The Stupid Sales Email Technique I've Been Arguing About for 30 Years

In the past 30 years, I’ve listened to a lot of smart sales leaders and experts tell me breakup emails are effective.

I respect these people deeply — but none of them have ever convinced me. If it were up to me, salespeople would never send breakup emails.

How Breakup Emails Work (In Theory)

Quick summary to make sure we’re on the same page: A rep sends a breakup email after she’s attempted to contact her prospect several times with no response. She writes, “I haven’t heard from you, so I assume this isn’t a priority. If you don’t answer, I’ll take you off my list.”

A very small percentage of buyers — maybe one or two — will reply apologetically:

“Sorry for not responding, I’ve been slammed. It’s not a good time right now, but maybe try me again next quarter.”

The salesperson responds, “No problem, I’m glad to hear from you. I’ll reach out in August.”

She puts that opportunity back in her pipeline for August. At this point, she’s feeling great about the breakup email. It worked — at least if you define success as getting a reply.

Yet when August rolls around and the rep tries to get the ball rolling again with the customer, he’s still not interested.

The Net Results of Breakup Emails

I see zero benefits to sending breakup emails.

You might get replies — in fact, reps always tell me they get their highest response rate from breakup emails — but you’re not actually closing deals.

During my first years in selling, I worked at a brokerage firm where the common practice was to leave customers voicemails in a grave tone:

“Hi David, it’s very important I hear back from by the end of the day. I can be reached at [number].”

The seriousness combined with the ambiguity almost always resulted in call-backs. But did those people become customers? No. As soon as they realized what the call was about, they hung up.

The end result of sending a breakup email versus not sending one is the same: No opportunity.

And there are significant downsides.

First, this approach makes you look desperate. You’re “breaking up” with someone who’s already breaking up with you. In addition, it makes the power dynamic even more imbalanced. The buyer wonders why you’re spending so much time and energy on them when they haven’t indicated any interest. They’ll decide your product isn’t valuable or your services aren’t in-demand.

Neediness is the nail in a salesperson’s coffin. Prospects won’t take you seriously, let alone buy your offering.

Second, you’re sabotaging yourself with the buyers who don’t respond. Let’s say you send 100 breakup emails over 12 months. Five to 15 prospects write back, “I’m sorry, call me later.”

That means 85% of your recipients are thinking something like, “Why won’t this person get the hint? Stop sending me sales emails.”

In time, many of these buyers will become better fits for your product — maybe they change jobs, get promoted, discover an emerging problem, or launch a new program or project. But because you’ve created a bad name for yourself, you probably won’t be their first (or even their fourth) choice.

Which brings me to my third point: Do you truly want to remove these prospects from your pipeline forever?

Of course not. You want to reach out again next quarter to see if their situation has changed. When buyers get your email a few months down the line, they’ll know your breakup email was just a bluff.

When to send breakup emails

If you must, you should only send breakup emails when you have an existing relationship with the prospect. If you’ve been emailing a prospect you’ve never actually connected with — you have no relationship to break up from, so a breakup email won’t mean anything to them.

The Best Alternative to Sending Breakup Emails

During every sales training, I give reps the same message: The leads you’re working aren’t yours. They belong to your company. It’s an honor to care for the leads you’ve been provided with, so do it with dignity.

If you don’t want to poison your company’s reputation and ability to work with future customers, don’t send breakup emails.

You might be wondering what you should do instead.

I suggest nothing.

After several attempts with no response, put the buyer on a list of contacts you’ll try again on a future date.

I often find that when a rep reaches back out in several months, her prospect will say, “You tried to reach me in the year — I’m sorry I never got back to you. We’ve had some changes since then. I’d like to learn more about your product.”

The salesperson can respond, “Don’t apologize. I email hundreds of people, so I don’t remember the ones I sent you. I’m glad we’re talking now.”

Not only does this reply put the buyer at ease, it also makes the rep seem confident, controlled, and credible.

Chasing a prospect is inherently risky: It puts your perceived authority and power in danger. There’s no way you should compound that loss with pushy tactics like sending a breakup email.

Other Alternatives to the Breakup Email

Start a new thread

When a conversation stalls with a prospect, try starting a new thread over a new event. Pick an event that’s relevant to them or their company, such as, “I saw a press announcement your company will be at Trade Show X this summer. Will you be attending?” Let your prospect know they don’t have to feel guilty for not calling back and give them an open door to walk through.

Ask for help

If a deal is humming along and the prospect stops responding, I’ll ask another rep or manager to engage on my behalf. They reach out to the prospect as if they aren’t aware the deal has stalled. A simple message like, “I’m looking forward to hearing your feedback on the demo you had recently. What’s your availability this afternoon?

Salespeople don’t walk into a room with a lot of weight, so we can’t give away more than we have. If a prospect doesn’t respond after a week, we both know they’ve lost interest. But, because you haven’t said the words, I’ll have my boss follow up where we left off.

The prospect never said they didn’t want to do business me, so having my manager or colleague reach out pushes for either a “Yes” or a “No” and allows me to discern how to move forward.

Go around the prospect

The most extreme next step is to go around the prospect. But before I advise someone to take this action, I ask them to imagine what they would have done to avoid being in this position. It’s wise not to lean on this strategy too often — and to get to the root of why you’re faced with this challenge in the first place.

And remember, if you’re in this situation, it’s likely nothing will save the deal. If you go around a prospect, start by sending them some information.

It might be marketing collateral that’s only available internally, but it should be designed for breakups. Send the white paper or case study and ask the prospect to call when they’re done reading it.

What do you think: Are you a believer in breakup emails? If you can show me one piece of data that this technique pays off, I might change my mind. Please leave your opinion in the comments so we can get a thoughtful discussion going.

Looking to go deeper into efficient and effective prospecting techniques? Check out dates and locations for my prospecting workshops. Learn more.

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