The breakup email (How to reconnect with a cold prospect)

What is a breakup email?

Treat them mean, keep them keen.

Nice guys finish last.

Unless you’ve been living in the woods away from polite society you’ve heard of the above proverbs.

They apply as much to sales as they do in love which is where the breakup email comes in – it’s basically a last ditch email designed at getting a response from a prospect whose gone quiet.

Why you need to send a last ditch email

A prospect saying no to you is not great but what’s worse is a prospect who strings you along, you feel like you wasted your time and it’ll sting more because you keep thinking of the opportunity cost, all the other fish in the sea you could have gone after. If you leave a deal in indefinite limbo it will mess up your sales forecasting. It’ll make your sales pipeline look healthier than it actually is.

An inaccurate sales pipeline means you won’t know if you’re going to hit your sales quota for the month or quarter. So in this case silence is worse than no. You want to get a response even if it’s to confirm a no.

The breakup email should elicit a response that gives you closure or moves things forwards. It’s a really powerful follow up email but there’s an art to it.

There are a ton of terrible breakup emails out there, mostly because people just copy and paste the same breakup email over and over again, just google the “alligator email”. Basically, a joke is funny the first time round not the 100th time round.

We’ll go through how to write a breakup email, when to send it and the things to avoid. We will even provide some samples but don’t rip them off wholesale – let them inspire you and write them up in your own way so that it isn’t out of character.

When to send a breakup email?

Time is relative, people are busy.

If you’re a sales guy or woman waiting around a week or two is painful. But the prospect is probably busy doing many other things so for them they haven’t actually spent much time on this. They might not have even thought about it.

Therefore, don’t jump the gun. It’ll come across as aggressive. You want to have followed up a few times before via email. Those emails should have been valuable to the prospect demonstrating the value proposition of your offering.

If they were terrible and spammy your breakup email might just get deleted on arrival without being read. Check out our quick guide to writing cold emails where we rip apart some examples of terrible email.

The other factor that determines when you send a breakup email is your sales velocity, basically how quickly a lead moves through your sales pipeline to closing.

If you’ve sent several high quality follow ups and you’re still not getting anywhere and this is taking longer than your average lead time to close a deal then it’s probably time to fire off a breakup email.

Again, this is context dependent – it’ll be different for different people but with the above rules of thumb you’ll know when the right time is.

Subject lines for breakup emails

This is a really important email. You’re about to walk out the door so your subject line should scream that.

There are various ways to phrase that intention, you can ask a question or you can just flat out state it but make sure it’s short and very obvious what this email is going to be about so they will want to open it.

The other nice little touch is to name them so it’s more personal and you’re directly addressing them.

Some examples are:

  • I’m closing your file [Prospect name]
  • Hey {Prospect’s name]! What’s going on?
  • Thanks from RealtimeCRM
  • Are you still interested?

The email body

The first rule is to keep it short. No one wants to hear your life story so at most three paragraphs that are a couple of lines long each.

You want to provide some context for the email i.e. that you’ve been in touch a few times and haven’t heard anything back – this should be one line max, it’s really not the important part so don’t waste valuable email real estate on it.

Now this is optional but you can remind them of your value proposition – whether you do so or not depends on the kind of breakup email you’re trying to write.

What that means is there are breakup emails and then there are breakup emails that are short, sharp and make the decision for the prospect. You don’t ask them to walk away you do it and it’s on them to ask you to come back.

The other part is some acknowledgement of their time. Try to be understanding of the fact that they’re busy and that you’re grateful for the time they gave you.

Lastly, it’s your call to action. What do you want them to do? It can be asking them do you want to close their account or that you’re closing their account but they can get touch with you when they’re ready to kick things off again.

Those are the main beats your breakup email will cover. You can add some humour if you want but make sure it’s actually written by you and not some cookie cutter breakup email template you took like the alligator email which everyone now knows.

