Table of Contents

How to Stop Writing

Shitty Emails

Let's face it. Managers, directors, executives, or whoever owns the budget are tough to reach. It is almost second nature for them to ignore most sales emails because they get so many. Even this TopoHQ Study substantiates that only 24% of sales emails are opened. Add some truly shitty emails to the mix, and it is enough to drive the most patient marketing officers up the wall.

When emails cause the recipient to react with disbelief -- What were they thinking? Were they even thinking? -- it doesn't bode well for your prospective relationship. In fact, we don’t know whom to feel sorry for. Should it be for the person who spends time writing what he or she believes to be a spectacular email, or for the one on the receiving end?

In most cases, sales emails get ignored because they miss the mark with the prospect. On average, 71.54% to 84.78% of emails received in a day go into the trash folder as per this study by Mailchimp. Here’s the good news, though: you can prevent this.

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On average, 71.54% to 84.78% of emails received in a day go into the trash folder. Here’s the good news, though: you can prevent this. Get your copy of the Sales Email Guide.

Darryl Praill, VanillaSoft’s Chief Marketing Officer, Jason Bay, the man behind Blissful Prospecting and Jack Kosakowski of the Creation Agency , recently presented a webinar on “Shitty Emails! Are You A Repeat Offender?” In the webinar, they took real email examples and provided tips on how to make them better. They touched upon a lot of points that enable salespeople to create email pitches that people will read – and respond to.

Jason has devised a fail-safe way to help you get these sales emails right, complete with context and customization, which he presented during the discussion - the R-E-P-L-Y Method. However, before we dig into the details of the REPLY method, let’s take a look at a few bad emails the webinar participants roasted - examples that are mind-boggling at best and rage-inducing at worst. Shared miseries halve the pain and all that!


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When it Adds Zero Value




"We DO struggle with [insert pain point you solve for your clients]. Funny because it's true. How can I help you?"

- Your prospects after your reps roast a pain you solve for them. 

Comedy roasts see comedians deliver biting truth bombs, lasting no more than 15 seconds to elicit huge laughs. They're remembered & repeated by those who heard them. 

If your team could make your prospect laugh by highlighting a painful truth via cold outreach -- do you think it could start more conversations?

If you think so (or aren't convinced), I invite you to check out Virtual 1-paper, home to my CEO explainer & CEO testimonial video.

I can help onsite or remotely. Please get in touch to learn more.

This email doesn't make sense. It's evident that very little research went into this. Take the bracketed bit - insert pain point you solve for your clients - in the opening sentence for instance. Even though it is intended, adding this type of stuff can be confusing to the reader. If not written clearly, the recipient may think that the writer forgot to fill in the part or change the template or doesn’t care.

These inferences could be grossly wrong. The email writer might be a brilliant salesperson in person. However, once the person hit the 'Send' button, it was too late for damage control.

The sender is telling you to write funny emails and roast your prospects' pain points, but he doesn't tell you how and seems unsure by throwing questions at the recipient.

During the webinar, Jack points out that the writer doesn't deliver any value with this email -- instead, the reader is left to do all the work. You could have excused the poor writing if the author had a point beyond maddening vagueness.

For instance, let's take the below excerpts from the email. ‘Virtual 1-Pager’ doesn't tell the reader what it is, what to expect, or why they should click through to it.

“If you think so (or aren’t convinced), I invite you to check out Virtual 1-pager.”

If the prospect is not convinced by the end of an email, the odds of him clicking on another link (to get convinced) is less than zero and hence adds no value.

“Do you think it could start more conversations?”

You tell us, dude.

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If the prospect is not convinced by the end of an email, the odds of him clicking on another link (to get convinced) is less than zero and hence adds no value.

When it Appears Fishy



Important Letter for Jason

I wanted to send you a quick note, but I don't have your home address, so I put this letter online for you as a PDF.

Click her and take a look.

All the best,


P.S. This is just for you, it's very time-sensitive. Please don't share it with anyone else.

