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The Five (Or So) Worst Cold Emails We’ve Ever Seen

a woman screams in front of a computer screen with a list of inbox messages

Every morning I get into the office and open my email, where I am immediately greeted by roughly 283 unopened messages, 95% of which are cold emails from salespeople.

As the day goes on, more salespeople dump more cold emails into my inbox. And like clockwork, I delete nearly all of them—most of those without even reading them. The ones I do read tend to be exactly what I expected: a salesperson who didn’t really do their research and shouldn’t be reaching out to me.

Sometimes the emails are too long, sometimes they’re too short. Sometimes I have no idea what they’re about or what action the sender wants me to take. Sometimes I’m pretty sure the sender doesn’t even know who I am. On a very rare occasion, I come across a cold email that I actually read, find useful, and respond to. And sometimes (less rarely), I am actually surprised by the sheer awfulness of the email.

Over the years, I’ve had some stupendously bad cold emails invade my inbox. In fact, sharing the worst of the worst has become something of an office sport among my colleagues. And now, I’ve decided to compile a cold email Hall of Shame so that we can all learn from past mistakes and get better at this critical form of sales communication.

Now, before we start with the list, let’s lay out what a good cold email should do so that we’re all on the same page.

A good cold email should:

  • Have an eye-catching (but not obnoxiously so) subject line. Typically, a good subject line includes the recipient’s first name and a short, specific message.
  • Come from the salesperson specifically, not a company. Cold emails are all about forming a personal connection; the “from” field should suggest that an actual human being is writing to you.
  • Include short body copy that is reminiscent of what you would say to that person if you were introducing yourself at a conference.
  • Specifically mention why you are interested in working with the recipient. Do your research and understand who that person is and what their company does. You should truly believe that you are providing this person with a service that will actually help them. If you’re just trying to meet your quota, it’ll show. Additionally, this advance research will help you catch your reader’s attention. People like hearing about themselves.
  • Include trust factors. If you have a big name client, or a client you know your target will have heard of due to their shared industry or geographic location, you should mention them in your cold email. If you have an impressive number of clients, that can also be effective. (Sometimes quantity is quality.) You just want to let the recipient know that you are the real deal.
  • Have a clear CTA. There should be no doubt in the recipient’s mind regarding what to do next after reading your email.

That said, here’s a link if you need to study more best practices.

Without further ado, let’s get into the reason we’re all here: the worst, most cringe-worthy cold emails of all time.

To prevent eye-strain, click any of the emails to see full-size versions, and please note that I have blacked out all personal information for the protection of both the senders and receivers of these emails.

1. The Possible Serial Killer

My colleague received this email from someone we hope is a well-intentioned though misguided sales rep, but who actually comes off as a potential stalker targeting female office workers.

The problems:

  • While the subject line is short, specific, and includes the recipient’s first name, it has an insinuating, almost flirtatious quality that makes it feel inappropriate. Not the strongest start.
  • Next, the body copy includes nothing about who this person is, what service they offer, why they want to work with my colleague—or even why they want to send her a package in the first place. Rather, he just says he wants to send her an unspecified item (anthrax?) in exchange for some very personal information. That’s a hard pass, for me.

2. The Colossus of Cold Email…and Random Cat Memes

You should probably make sure that you are sending flawless cold emails before you start calling yourself “The Colossus of Cold Email,” otherwise you might end up on this list.

