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7 Strategies for the Breakup Email: The Recruiter’s “Hail Mary”

As a recruiter, you’ve undoubtedly experienced a particular kind of limbo. You’ve sent a sequence of emails to that ideal candidate. In them, you’ve painted a captivating picture of their career trajectory with your organization, catalogued the benefits of working there, shouted out the awards you’ve won. And still, no response. It’s as though you’d have had more success if you’d written directly into the void.

Knowing when to say goodbye is important for a few reasons. For one, if your recruiting outreach isn’t automated—and it should be!—continuing to reach out to non-responsive talent means less time and energy to connect with prospects who might actually be interested. For another, no matter how badly you want a particular prospect to come work for you, too many emails puts your talent team’s reputation on the line and compromises the integrity of your brand.

And so, enter the breakup email.

Admittedly, it’s a bit of a misnomer (“breakup” suggests you were in a relationship to begin with); but the breakup email may be the hook that finally gets talent’s attention. It’s a recruiting outreach email, yes; but it’s also a genre of its own. That’s because it’s doing something different than the other emails in your sequence do. It’s appealing to loss aversion—or FOMO (fear of missing out). That’s what makes the breakup email a secret weapon: It shifts the dynamic and turns the tables. Because in some ways, we never really left high school. (We just said FOMO, after all.) Start ignoring us, and now we want your attention. Confirm for us that we’re not moving forward in the process, and we want to take control of the narrative again. Luckily, the recruiting breakup email is a lot less dramatic than that high school breakup email was.

Of course, not every prospect is going to run back into your patient and forgiving arms: The breakup email has little power over talent who had no interest in your opportunity to begin with. But for those prospects with some interest? It might be the thing that sparks engagement. Indeed, Gem’s data—taken from over one million outreach emails—shows that 22.5% of replies sourcers see are from those final “hail Mary” attempts to reach out. (Note: An outreach platform that offers email tracking will let you gauge recipients’ interest so far. Have they opened your emails once? Multiple times? Have they clicked into your careers page, your employee blog, or your CEO’s LinkedIn profile? Such behavior might give you insights into how effective a breakup email might be.)

When it’s time to cut ties, your breakup email should do a few things:

  • Mention that you’ve tried to connect a few times but haven’t heard back from them
  • Let them know that this is your final attempt to reach them
  • Give them an easy way to contact you if something shifts in the future and they decide to get in touch

These three elements should be in every breakup email you send. But there are some additional strategies that might prompt more replies. Here are some strategies for the breakup email worth experimenting with:

Propose the Relationship Take a New Form

Some of the best breakup emails we’ve seen propose a shift in the sourcer/prospect relationship. Maybe this means suggesting they subscribe to your blog for industry tips, notes on company growth, or product updates (“if you’re curious about what we’re building at any time in the future, feel free to reach out!”). Maybe it means inviting them to your monthly company event (“next month’s talk is about infrastructure automation—I think you’d enjoy it!”). Maybe it means asking them if they have friends with similarly strong expertise to refer (“I have a philosophy that killer SDRs know killer SDRs”). The point here is to recognize that the current dynamic simply wasn’t suiting your prospect. So propose shifting gears for awhile. You can always resume that relationship down the road.

Give Them a Parting Gift

As a recruiter, you’re already in the business of adding value: matching talent whose interests, abilities, and needs align with your organization’s. Offering prospects value in your final email serves as a reminder that that’s your role… and there’s more value for them if they decide to respond. Here’s a goodwill gesture for a recruiting prospect that’s likely to create a positive impression and reap long-term benefits for the brand:

Hi {first name},

The bad news is that I haven’t heard back from you. The good news is that you’re probably loving your current role.

Since it seems the timing isn’t right for us, this will be my last email. But I wanted to sign off with a gift. It’s one of my favorite tools from Sourcing Master Glen Cathey—a Candidate Sourcing Funnel Calculator that helps you estimate how many people you need to identify to find your purple squirrel.

I hope you find it useful.