"Perform at a level that you didn't think was possible", -----

Wow! Jason must have felt 'important.' Or not. When we say brevity is essential when writing a sales email, this is not what we had in mind. And how creepy can it get? You cannot assume your prospect has enough time to sit around and read random PDFs when you wouldn't even give the gist of its content.   

Aside from the total lack of context and ominous tone, it is not clear what this person does or what pain points the writer is trying to solve. The writer might have been going for a clickbait effect, but he or she could only make it came across as a phishing email.

The email looks quite shady, and the recipient is likely to send it to the spam folder. Marketing officers are especially wary of such scam-like emails, however harmless they might be. The fear of security threats on their device will take precedence over potential value-proposition. So, drop the suspense and say it as it is.

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If the prospect is not convinced by the end of an email, the odds of him clicking on another link (to get convinced) is less than zero and hence adds no value. Get more sales email tips in the How to Stop Writing Shitty Emails Guide.

When it is Full of Assumptions



Checking In

Hi Darryl,

I know you would see tremendous success on [company name]! Our goal is to help you reach your business goals, as we're able to identify customers at the lowest possible acquisition price and drive more users down the funnel towards purchases.

Please let me know when you're available this week for a quick chat - and if this is something you are not interested in at this time please let me know as well.

Looking forward to hearing from you.

Oh, we're off to a presumptuous start! This person offers to help Darryl achieve his business goals. What are these business goals the sender intends to solve and how? Even if words like 'lowest acquisition price' and 'more users down the funnel' do get the reader's attention, the sender doesn't say how or why he believes Darryl might need it. A dash of empathy concerning the reader's actual (well-researched) pain-points could have made all the difference.

On top of that, the onus of scheduling a chat/meeting is also on the recipient. Does it still surprise you when the likes of VPs and CMOs are sick of unsolicited and meatless emails from lazy salespeople?

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Don't make assumptions in your #prospecting emails. A dash of empathy concerning the reader's actual (well-researched) pain-points can make all the difference. Get the Sales Email Guide.

When it is More About YOU
Than the Prospect



Lead Generation Program

Hi Darryl,

I hope you are doing great, I just called and left you a message. I wanted to re-introduce [company name] and have the opportunity to tell you all the new things and improvements we have done throughout these years.

About us:
We have been 12 years in business, our expertise is in demand generation for a bounty of categories including ERP, Telecom, Marketing Automation, AI & Security. We specialize in Content Syndication campaigns as well as HQL, MQL, Demos and Appointment Settings, just to name some.

If you have any availability, I would like to discuss with you about the services that we offer and on how we could help you and your company generate more potential clients. 

Thank you for your time and I look forward to hear from you soon.

We do feel for the salespeople who write crappy emails. They didn’t mean to send something that went straight to the trash folder. They were hoping for a response, and they really believe they had done their homework, taking care to include prominent keywords (MQL, Marketing, AI).

Nobody writes anticipating a rejection. And yet, it happens all the time. 

During the webinar, Jack Kosakowski said that he doesn't think this email is beyond redemption, though. He believes removing the 'I, We and Me' and adding more 'You-s,' that is, making it more about the recipient can still save the copy from being an utter disaster.

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Are your #salesemails all about YOU? Try replacing the "I, We, and Me" with more "You-s" to make it more about the recipient. Get the Sales Email Guide.

When it is Too Brief



Ideas for VanillaSoft

I had a few ideas to generate customer interest in your Sales Funnel Software services at

May I send further details?

That was meatless succinctness at its best. Yes, Chief Marketing Officers are busy people, and the sender has been considerate enough to keep it short. The writer just forgot to mention who he or she is and his or her company name. An ideal email contains 50-125 words as per this Boomerang analysis.  

‘May I send further details?’ If you have further details, don’t ask and wait for a reply to send it. Just send it. Oh, and Darryl doesn't do Sales Funnel Software Services. Zero marks on research and interpretation of Darryl's LinkedIn profile.

