by Karan Sharma

Are you wondering why the average open and response rates to your email campaigns are low? A while back I wrote a blog post about the importance of copy in the outbound lead generation and how to do it right. Now, to help you better understand why your emails are not converting, I’ve handpicked some of my “favorite” email failures and explained why they’re marked as SPAM by Google or/ and by prospects themselves.

Briefly put, here are 6 real-life examples that show what not to do in your next email campaign. I’ve numbered the mistakes in each example so that they are easier to follow in the explanatory paragraph below each screenshot.

1. Email subject line

Using an exclamation mark in the subject line is a clear spam signal. It sounds as if you were shouting at the prospect and force him to take a certain action. The same applies to exclamation marks used in the email text itself. If, for example, you really want to wish someone “happy birthday” it’s just best to ring them up instead of using exclamation marks.

2. Email address

The email address is a generic one. My advice is to always try to find a person to address because you address the specific needs and challenges of someone. Writing to a generic email address will somehow force you to write in a very broad, impersonal way and lose the prospect from the very start.

3. Addressing the prospect

It’s best to always write the name of the person you’re contacting and be polite. “Hey” is a very friendly “hello”, too friendly to be addressed to a person you’ve never met before. It’s definitely not a sign of respect. Being friendly with friends is one thing, being friendly with strangers – especially high-level executives – is just weird.

4. The first sentence

Here is where you should be creating a personal connection by telling the prospect how you’ve found them and why you’re emailing them. In the example above, the email writer failed to create a personal connection – the beginning is very salesy and doesn’t trigger trust from the side of the receiver. There is no point of reference and no connection is built with the prospect.

Furthermore, never say “I hope you’re doing well” to a stranger. Nobody does that. You already wasted the prospect’s time with that sentence because he doesn’t know what you’re talking about.

In this email, the prospect probably feels lost completely right after the first paragraph. The person sending the email speaks about a solution that allows him to engage global customers in just 5 seconds. First of all, he should have introduced himself/ herself, explain why they’re reaching out, how they found the prospect, etc. The text is very salesy and focuses only on the solution, not at all on the prospect’s problems and challenges

5. Bolding text

Normally, you don’t put anything in bold but when you do, just bold only one thing so that the focus goes on that word/ phrase. In the case of this email, bolding makes the text too in your face and too salesy. Bolding several elements in an email text is a clear sign of spam.

6. Different font size

This makes the email look messy and written in a hurry. It sounds like a “how to setup” guide when in fact the sender doesn’t let the prospect set up anything now. He just wants to close the deal with a single email.

7. Listing

The sender is doing many different things (bolding, listing, etc). He/ she tries to sell the product from the first sentence, lists the benefits, and then lists the benefits again and tries to sell it again. After reading this email, the prospect expects for the call to go in the same direction – listing benefits without understanding his needs.

8. Closing paragraph

By this time, the prospect should know who you are, how you’ve found them and why you’re mailing them. In this case, the sender failed to achieve this. The text is too colloquial, it sounds impolite and too much like spoken English.

In the closing paragraph, you should also make it clear that you want a call to understand their process better so you can determine whether there’s a fit. Never ask the prospect to determine whether there’s a fit based on the info in the email. They won’t have time for this.

“Thanks in advance” – this makes the reader feel angry. It’s like forcing someone to do something for you in a manipulative way. Thanking someone in advance is like trying to make someone feel guilty if he doesn’t take the action you’d want them to. “Thanks in advance” backfires so make sure you never use this in your emails.

9. Signature

An email coming in from a Business Development Manager is already a trigger in people’s minds that this is spam because most spam messages are from BDMs. Usually, prospects reply to emails that come from the Head of something. They don’t reply to emails from BDMs.

1. Addressing the right person

If you can’t find the prospect’s email address and you choose to send an email at hello@, at least make sure you are addressing the right person. In this case, for example, it was the wrong person. Furthermore, the sender has no idea about the person he’s mailing. He asks to be directed to whoever is responsible for Testing/ QA when in fact that person is Fabrizio himself. So this email is not bad because of the content alone but also because there was no research done prior to writing it.

2. First sentence

The sender failed to establish a point of reference and build trust from the very start. What if the email doesn’t find him well?Bottom line, this type of content is just filler content. The problem is that it doesn’t explain anything, it doesn’t take the prospect further into the process and it can even make him angry. What you should do is go directly to the main point because you respect people’s time, not want to make them read things that only sound polite.

