Monica Badiu, Email Copywriter & Copy Coach

Email Re-engagement Before Black Friday

Estimated reading time: 10 minutes

A subscriber who stopped clicking your emails may have lost interest. They may also have finished the course, solved the problem, or reached a stage your current content no longer addresses. Those situations need different responses before you invite everyone to your Black Friday sale.

Email re-engagement gives you an opportunity to find out what has changed. Used well, it helps you decide who should receive your promotion and which message or offer is relevant to them. That is more useful than collecting a few extra opens and returning every respondent to the same campaign.

For this episode of Master The Inbox, I reviewed two inboxes I use for email research, focusing on re-engagement, list-cleaning, and win-back emails received during September. The examples showed several ways to restart a conversation. They also revealed why the action you ask for matters as much as getting a response.

Table of contents

Start before you increase promotional sending

Black Friday often changes several things about an email program at once. A creator who normally sends one educational email a week may start sending three or four promotional messages. They may also decide to include contacts who haven’t received regular emails in months.

The total number of contacts in your platform doesn’t tell you how many people expect those messages. A database of 70,000 could contain recent subscribers, active students, former buyers, long-term inactive contacts, and people whose original reason for joining no longer applies.

In the episode, I recommend starting re-engagement weeks before Black Friday, ideally during September or October. That gives you room to ask questions, interpret responses, and adjust your promotional audience. It also avoids making your busiest sales period the first time you investigate an old segment.

Begin by comparing the audience you email regularly with the audience you intend to include in your promotion. If they differ substantially, identify who the additional contacts are and what you know about their recent relationship with you.

Give subscribers a reason to respond before asking for confirmation

One course creator I’d followed for about four years sent a two-part re-engagement sequence. The first email used my name as the subject line and “Still there?” as the preview text. It explained that I appeared not to have opened recent emails, while acknowledging that open tracking was imperfect.

The email offered four free templates for inviting customers to feedback calls. That gave me something useful to engage with, connected to the sender’s work. There was also an option to unsubscribe.

Five days later, after I hadn’t taken action, a second email arrived with a clearer instruction: click to stay subscribed. It said that without a response, I would be removed after another two days.

That sequence combined a helpful invitation, a direct permission check, and a stated next step. It is an example of how one sender approached the task, rather than a universal seven-day schedule every business should copy.

Open data deserves care when defining inactivity. Apple’s Mail Privacy Protection can prevent senders from knowing whether someone opened an email. A clear answer about preferences or current needs gives you information that an open alone cannot provide. Apple explains Mail Privacy Protection here.

Choose a resource that fits the reason a particular group joined your list. Then decide what response you need and explain what will happen if they don’t respond. Make leaving straightforward from the first message.

A previous customer brings a different history to the conversation

Another example came from a streaming and community platform I had previously paid to use. Its emails invited me to return as a member, using content and an offer to make that return appealing. Later emails introduced deadlines for the offer.

This was a customer win-back campaign with a re-engagement function. Its purpose was to encourage another purchase, rather than simply confirm whether I wanted to remain on a mailing list.

For course creators, purchase history can help you make the invitation more relevant. Someone who bought a beginner photography course has a different relationship with you from someone who downloaded a checklist. Your message should acknowledge that difference.

You could ask whether the former student is still practising the skill, share what has changed in the program, or suggest a next step if they completed it. Be careful to distinguish a purchase from completion: buying the course doesn’t establish that they finished it.

Before drafting, identify what that group bought and what a useful next conversation might be. The first objective is to reconnect with their situation, even if that conversation eventually leads to another offer.

Ask about the problem that brought someone to your list

“Are you still interested?” leaves a lot unexplained. Interested in your business? In solving the original problem? In receiving weekly content? In buying a course this month?

In the episode, I use a hypothetical Spanish-teaching business to show a more specific approach. The question could be, “Are you still learning Spanish?” The answers might be “Yes, actively,” “Yes, but inconsistently,” and “Not right now.”

Those answers help describe a learner’s current situation. They also give you a starting point for choosing what to send next, without making a free resource the only reason to click.

A business teaching people to launch courses could ask where subscribers are with their first launch. Someone who has launched, someone still working on it, someone who paused, and someone who changed direction shouldn’t automatically receive the same beginner pitch.

Use a question you can act on. If the answers won’t change the content, support, or offer you send, narrow the question until they will. Configure and check the corresponding tags or segments before sending the email.

Match your interpretation to what the subscriber clicked

A coupon can be appropriate when your objective is to encourage a purchase. But clicking to view a discount doesn’t answer whether someone wants your regular newsletter.

