The 7 Facepalm-Inducing Sales Email Approaches To Avoid

My first job after graduating was as a salesperson for Groupon. I learned a lot and credit the training I received as essential for setting out on my own and growing my company.

With experience on both sides—as the salesperson pitching the brand they represent and the prospect receiving pitches from other brands—I have a lot to say about what makes an effective (or ineffective) pitch.

Here are actual sales pitches I've received, why they'll never work and what to do instead.

1. Your Approach Is Blatantly Disingenuous

Here's what they did wrong:

They get a few points for mentioning clients featured prominently on The Blogsmith's website—but they should've stopped there.

The claim "my team spent a few days preparing a personalized sales strategy" is a blatant lie. Spending hours or days on a first touch with a cold pitch is simply not a scalable approach.

And if they truly had spent any time doing that (not recommended), they should've sent a sneak peek or teaser, at minimum, to encourage setting a call.

Pitches such as these read like an attempt at creating disingenuous reciprocity.

It's like they're trying to make the recipient think they owe them for the time they supposedly spent on creating a custom strategy that was never asked for or agreed to in the first place. They're putting the cart before the horse in an attempt to corner the recipient into a meeting.

What to do instead:
Never make empty promises—they will come back to bite you when people either ignore your sales email or use it as a terrible example of sales outreach in a Newsweek article.

When I'm feeling especially cheeky, I challenge them to show proof for claims that I know are blatant lies. And unsurprisingly, I've yet to receive a satisfying answer that defies the terrible first impression they started with.

In fact, that's exactly what happened when this next salesperson reached out, claiming that one of their clients was familiar with my brand. I asked, "Which client?" and was asked to schedule a call to get the answer—no thanks!

2. Your Pitch Lacks Effective Personalization

Here's what they did wrong:

The "custom" video pitch has been rising in popularity. As with the aforementioned example, the issue lies in its disingenuousness.

The salesperson claims they made this video just for me, but we all know the only part that's truly custom about it is they mention my name and my company's name.

And sure, they went out of their way to showcase a visual of them scrolling through my website and socials to the tune of a prerecorded standard pitch—very thoughtful.

What to do instead:

If you want to cut through the noise of the dozens of sales pitches the average small business owner gets in a week, personalization is a must.

To do that, start with a pitch template and customize it without overthinking it. You can adjust it to:

• Share names of businesses you've worked with that are relevant/familiar to the specific prospect.
• Share relevant work samples or client results.
• Comment on a recent mention of the brand in the media to demonstrate that you've done some research.

But be warned: failed personalization as a first impression is terribly hard to overcome.

I've received emails that didn't replace template fields (e.g., [Add brand name here]) or were straight-up copies of emails sent to other brands (complete with another brand's name listed instead of mine).

In the end, the only message I got was that the salesperson—and the brand they represent—aren't careful.

3. You Make the Recipient Do the Work To Judge if There's a Fit

Here's what they did wrong:

It's your job as the salesperson to help your prospect understand the relevance of your outreach. So, seeing this salesperson ask their prospect to specify the type of work samples they should send over is rather puzzling.

Nothing in this email helps me decipher whether they're a good fit for me (spoiler: they aren't), so I ended up moving it out of my inbox and into my "Annoying Emails" folder for future chuckles (and content).

What to do instead:
Prospects can distinguish between "personalized" templates that make it seem like you're the best fit for them and a genuine, thoughtful, custom outreach attempt.

If you don't have enough information about your prospects to give them compelling reasons to work together, consider starting with a different kind of email instead. For instance, provide a rundown of your value proposition with a standard approach and invest more time in personalization for the follow-up email.

Avoid donning your emails with red flags by having an idea of your brand's ideal use cases. Spend a little time qualifying leads before reaching out instead of spamming pitches to random contacts. Outreach without purpose isn't sales—it's a waste of everyone's time.

Bonus tip: As a general note, each sales email should have a single clear call-to-action that's easy to act on.