3. Main content

Again, bolding too much text is very salesy and looks spammy.

Never use sentences like “we have the most professional and experienced testers”. That’s a lie and the prospect knows it. You don’t want to sound like those cheesy and salesy TV commercials.

Stick to the point and don’t add words that don’t mean anything. In this case, what does “Independent software testing company” mean? Are there also dependent ones? Random words are a waste of your prospect’s time.

Avoid listing things because it is a spam signal for the reader. Also, make sure your grammar and spelling are not messed up so that the content follows a natural flow.

4. Closing paragraph

In this case, it’s not personal enough. By this time the prospect should have known what’s in it for them so the “if” is not necessary anymore. He should have understood the value. Again, the exclamation mark after the word “soon” sounds pushy and disrespectful. The idea is not to force the prospect to have a call with you but to suggest a call so that you understand their needs better and establish whether there’s a fit.

5. Post Scriptum (P.S.)

Don’t use P.S. because it’s trendy and doesn’t use it before finishing an email.

Always stay away from phrases like “Thanks for your help.” They suggest indirect manipulation. You’re already thanking your prospect for an action that they haven’t yet taken, thus forcing them to feel as if they owe you that action. Be straightforward and honest about your intentions and you will reap the benefits.

6. Opt-out option

This is a clear spam signal and it tells the prospect that he’s just read a mass email. He won’t reply after this.

1. Email text

By starting the email directly without introducing himself, the sender failed to establish a personal connection and to build trust. Furthermore, he is not upfront about the why and the how. How did they find the prospect and why are they targeting them?

Apart from being badly organized and very salesy, the text is very long and hard to follow until the end. Nobody has the time to structure the info and read the whole of it. It’s like rambling on a topic.

Moreover, the sender lists the price in the email. Never do this. It is too eager and too pushy. Basically, it looks as if you’re trying to close a sale with one email.

2. Introducing trial accounts in emails

This is a clear signal that the sender has completely failed to make the text about the prospect and to point out how the tool can solve the prospect’s challenges. Bad English grammar and spelling make the text very hard to read.

3. Email and password

First of all, has the prospect asked for a free trial? If no, then don’t impose them on them.

4 and 5. Closing paragraph

The paragraph is filled with grammar mistakes and it sounds very impolite. The CTA is usually that last sentence where you’re kindly asking your prospects for a few minutes of their time. Why do you want a call? To understand their process better so you can determine whether there’s a fit.

In this context, the word “soon” is very pushy.

The intro paragraph is more or less ok. The only thing that can be deterring for prospects is the mentioning of the word “Ukrainian” because they can see it as being too far, not English proficient, etc. I would leave the country out if it doesn’t add a plus value to the intro text. Remember that this is where you capture the prospect’s attention and build a personal connection. Every word that you use needs to fit this goal.

Also, while giving a link to your most relevant projects might work, including one with company photos is a bad idea – it feels as if the sender wants to push things on the prospect and that’s highly deterring.

1 and 2. The email body

After the okay intro, it’s a pity the sender jumps directly to pricing schemes. This is much too soon. As a matter of fact, prices should not be discussed in initial emails at all unless asked for by the prospect as part of the qualification. Trust should be established now. The aim of this email should be to get a call or a meeting to understand the prospect’s process better so you can determine whether there’s a fit.

Why are they sending 5 PDFs? Because they want to make the sale with a first email. The sender wants the prospect to decide whether they are a fit or not by giving him the whole information that they would normally give during the entire sales process. That’s a big problem because nobody has the time to go through 5 PDFs, a list of projects and company photos without even understanding what’s in it for them.

Furthermore, in the example above, you will see that the text is filled with grammar and spelling mistakes. Mistakes in sales emails denote a lack of professionalism and even a lack of respect for those reading them.

3. Benefits list

In the example, you have seen a list of benefits for the prospect. The only problem is that they are just filler content. Why? Because benefits should not be general ones but should address the prospect’s main needs and challenges. Moreover, a 3-day free trial is useless with a developer. A developer becomes useful in month number 2. If the prospect knows this, he will surely feel tricked at this point. Besides this, all the information is irrelevant because the email was sent to a CEO, not a CTO – a person who is qualified to assess all the things presented here.