I received a “we miss you” style email with a $5 coupon from a brand I had never bought from. It was a useful reminder that win-back language can fail to reflect the recipient’s actual relationship with the business.

For your own list, keep the meaning of the action in view. A coupon response can suggest interest in an offer. A preference selection tells you what content someone chose. A reply may explain the obstacle that has stopped them moving forward.

Look at those actions alongside other relevant behaviour before deciding the next message. A coupon click by itself doesn’t prove purchase readiness, and confirmation of a subscription doesn’t establish that the person wants every promotion.

The practical question is simple: what did this person actually tell you? Record that information accurately rather than treating every response as the same kind of renewed interest.

Consider whether your subscriber’s needs have changed

When I worked on marketing for a luxury bridal brand, some subscribers had already had their weddings. Their original reason for joining the list had ended. Continuing to talk to them as prospective brides would miss that change.

The same pattern appears in teaching businesses. A puppy-training subscriber may still care deeply about their dog two years later, but need something different from the content that first attracted them. A learner who finished a beginner course may now be looking for more advanced help.

Before treating silence as a rejection of the whole business, consider whether the topic still fits. A short status question can help you find out whether the problem remains, has changed, or has been solved.

Sometimes the answer will reveal a useful next step. Sometimes someone will no longer need your work. Both outcomes help you make a more appropriate decision than repeatedly sending the original message.

Separate the groups before planning the sequence

Start with distinctions that change what you would say. Recently engaged subscribers can continue receiving useful content while another group goes through re-engagement. You don’t need to pause the whole list.

People who engaged until recently may need a different invitation from those who haven’t interacted in a long time. Past customers may warrant a message based on what they bought. People who read consistently but haven’t purchased present another question entirely: what is preventing the next step?

The level of detail should fit your business. A small group of former students may be easier to contact personally than to put through a complicated automation. A larger audience may justify more segmentation where you have useful data to support it.

Your historical buying patterns can also inform how you define inactivity. Consider how long customers typically take to purchase and which interactions you can observe. The transcript does not prescribe a universal number of inactive days for every list.

Plan what happens after each response—and after silence

One possible sequence starts with a relevance question, follows with a useful resource, offers preference choices, and ends with a clear permission check. You can adapt those steps to the segment rather than insisting that everyone needs four emails.

Preference options can include topics, reduced frequency, or a break from the promotion, where your setup supports them. If you offer a choice, make sure the subsequent campaign honours it. The point is to let the subscriber influence what happens next.

For long-term inactive contacts who don’t respond, consider excluding them from your heavy promotional audience. Suppression from a campaign and permanent deletion are separate actions. The right treatment depends on your platform, customer records, and the relationship you need to maintain.

In the episode, I mention the possibility of reassessing some contacts after the season. That should remain a deliberate decision based on their status and permission, rather than an automatic resend to everyone who stayed silent. People who unsubscribe should remain excluded from marketing.

What to do this week

Build one useful re-engagement path before expanding the project:

  1. Choose a group with a shared history. Use one lead magnet, purchase, or period of previous engagement to make the message specific.
  2. Ask what has changed. Draft one question and three or four answers that reflect realistic stages in their progress.
  3. Plan the follow-up. Decide what each answer changes about their content, offer, or campaign inclusion.
  4. Set the permission and nonresponse steps. Make preferences and unsubscribing clear, and determine which inactive contacts will stay outside the promotion.
  • If you only have 10 minutes today, draft the status question for one lead magnet. That small step forces you to think about the person’s current need, rather than relying on the reason they subscribed months ago.
  • Re-engagement can improve your understanding of who is still on the list and what they want from you. That information gives your Black Friday messaging a more relevant starting point and helps you make considered decisions about who receives it.
  • Explore this episode on Master The Inbox.
  • Build your campaign with Revive Your Email List, which covers identifying disengaged subscribers, planning the emails, and handling the responses.
  • Monica Badiu is a conversion strategist, email copywriter, and host of the Master The Inbox podcast. She helps course creators build email strategies that sell — without the pressure tactics, the spam, or the burnout.

Monica Badiu

About the Author

Monica Badiu is an email revenue strategist and conversion copywriter who helps course creators turn their email lists into reliable revenue systems.

With over 17 years of marketing experience and more than 25,000 hours spent studying and practicing customer-centric email marketing, she specializes in diagnosing the gaps that prevent email from performing at its full potential. Her strategies have helped course creators generate over $3 million in revenue, and her work focuses on building thoughtful email systems that drive sales while strengthening genuine relationships with audiences.

Leave a Comment