4. You Rely on Automation Without a Human Touch

Here's what they did wrong:

Timing is everything. The fact that this person asked—on Sunday at 4:06 AM local time—if I had seen the first message she sent—on Friday after the close of business (during the week of the 4th of July, no less)—resulted in a double take.

I suspect she didn't intend for these messages to be delivered at such inopportune times but instead used some kind of LinkedIn automation tool for prospecting.

That's a prime example of why shortcuts aren't a good idea for building relationships: She ruined her chance to make a sale from her very first message and only reinforced that further with her follow-up messages.

What to do instead:

First and foremost, she needs to reassess her use of automation.

Second, it's okay to make some assumptions about your prospect, especially in terms of getting to the point of why you're reaching out.

But it would've been more effective for her to start her outreach with a conversation that would result in me replying with an easy "yes" (or "no" to quickly disqualify me and not waste her time further). For example, "Have you ever considered selling your business?"

Based on my answer, she would understand if it's worth sharing more details or asking more questions. After some back-and-forth engagement, I would likely be more invested in moving the conversation forward.

5. You Sent a Service List, Not a Pitch

Here's what they did wrong:

I'm sure you've gotten dozens of emails like this. It's a generic list of services, not a sales pitch (with several spelling errors, to boot).

What to do instead:
There's nothing in the email I can use to decide whether I want to work with this person or brand. In fact, I have no idea who they are or who they represent. It's clearly a mass send and a very ineffective one that lacks personalization.

Coming from a content creation perspective, the inconsistent casing for each list item gives major red flags. And I have no idea why "SEO Discount offer" is in quotes.

Looking at these things may seem nitpicky. But to me, someone who doesn't put effort into something as small as copyediting their emails isn't bound to put effort into anything, let alone the services they provide.

Presentation plays a significant role in building trust. And it's always the small things that come together and make you truly appear professional.

Bonus tip: Instead of using a random @gmail.com email address, as this salesperson did, use a company email or professionally branded social account to send your pitch.

6. You Treat the Recipient Like They're Your Personal Secretary

Here's what they did wrong:

This is another example where either automation or laziness is at fault. This attempt is especially cringeworthy because my email address starts with my name. So they're basically emailing me to ask me to forward this sales pitch to... myself.

Beyond this obvious faux pas, I resent the nature of the ask if it was intentional. I am the founder of my company, not their personal secretary.

The fact that he made an incorrect assumption instead of treating me like the decision-maker I am effectively flagged this pitch as dead on arrival.

What to do instead:

Let's say that this salesperson had correctly assumed that I'm a gatekeeper for the decision-maker they hoped to meet—what have they said to convince me to help?

When it comes to sales success, with every touch, you've got to be able to answer the question, "What's in it for me?" on behalf of the prospect.

Every once in a while, I respond to especially bad email pitches for fun—here was my response to this one:

I never got a response. Shocking, right?

7. You Display an Astonishing Lack of Confidence

Here's what they did wrong:

There are so many issues with this pitch email, but the main one I want to call out is the very first line: "Hey, super sorry for the cold email."

Me too.

What to do instead:

Don't waste the prospect's time. If you're not confident that your offer is a good fit for the recipient, don't send the email. The lack of confidence is a complete turnoff and isn't going to get any responses anyway.

Step Up Your Sales Email Game

An effective sales pitch isn't cold and robotic—it demonstrates empathy and understanding.

While most salespeople are in part motivated by minimum sales activity numbers they must achieve to keep their jobs, the best reward for a job well done is increasing your earnings with commissions on closed won deals.

The most effective path to becoming a highly paid salesperson is to create a pitching strategy that involves the least wasted time and effort by all involved instead of spamming every contact you come across.

About the Author

Maddy Osman is the author of "Writing for Humans and Robots: The New Rules of Content Style". Maddy's journey from freelance writer to founder and CEO of The Blogsmith yielded numerous insights to share about content creation for enterprise B2B technology brands. Her efforts earned her a spot in BuzzSumo's and Semrush's Top 100 Content Marketers and The Write Life's 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.