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If you have further details, don’t ask and wait for a reply to send it. Just send it in your first email.Get more #salestips in the Sales Email Guide.

When it Makes the Reader
Do All the Research




I am working with a renowned Asian-based IT company that is engaged in providing a long chain of mobile application development services. We have developed a number of effective mobile apps for several major industries such as IT, Fashion, Fintech etc. With over 8 years of experience, we have maintained a broad customer base globally. Please click here to know what we can offer you to help with the right solution regarding your mobile app needs ---

Waiting for your valuable response,

The wait won’t be over anytime soon. This email doesn’t convey anything. The recipient has to look up the company and the services they offer. There is no clue as to how they came to the conclusion that the prospect has mobile app requirements. Again, it is the prospect who has to spend his or her valuable time researching the kind of mobile apps the sender’s company has delivered and how it aligns with the recipient’s business goals.

It doesn’t look like the writer is even aware of the prospect’s industry domain, rather he or she is just shooting in the dark. They talk about global clients and eight years of experience but offer nothing that sheds light on the customer base or the kind of work they have been doing. This email only tells one thing - that they are all talk.

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Don't make prospects spend their valuable time researching your company to learn what you do. If the prospect has to research you to decode your email, you've already lost.

When it is Full of Empty Words




I will do my best to keep this compilation short and to the point for I can only imaging the demands on your time in your myriad pursuits. I am an executive recruiter gent here at ----- and we're in the midst of a quest to find a Global SVP Brand Creative for our growing team.

Given this, I thought to reach out to you if you might know of someone who might have furrowed brow of intrigue relative to this key imagination-laden seat-of-import.

I could type/phone more if need be as in my stead to leave a revered source fallow would cause me to lose a strong measure of REM sleep.

Take care and happy holiday season to you down/out there.


Fast food contains thousands of calories but doesn’t exactly nourish your body. Similarly, filling an email with too many phrases, jargon, and filler sentences may fill the page but seldom carry any weight. Talk about a bunch of words being just that – a bunch of words. When there is no context, personalization, or even a positive reflection on the brand you represent, the recipient will hit delete.

We understand it is painful for you to remove words from an email you agonized over for a good two hours. However, if a word doesn't add value to the conversation, there is no reason for it to be there. 

True for an email, true for a couplet, true for a whitepaper, and true for everything else.

Read every word aloud. Check if each word pulls its fair share of the weight. If you were to remove that adjective, would the email crumble? This exercise might save your email from being another example of a shitty email.

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If a word doesn't add value to the conversation, there's no reason for it to be in your email. Get the Sales Email Guide now!

The REPLY Method

Now let's come back to the R-E-P-L-Y Method, mentioned earlier, to learn how you can prevent shitty emails in your sales outreach. 

You may have heard the phrase, "Don't sweat the small stuff." An email might look small but remember that often the little details can lead to the most significant wins. Sweat it when it comes to email. Emails need to be more direct and 'to the point' in their style, mainly because people who read are often skimming.


Often, salespeople struggle to begin an email; it's a challenge filled with plenty of time, backspaces, and frustration thrown in. Building templates using the REPLY method can alleviate much of the pain of writing sales emails. Using templates and continuously fine-tuning them can drastically improve your game.

This kind of semi-automated approach is about effortlessly addressing your prospect's pain points in a contextual and personalized manner. Here is a sample email that followed the REPLY Method to the T. 

shitty emails-ResultExamples

R - Results

A results-centric statement hooks the prospect right away, especially if it is a number/solution that can impact their business. Supplement that statement with how your solution will achieve the result (see example), and you have the Result part down pat.

Often, salespeople's excitement about their product blinds them to the fact that the prospect has no idea what they're talking about. Trust us; no prospect has so little to do that he or she is happy to entertain random emails that offer no substantial result.

Vague claims are plain annoying. Period. Let your email unravel the answer to your prospect's first question, 'what's in it for me?,' in the first couple of sentences. In other words, you're baiting them to read on to the call-to-action.


