True Crimes: Threatening Sales Emails

Sales criminals are always pushing the boundaries with terrible cold emails, and they’ve done it yet again. A menacing sales rep is on the loose, spamming inboxes, and annoying prospects at every turn. Unfortunately, this rep isn’t just sending out badly-written cold emails – he’s graduated to actually threatening prospects in the hopes of closing a deal.

What you’re about to see is an actual sales email that we’ve received in our own inbox, with names and pertinent details redacted. Prepare yourself – these sales crimes are real, and so are the misguided sales reps who hit send. We hope that by analyzing the worst of the worst sales emails, you will never make these terrible sales mistakes yourself.

Some sales reps have no idea how to write a sales email. These are their stories.

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The Scary Subject Line

You know what people respond positively to? Threats. Oh, wait, that’s completely wrong. People hate being threatened, and tend to react badly when you try to force them to do anything against their will. But this sales criminal simply can’t seem to resist using a tactic usually reserved for mob bosses and kidnappers – an ultimatum.

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Instead of writing an intriguing or informative subject line to coax a prospect into clicking, this sales rep is instead threatening to digitally stalk prospects. Oh, you promise you won’t contact me again if I respond? How nice of you. This rep is lucky that anyone at all opens this email with a subject line like that. Even if a prospect is interested in buying branded apparel, this is sure to make them run in the opposite direction and buy from literally anyone else in the industry.

Even worse, the content of the email makes it clear that the rep has done no research about the prospect, and doesn’t even know if he’s emailed the decision-maker. He asks the prospect for help, instead of offering help and value to the prospect. Why would any prospect help someone who is threatening them? And in case you missed the subject line, this rep helpfully included the same ultimatum in the P.S., emphasizing yet again that he thinks this is a great way to connect with prospects. Luckily, modern inboxes have a handy tool that allows you to block unwanted spam.

While this may sound harsh, there is probably a reasonable and all-too-common explanation for this terrible email. The rep has probably resorted to a threat out of desperation, because he’s under pressure to close deals and hit a number. While this is no excuse, it does explain why someone might take a risk and use this completely misguided tactic. Unfortunately, the rep is unlikely to close any new business with this sales pitch. If anyone even responds at all to this email, they’re more likely to tell the rep to take a hike than to sign a contract.

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Improving the Pitch

No one enjoys being threatened, and no one wants to work closely with a rep who believes this is a good approach to selling. Instead of pestering prospects with multiple emails, this rep should take a more targeted approach and be more accepting of rejection. The product he’s selling – branded apparel – is something that many companies are interested in, so he shouldn’t have to resort to threats in order to close a deal.

A better email would be addressed to companies in a relevant industry, with a thoughtful and polite message about branded apparel. For example:

Hi Sam,

I saw that InsightSquared is growing fast and hiring a lot of new employees – congratulations! I thought you might be interested in buying some branded apparel for your newest hires. Branded clothing not only makes your employees happy, it also helps advertise your business every day they wear it.

I’d be happy to talk with you about our various styles, customizable options, and prices. Let me know if you’d be interested in learning more.

Sales Rep

This email is much friendlier, less aggressive, and much more likely to earn a response from prospects that receive it. While it’s true that there’s a lot of competition out there and reps need to stand out, sometimes you can stand out too much, and hurt your own sales efforts by threatening the people you’d like to impress.


Hopefully, now you will never receive or even think of sending out a cold email using this type of terrible sales tactic in the future. Keep an eye out for the next edition of True Crimes: Cold Sales Emails for more lessons in perfecting your pitch.

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