Don’t be intimidated by it – it’s only a few paragraphs so anyone can write one. Rocket science is complicated, reconnecting emails are not.

If you want more help on writing emails check out our cold email cheat sheet it’ll walk you through how to write them, and it’s got over 10 proven email templates to help inspire your own.

Breakup email mistakes to avoid

Here are a list of things you should not do when writing a breakup email:

  1. Avoid being accusatory or disappointed in tone – try to be positive or neutral.
  2. Don’t come off as desperate or pushy – send it to someone else in your team to get a second opinion before you send it to the prospect to be sure of this.
  3. Don’t make the email about you but about the prospect and the value you’re offering them. The time you’ve spent on chasing them is not important to them.

5 Breakup email templates

Remember to use these breakup email templates as inspiration – rewrite them in your own words so it doesn’t come off as too contrived and out of character.

Breakup email template 1:

Hi [Prospect],

I’ve reached out to you a few times about [value proposition] but haven’t had a response from you yet.

I understand if you’re busy or if you’re not interested so this will be my last email to you.

If down the road you change your mind then I’d love to hear from you and we can get the ball rolling by setting up a [call to action; phone call or meeting].


[Your Name]

This breakup email works because it doesn’t completely shut the door on the prospect but leaves the ball in their court to try again at a later date. It also reminds them of your offering without being too pushy.

Breakup email template 2:

Hi [Prospect],

My name is [Your Name] and I’m the Managing Director of [RealtimeCRM].

[Sales Rep] informed me that you recently had a demo of RealtimeCRM and I wanted to check in with you to hear your thoughts.

I’d love to hear from you and if you have any further questions fire away and I’d be happy to help.

Best regards,

[Your Name]

This email works because you’ve brought out the big gun. The boss which makes the prospect feel important. It really works sometimes to rub the ego to get a response. We used to have a customer back in our software development days whose email address was [email protected].

I need say no more. Status, power and acknowledgement matter a lot to some.

Breakup email template 3:

Hi [Prospect],

I hope you’re doing well. I’m getting in touch because I haven’t heard back from you in a while and I’m in the process of reviewing and cleaning up my list of opportunities.

Since there’s not been any movement in a while I’m assuming [offering] is not of interest to you at this time, therefore can I close your file?

If you are still interested let me know and we can discuss the next steps to help you achieve [objective].

Best regards,

[Your Name]

This one is great because you’ve got a good reason for getting in touch. It’s just normal standard procedural stuff. The other awesome feature is you give them an out, a lot of people want to avoid conflict and are awkward about saying no.

If they don’t want to say yes then we want them say no because that’s better than silence.

Breakup email template 4:

Hi [Prospect]

I haven’t heard back from you in a while. I understand if you’re busy and [product/service] isn’t a priority at the moment.

I’m happy to press pause for the moment and what I’ll do is check back in with you in say 3 months time. Hopefully then we’ll be more aligned.

Best regards,

[Your Name]

This email works really well because it allows you to follow up later on. Sometimes the prospect is interested in pursuing the deal but the timing isn’t right. This email acknowledges that and also tells them what will happen down the road.

It takes the pressure off of them and leaves things in a friendly place ready to begin again at a later date.

Breakup email template 5:

Hi [Prospect]

I haven’t heard back from you in a while.

I wanted to check in one last time because I think [product/service] would really help you to [problems solved] and so [achieve goals].

But hey if you’re not interested I totally understand so let me know and I’ll close your file.

By the way here are some resources that can help with your [business challenge]:

  • Resource 1
  • Resource 2

Best wishes,

[Your Name]

P.S. If you’re still interested in proceeding but now is not the right time let me know and we can press pause and pick this up in 3 months.

With this email you’ve clearly stated the value proposition and you’ve given some useful resources away as a thank you for reading the email but also to show that you have value to offer them.

Plus you still leave the door open without coming across as pushy. It strikes the right balance between walking away, demonstrating value and leaving the door open for the future.