The problems:

  • The subject line is not great in my opinion, but my coworker opened it, so I guess that counts for something. The sender himself claims to have a 74% open rate on this email, which is so far above the average that I can’t help but be skeptical.
  • The formatting of this email is terrible and makes it very hard to read. There’s no clear CTA, either. Am I supposed to unsubscribe? That is, after all, the first and clearest of what could be labeled a CTA in here.
  • Next up: a little personality in a cold email is great. Overbearing personality, though? Not so much. The opening line “If you haven’t guessed yet, I happen to be one of those people that loves a good cold email. Am I just that sick? Maybe…” is the definition of overbearing. I guess this is a joke, but I’m pretty sure no one has ever called someone “sick” for liking well done cold emails.
  • His three reasons for preferring cold email are not particularly compelling, and #3 exhibits completely confusing punctuation choices.
  • The Anchorman meme? Totally irrelevant.
  • And of course: There is literally no reason in this email anywhere explaining why he thinks my colleague needs his services, or even any indication that he knows who she is. (She’s an ad specialist who never sends cold emails because she’s not a salesperson. It would only take a moment of research—and logic—to determine she’s completely the wrong audience for whatever it is he’s selling.)

This sender went on to send my colleague at least three more cold emails, each somehow worse than the first. One email is more or less just a meme with no CTA. I’ll go ahead and share some of my favorites below. Behold the terrible punctuation, sad formatting, and multiple cat memes. Or as the Colossus himself would put it, “Scroll Down for a Rad Experience!!!

3. The Zombie Outbreak

My colleague recently received this charmer apparently sent during a Walking Dead episode.

The problems:

  • While the subject line is catchy, this email gets way too into the gimmick. It’s a cold email to a professional, not a speech a youth pastor is giving to some really bored high-schoolers. Plus, part of the gimmick is that the salesperson assumes that if you’re not responding it’s not his fault. It’s important to have some humility about your work—especially when it’s not perfect.
  • The email doesn’t really offer any insight on the value the sender can give to my colleague or why he chose to reach out to my colleague in particular.
  • Additionally, the company he chose to mention in the beginning (the name of which I have blacked out) is the parent company of the company my colleague actually works for, clearly suggesting that the sender did little to no research on who my colleague is.
(Same, tbh.)

4. The Total Fiasco

This email is actually one in a series of emails (all of which I will share with you), and is so bad that a friend of mine from a different company independently forwarded this same email to me without knowing that I was already including it from my own inbox.

The problems:

  • Well first things first, let’s point out that this sender never writes a subject line. The only reason I actually ever clicked into her email in the first place is because I mistook her for someone else I work with.
  • Next up: the grammar/formatting. This is not an email your eyes want to read. The random all-caps words, the ellipses, the text-speak, the overuse of the word “massive”—it’s all terrible and actually leaves you confused about what she’s trying to say.
  • The whole first section of the email is just…bad. To make it totally clear what I’m seeing, I’ll rewrite it here and change her name: “My name is Raquel Smith and I run a company called Raquel Smith as well as [Social Media Company] where I teach others how to attract MASSIVE attention by using social media like a pro. You may have heard of me…or maybe not, but I found you (and your company) on LinkedIn.” I mean, is she actually running a company with her exact name or was this a botched cut-and-paste job? Is she representing Raquel Smith or [Social Media Company]? Why would she want to write a wishy-washy statement in which she says I may not have heard of her?
  • Besides not knowing which company she’s from, she doesn’t even make it clear that she knows who her recipient is. Any time she refers to the receiver’s company, she just says “your company.” There’s no indication that she knows where you work or has any idea why her services would be useful to you.
  • And to really hammer the point home, she finishes the email by letting you know she’s completely uncertain of whether she has the right person or not and that she’d prefer you to do the work for her by telling who she should talk to. And then she goes on to let you know that if the previously mentioned services aren’t right for you, don’t worry, she’s got others.
  • Finally, there is no CTA here. The closest she gets is to suggest you talk, which is cool, but it’s not a CTA, because it doesn’t specifically tell you how to connect.

Anyhow, enjoy a few more terrible emails from Raquel, including one that contains the phrase “I lied,” which is always comforting to hear from salespeople.

5. The ESL Email

My colleague forwarded this to me, mentioning that he felt bad for sending this to me because it’s clearly from someone whose second language is English, but he just had to pass it along because he received two of these at the same time from two different people. I don’t feel bad for including this email on this list, though, for a number of reasons.

