Send A Breakup Message

What to do if you really want to get a commitment but don’t hear back from your prospect? You send a first follow up message. Then a second. What now?

Send a third? Or hold off because you don’t want to sound desperate?

Tough choice, time kills all deals. Plus there’s always the opportunity cost of distraction by open deals not moving forward.

Whether you’re fundraising, selling to a customer, trying to close a senior candidate or hear back from a date, here are two ways that could get you back into the promised land:

1. Do something unique that makes you stand out: I can’t give you specific input here as it’s heavily dependent on the situation and needs creativity. Yet, if done well, this is a promising way to get your prospect’s attention back (might be easier for dates vs enterprise sales though …). Here’s a personal example: When I was OOO and didn’t respond to a cold outreach for a few days, a founder followed up by sending me 2¢ on Venmo with the text “Here’s my 2¢ why you should invest in [company name]”. A creative move. Yet also one I’m asking you to PLEASE NOT REPEAT - Venmo is for personal use (sent the money back with a pass note).
2. A bit less risky / requires less creativity: Send a “breakup message”

You heard me right:

Depending on the source, a “breakup message” can get a response rate of up to 76% (though I find this # too high).

Used in a friendly, conversational manner, giving final notice is a very effective way to jolt someone out of complacency and get them moving. For example:

“This is my last follow-up note. If I don’t hear back from you by the end of the week, I will treat this as a pass.”

There are different ways to do this - I’m personally a fan of closing the loop rather than asking for a confirmation of the breakup, i.e. I wouldn’t use:

“If this isn’t for you, kindly let me know so that I can stop contacting you.”

It’s because the clearer you are in terms of this being a final chance, the more your prospect’s FOMO kicks in. Which can be a powerful tool to trigger urgency in them (as we all know from personal experience).

Last but not least, before you start sending breakup messages, here are two more things to be mindful of:

1. Keep them short, simple and professional (don’t sound bitter)
2. Make sure your breakup message actually gets read by writing a subject line that grabs your prospect’s attention, such as “time to part ways”, “my final email”, etc.

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