E - Empathy

Being empathetic to the prospect's cause involves addressing specific challenges this recipient faces and deliverables he or she requires. Most prospects receive generic messages and 'invitations to connect' every 20 minutes. They hit delete/spam buttons faster than you can say 'wait.' 

Senders often forget that there is a human behind every screen. Writing a compelling sales email requires you to weave together insights gained through phone calls and research to create a message that resonates with the reader. Never forget that a sales email is about your prospect, not you the salesperson.

In the R-E-P-L-Y example above, the sender is aware of how disappointing it can be if the video doesn't work after all the time and effort put into it. It is even likely that the recipient's company failed in its video marketing efforts in the past. In one strike, the sender is acknowledging the pain of video-making while offering a solution.


P - Personalization

 Salespeople are often under tremendous pressure to 'finish the lead list within two days or a week.' After a point, they may push out emails without caring about the content. That's bad, and the results will reflect that lack of care. Personalizing your emails can save you much effort and secure more leads.

Don't you love it when somebody addresses you personally - 'Hi ABC' as opposed to a plain 'Hello'? However, personalization has become much more than the use of the first name over the years. Your emails must demonstrate that you understand specific, personal pain points and should offer solutions that are relevant to the recipient.  

'He or she understands where I am coming from and makes a compelling point.'

'I feel like a human and not some random email ID on this person's list.'

You make a prospect feel like a person rather than a target on your contact list, and you will be much more likely to get at least one reply or call back.


L - Laser Focus

Prospects are usually busy bees. Even if they're not, they may have other tasks that they'd prefer to tackle than reading 'shitty' emails. Attempt to keep your emails to no more than four to six sentences (approximately 125 words). Said another way, your message should fit within the screen of a standard smartphone without having to scroll. Let every sentence be a critical hit – results, empathy, and personalization -- so that your contact might at least read and remember rather than skim and forget.

Most importantly, please don't forget to be specific when you request an appointment to take the conversation further.


Y - You

Ever had an experience with a date who seemed interested in talking only about him-or-herself? Or that colleague who talks over everyone? Such I-me-myself communications and self-centered emails never warm the prospect to the sender.  

'I would love to talk to you about this.'

'We have this awesome idea that can solve the global climate crisis.'

'I'm reaching out to introduce myself and see if we can have a 10-minute chat about the product this week.’

Can you spot the remotest interest in prospects or their pain points in lines like these?

Like Jack says, start with removing the I's and We's as much as possible. Take a cue from the R-E-P-L-Y sample email from the beginning of this section; make your content about the recipient and not about the sender. Ensure your emails build trust and pave the road to a long-term relationship.

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Emails need to be more direct and 'to the point' in their style, mainly because people who read them are often skimming. Learn about the REPLY method to get better results.

Summing it All Up with a Bonus Tip



To ensure that you bypass the 'instant-delete' reaction reserved for shitty emails, having a few REPLY templates handy would be a good start.

All set to step up to the REPLY plate and send a better email? Your prospects will appreciate some clarity and brevity, and you will probably get a better response when your communication looks sharp. Simply say what you want the reader to know about you and what's in it for the prospect. Show that you understand their plight. Write your emails, so they are one-on-one, and keep your message brief and focused on the prospect, rather than yourself. The results will speak for themselves.

Want to hear more about how to improve your emails?

We've all gotten those really bad emails...and we've all been the one to send them at times. Well, it's time we talk about how to do them right. However, to do things right, you need to have a very clear understanding of doing things wrong.

Darryl Praill was joined by Jack Kosakowski and Jason Bay to talk through some real-life email fails and how to improve them. 

Watch this video and learn how to: 

  • Understand what messaging decision makers respond to.
  • Accurately cater the benefits of your solution to prospects.
  • Avoid sending sloppy and ineffective outreach.
  • Spur meaningful conversations consistently.

Get Started Now!

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J Telecommunications

Jody Weinberg J Telecommunications

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