The problems:

  • First, if you’re going to do business in a certain country, you should make sure that your salespeople are capable of sending impeccable emails in the language of that country. A company will not do business with you if you can’t speak the language, and an email (that can be easily checked by a translator if necessary) is a crucial time to demonstrate that capability. And while people are often willing to overlook odd phrasing when a language is your second language, punctuation and spelling are things anyone can and should have mastered. At the very least, spell your name right! This sender spelled her name differently in two different places.
  • Up next: Where does this person work? There’s no mention of her company, no links to a page that would help you research what items she offers, nothing.
  • While there is a clear CTA, she’s jumping waaaaaay down the funnel here. This is an introductory email, and rather than introducing herself, she asks for information to provide a quote. Not sketchy at all, right?

All of these cold emails are truly dreadful. To avoid joining their ranks, be sure that you’re sending out simple emails with clear CTAs, and that you’re doing your research on prospects before contacting them. Sales is a numbers game, sure, but it’s first and foremost a quality game.

Bonus #1: Lowlights from the Nutshell inboxes

I asked the Nutshell team if they had any terrible cold emails to share for this article, and they had some doozies. Here are a couple of my favorites, presented with their anonymous commentary.

The Crying Salesman

“After a couple of bland, forgettable contact attempts—work on that subject line, buddy—the sender of these emails began to unravel before my eyes.”

If the point of these emails was to make me feel bad for him, then mission accomplished. Unfortunately, I still have no interest in doing business with him or his company. Self-deprecating humor for the loss, actually.”

(For goodness sakes, man, pull yourself together.)

The Extortionist

This one totally infuriated me. First off, the guy tricked me into opening his email by invoking our CEO’s name in the subject line. (That ‘What time on Tuesday works best?’ line was also annoyingly presumptuous, considering we had never connected before and he didn’t know my availability.) And when I didn’t reply to him, he basically threatened to tell on me to my boss.”

“I considered writing back with, ‘I would never work with you in a million years, a**hole,’ but I’m going to be the bigger person and just ignore him forever.”

Bonus #2: The Worst Newsletter of All Time

This was forwarded to me by a colleague, and I couldn’t help but include it on this list.

My colleague did a fabulous job laying out the problems himself, so I’ll let him take it from here:

  • “The entire email is written in uptalk. (I’m assuming this from all the declarative sentences in this email ending in question marks).”
  • “Aside from the fact that it’s addressed to ‘marketing,’ the opening question: ‘We were wondering if you have a hard time keeping pace with XXXXX’s content…etc.?’ That’s not a question. It’s a poorly worded sentence, followed by a question mark. This is so ambiguously, unfortunately worded that I had to read it like six times. What does that even mean? Do they mean keeping up? Am I racing against XXXXX’s content somehow?”
  • “The ‘Yes?’ in italics. Is that supposed to be me responding? If so, why would I respond with a question mark? Is it because they’re just assuming (correctly) I couldn’t understand the first question? Also, the answer they were looking for was ‘No.’”
  • They liberally use bold and italics in a way that makes me want to scream.
  • “WHY FOR THE LOVE OF GOD ARE THE BUTTONS WRITTEN IN LOWERCASE? Zero percent of the rest of the email is written in lowercase. [I’m] assuming it’s because the logo is in lowercase. But on one of the buttons, the company name is the only word in title case.”
  • “They sign their name with a hashtag. If this email were a person, I would slap it.”
  • “They have three different CTA buttons.”
  • “The final CTA button reads ‘XXXXX seems #awesome! let’s go to a free trial’ Aside from the fact that ‘let’s go to a free trial’ is the longest way to say ‘Start a free trial,’ do not assume I think things are hashtag-awesome.”

I’ve never had a newsletter make me visibly shake before, but there’s a first time for everything.

Got any horrible cold emails rotting in your inbox? Forward the worst one to Your anonymity will be guaranteed.


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