, communicate that early too.

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

  • Limited time offers 

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

People tend to get the same offers over and over during the holiday season; that’s why scarcity and limited-time offers play a vital role in bringing the audience to your brand by interrupting the pattern of what they are getting.

3. Not adjusting creative

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

Just the way, 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 touch to them, or you can also change the popover designs for holidays only. 

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

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

Apparently, doing all these things is not much big of a 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. Making sure that you are sending the right messages to the right audience, a message that lines up with their requirement, is crucial. 

You can also include countdown timers. However, make sure not to overdo it, 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. 

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You may also include callout to the sales and the promotions that you’re going to be doing on Black Friday and Cyber Monday in your automation. As we mentioned before, 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 over and over again 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 really excited and also engaged in what you’re offering.

  • Design popovers

During holiday sales, you can also design popovers for your websites that would 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 special 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 low hanging fruit technique, like sending them a collection of products that are easy for them to purchase around specific holidays.

  • Open up your list

It is also at this time of the year you may decide to open up your list. 

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

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

  • Adjust the trigger flow

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

It is okay to be a little aggressive with your emailing in times like these because people are engaged in a lot of other things. There might be a lot of other 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, can pull them through.

5. Not optimizing calendar

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

As a business, it is important 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 break down and 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, 2022.

  • November 1st

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

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

You can also offer one or two things probably the week or two ahead of time, as some type of incentive in a special category. That could be marked down in a special promotion which is only going to be available in that window. You will make the early birds happy and give yourself some cushion going into 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 have to make sure that your audience is focused and engaged with your brand.

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

  • Thanksgiving! 

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

Thursday would be the day everyone would be either thinking 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 be opening things up so everybody can be doing their online shopping. 

  • Black Friday and Cyber Monday

Now that the real day is here, let’s talk about how you’re going to go about it. 

One thing you need to remember is not to shy off from sending emails more frequently during Black Friday or Cyber Monday weekend, again 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 on Cyber Monday, sending upwards of three emails. 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 requirement and industry. 

Sending too much of your content may feel a little bit over-do, but you also want to be maximizing those days because everyone’s inbox is inundated and full, 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 is over, you don’t have to go radio silent after that.

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. If you’re still sending them good content, it is not going to burn them out.

Leading into December, you should continue to push hard from the 1st to the 15th or so of the month. Basically 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 Years 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 huge 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 how to segment their email audiences.  

It is important that you do not send the same message to everybody. Not every piece of content or promotion is 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 purchasing it as a gift, then the messages you’re sending to both of them 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 messaging 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 make sure that they’re going to get the right and relevant messages only. 

  • Segment and exclude

Also, this VIP list is going to help you segment your audience according to different preferences and is going to 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 for sure. But then get them with the bounce-back automation that is hopefully going to 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?

Increasing your sending frequency during the holidays?

Going from zero to forty emails and messages in one month is not a good look on 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 with sending them engaging emails that are hopefully getting them to open and engage with you. 

Just don’t do anything just 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 than the rest of your marketing during the holidays, then that’s a big fail. 

You need to make sure your email and SMS, your social and your website are all well aligned and are in harmony (or at least rhyme), and they all line up with the experience you want to create so that the users have that holistic experience of your company throughout the holidays without any confusion and doubts regarding your brand. 

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

9. Freaking out on November 10th

Now the last and the 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 a really beautiful holiday promotion, and when the holiday season rolls out, everybody gets cold feet because everybody’s a coward at the starting line.

The nerves and tension get to you, this is bound to happen; this is natural. What is not okay is losing your cool in the process. This is more about trusting the process, and help 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 make up for the slow window.

You should know that you have done the best you could, and now is the time to see the results. You have everything planned for months. Now is the time just 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 are going to 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 of them) and you are going to 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 different than you planned, and that’s where the last point comes in handy again, don’t freak out.

Avoid these nine things, and you’re hopefully going to 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’re going to 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 relating to this specific topic, let me know in the comments, and don’t forget to give your feedback too!

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