4. Ending

“Awaiting your answer, thanks.” Besides being unprofessional, the ending is pushy and not at all action-triggering.

1. Subject line

The use of capitalized words in the subject line is a clear spam signal and it feels like shouting at the prospect. Avoid doing this at all costs.

2. Addressing the prospect

Always use the person’s full name or his first name. In this case, “Dear Mr. Karan S.” makes me think that, not only am I being spammed, they don’t even know my full name. This is enough to make me stop reading and never come back to this email.

3. Starting the email

By starting the email with “nice to present you some advantages of….,” the sender makes it all about them and not about the prospect’s needs from the very beginning. In this case, they failed to be upfront about “why” and “how”: how have you found me and why are you emailing me? Without this information, I, as a prospect, can’t understand why I’m supposed to continue reading anything.

4. Bolded text in lists

Yes, not only is the text bolded and written with a different font, it’s also organized into a list! At this point, there’s already too much information that is hard to place in a context. The sender hasn’t yet determined if there’s a fit and they’re already stuffing the prospect with detailed info that he’ll most likely make nothing of.

5 and 6. Email body

Different font and style after the reader have just got used to the initial formatting. This can only contribute to more confusion. Furthermore, make sure to never use red since it’s highly pushy and associated with mistakes, or something that needs to be corrected – many teachers still use red when evaluating students’ homework.

The impression at this point is that this salesperson has no idea what he’s doing. He probably copy-pasted some stuff from different PPTs and pasted the info in the email. Instead of finding out more info about the prospect, he gives him loads of information so that he can qualify them. Prospects don’t have that time! And if they do, why should they invest it here?

7 and 8. Final paragraph

This email came from a company that lets you set up a subsidiary in Hong Kong. After having read a text filled with spelling mistakes, now the prospect is being asked to hand over his passport details. Crazy, right? At this point, the prospect doesn’t even know what this company’s business model is, why they are targeting them and what their benefit is. Of course, nobody will give passport details in this context. It’s much too early for that!

The CTA is missing. The CTA is usually that last sentence where you’re kindly asking your prospects for a few minutes of their time. Why do you want a call? To understand their process better so you can determine whether there’s a fit.

1. Subject line

The subject line is incoherent for the content of the email, it has nothing to do with the content or with what the sender is about to offer – an eBook.

2. First paragraph

The sender completely failed to establish a personal connection, they didn’t tell the prospect who they are, how they found them and why they are emailing them. “If I don’t know who you are and what’s in it for me, I won’t check any material you may send my way.” That’s how your prospects think.

3. Links in email

When there are too many links in the email text, it’s likely that some of the emails you send will directly get into the spam folder.

4. Using mass email services

In this case, when the email comes from Yesware it’s hard not to consider it spam.

According to the CAN-Spam act and its EU counterparts, the sender is supposed to provide their company’s physical address in the email. In Germany, they also need to provide their company’s registration number.

Briefly put, here’s a very useful list of things that we’ve discussed while analyzing the examples above and that you should take into account at all times:

In the email subject line:

• Never capitalize entire words
• Never use exclamation marks

When you address the prospect:

• Make sure you’re addressing the right person – double check the email address
• Always use the person’s full name or his first name

In the first paragraph:

• Create a personal connection by telling the prospect how you’ve found them and why you’re emailing them
• Never say “I hope you’re doing well” in the first sentence unless that person is your friend.

In the email text:

• Don’t be salesy and try to close the deal from the first email.
• Don’t bold text or change font style/ size – it makes the text look messy.
• Avoid listing benefits/ features/ options, etc.
• Stick to the point and don’t add words that don’t mean anything
• Triple check for spelling and grammar mistakes
• Don’t overload your prospect with tons of info
• Make it about them, not about you

In the final paragraph:

• Never be manipulating by thanking your prospect in advance. It will backfire.
• Use a CTA, usually that last sentence where you’re kindly asking your prospects for a few minutes of their time. Why do you want a call? To understand their process better so you can determine whether there’s a fit.
• Don’t send emails from a Business Development Manager’s account.

That being said, remember that your salesperson is your strongest brand representative. If he/she is not professional you can put a lot of money into branding everything and still lose at the moment of the sale. Also, people talk to another people and share their experiences. If one person receives a poorly written email or a pushy call from your company representative they will tell others about it. That’s the problem of having a low-level salesperson emailing people from all over the world.