Remind Them What They’re Missing Out On

Granted, if your messaging has been strong so far, you’ve already given prospects plenty of reasons why they’d benefit from working with your organization. (This is called your employee value proposition, or EVP. It covers everything from career advancement opportunities, to personal development, to company culture, to product innovation, to work-life balance, to vacation.) But your breakup email might include one final teaser. Mention the Friday-Work-From-Home structure you’ve been holding out on telling them about, or the Best Place to Work Award you haven’t yet mentioned. If you’ve done your research—or if you’ve been tracking the links they click into—you know at least a bit about what your prospect is interested in. If they haven’t been opening your emails, maybe this aspect of your EVP goes in the subject line.

Try a Little Humor…

Whether or not you engage in this strategy (and to what extent) will depend on your company’s brand voice, as well as the nature of your recipient. We wouldn’t recommend humor for a prospect for whom all signs point to a grim constitution—though certainly a little lightheartedness can go a long way. Humor can come in the form of gently self-deprecating language (“it’s not you; it’s me”), lyrics from the most popular breakup song of the moment, gifs of puppies crying… you know the range of options; you’ve seen them in action.

… but Be Original

The part about humor being said, let’s extol the virtue of originality for a moment. As a recruiter, you surely remember—perhaps you’ve even used—the infamous “alligator email” that was so wildly popular in sales a few years back. And here’s the thing: It was wildly popular for the simple reason that it worked. Extraordinarily well, in fact. But effectiveness led to overuse, until sales prospects were receiving what amounted to the same templated alligator email from completely different companies in the course of a day.

So while we recommend humor as a strategy, it’s with this caveat: Make it your own, wherever possible. You want your prospect to feel that there’s no way what they’re reading is a template. You want them to hear you. Try a haiku you wrote yourself, or a version of the “roses are red” poem with a creative ending. Try the subject line: “Forget our open role; let’s talk about yoga.” (Make sure they’re into yoga first.) You’ve been a human in the world long enough; you have a sense of what can get a laugh. So go there… but be you as you go.

Send in (or as) the CEO

This is one of our favorite strategies for the breakup email. Maybe you’ve already got your sequence set up to send on behalf of (SOBO) someone else in the organization—the hiring manager, for example. Looping a second person into the outreach can spur engagement: When the prospect believes there’s more than one person with a vested interest in them, and that both people are working together to get their attention, they’re all the more likely to respond. But the CEO exerts a special kind of influence. When the person at the very top of the organization expresses interest in a prospect—regardless of who wrote the outreach—the ego naturally gets involved. It’s a form of flattery, after all. So—with their permission—try drafting the email as your CEO:

Hi {first name},

My name is {name} and I’m the CEO of {company}. {Recruiter} tells me she’s been trying to reach you for the past few weeks to discuss a back-end engineer opportunity. She sent me your LinkedIn profile this morning because she’s not ready to give up on you yet; so I thought I’d reach out myself. Your background is impressive; and I have a sneaking suspicion that our team could offer you a lot in the way of leadership, growth, and an opportunity to take the reins in the disruptive model we’re working on. Would you be up for a conversation this week?

If we received this email, our interest would be piqued.

Suggest a Pause in the Cycle

We don’t have to tell you that one of the most frequent responses to outreach emails is “the timing just isn’t right.” So preempt the response by offering to check in again in 6 months:

I haven’t heard back from you, so I’ll assume a career change simply isn’t on the horizon for you right now. I don’t want to keep hounding if this isn’t the right time. That said, I know how quickly that horizon can change—so I’ll check back in in six months or so and see where you’re at.

You can then schedule a sequence with a new cadence 6 months out, so you don’t forget to follow up on your promise to… well, follow up.

This long-term follow-up strategy achieves a few things at once. For one, it gives your prospect the opportunity to reach out now if they’re not willing to wait six months to hear from you again. For another, it shows a balanced combination of continued interest and a willingness to take their feelings into consideration, ultimately keeping future opportunities on the table. It also gives your prospect plenty of time to consider your offer in greater depth before you reach out again down the line.

So there you have it: 7 strategies for the breakup email. Note that none of the examples above are emotional, desperate, exasperated, or bitter. You’re not here to burn bridges. You know as well as we do that you’re likely to stumble upon their LinkedIn profiles in your next search for that same role.

The breakup email will be as engaging and interesting a genre as you make it. Analytics will indicate what subject lines work best on certain prospect pools, and A/B testing will help you optimize for your audience. Use that data to your advantage… and don’t be afraid to have some fun along the way.

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