Breakup Email: The Hail Mary in your Sales Outreach

(Last Updated On: November 22, 2017)

What should you do, when after multiple touches and attempts, your prospect hasn’t responded to any of your emails?

You bring out the Hail Mary play.

We have all been there. You have a prospect who you think will be a great fit for your offer and all you want is that 15-minute slot on her calendar. You have tried emailing, calling, even sent a tweet and Linkedin Inmail her way. Your email tracking software tells you that your emails are getting delivered and opened. But the reply continues to evade you. All you have is deafening radio silence from the other side.

Ready to give up and move on? Not yet. It’s time to get personal and unleash that little weapon called the Breakup email, from your arsenal.

The intention behind the breakup email is to tell the prospect that you are “moving on” as your attempts to reach out have been in vain.

But why would we do that? No self-respecting sales person ever really gives up. What we are really trying to do is to change the balance of power in this one-sided equation and make your outreach look more important by invoking the “scarcity effect”.

When things become less available, they become more desirable. The breakup email uses this principle to persuade your prospect to hit reply.

To quote Robert Greene from The Art Of Seduction:

The greatest mistake in seduction is being too nice. At first, perhaps, your kindness is charming, but it soon grows monotonous; you are trying too hard to please, and seem insecure. Instead of overwhelming your targets with niceness, try inflicting some pain. Make them feel guilty and insecure. Instigate a breakup — now a rapprochement, a return to your earlier kindness, will turn them weak at the knees.

If “monotonous and trying too hard to please” sound like words that describe your sales outreach, then the breakup may be just what you need to turn things around. 

breakup email

Enough with the baptism already.  Let’s get down to actually writing the Breakup Email.

How to Write a Breakup Email

To wit,

  1. What should the “hook” or the subject line look like
  2. What should the email body contain
  3. And what is a good call to action to wrap things up

1. Subject Lines for a Breakup Email:

Your relationship with the prospect has reached a critical fork. You are making a painful and important decision to part ways. There is tension in the air. And you want your prospect to notice it.

If there is one place where you can go overboard on emotion, it is the subject line of your breakup email. Channel that inner drama queen as you write this subject line.

The worst thing that can happen at this stage is for your prospect to ignore this email and bring your last ditch attempt to a premature end.

Sample example subject lines for a breakup email:

2. Email body for a Breakup Email:

While keeping the emotional tension from the subject line alive, there are a few key points to be made here:

  1. Set the context by explaining that you have reached out a few times
  2. That this may be the last time they will hear from you in a while
  3. Reiterate the value that you are still willing to provide

The content of the email can be constructed using various techniques.

  • Remind them that you have reached out a few times: 

    It is important to set the context and remind them that you’ve reached out to them multiple times and still haven’t gotten any response.

Sample Example:

  • Reiterate the value that you are still willing to provide:

    This may be the final opportunity to remind your prospect what you do and how you can help them. Sell the sizzle one last time.

Sample example:

  • Ask them why they didn’t respond:

    Indicate that you are stopping your followup. At the same time, instead of another sales pitch, if you ask them why they chose to not respond, they are often willing to provide constructive feedback – which can be a great conversation starter.

Sample example:

  • Let them know that you value their time:

    Another theme for your Breakup email is letting them know that you value their time. Hence you are stopping your followup to give them some space.

breakup email 3

Sample example:

  • Take the deal away:

    Your prospect has not replied but has not unsubscribed either. By taking the deal away, you can actually make it look more attractive and push interested prospects in getting back to you faster.

Sample Example:

  • Be Humorous:

    Nothing makes for a memorable goodbye than some humor. Get your prospect to chuckle and create a strong last impression. It increases the chances of a reply – when they realize what a fun conversation they could be missing.

Sample example:

3. Call To Action (CTA) for a Breakup Email:

The call to action on a breakup email plays the role of keeping the door open – should the prospect choose to reciprocate and reply back.

Sample examples:

Mistakes To Avoid in a Breakup Email:

The breakup email is a tricky one. One needs to use just the right bit of emotions. Without sounding desperate or pushy.

Just because you reached out to a prospect, it doesn’t mean that he/she owes you a reply. While there is a minor element of guilt-tripping involved, keep it light and positive. Don’t accuse the prospect of not replying. They may have countless reasons to why they haven’t responded and frankly, they don’t owe you an explanation too.

And its, It’s not all about you: The breakup email isn’t about you or how you contacted your prospect or how long you waited for a reply. It’s about you valuing their time, it’s about what you’re offering, it’s about respecting their space and decision and backing out at the right time.


As a sales-person, the worst answer is not a NO.

It is “silence”.

‘Yes’ is obviously the answer you are hoping for. A No is still fine because you can close the file and move on to the next prospect. What leaving you hanging in the balance is the silence.

The breakup email is a great option to use in these scenarios to convert silence into a conversation.