When Bad Sales Emails Miss the Mark: Lessons from the Inbox

Sales emails are one of the most powerful tools in a professional’s arsenal, but only when they’re done well. Unfortunately, my inbox has become a case study for how not to write a sales email. Instead of sparking interest or creating opportunities, these emails fall flat due to poor personalization, lack of effort, or simply missing the mark entirely.

In this article, I’ll break down three examples of bad sales emails I’ve recently received, highlighting the mistakes and sharing actionable takeaways for crafting better outreach.

Email 1: The Fan Who Isn’t a Fan

Subject Line: Let’s Meet

This email starts with a bold opening:

At first glance, it seems complimentary, but let’s unpack the issues:

1. An Empty Compliment:
   If someone claims to be a fan of your business, they should back it up with specifics. Which product? Which initiative? Instead, this email is vague, and the praise feels like a generic opening line used across dozens of cold emails. Authenticity matters and this didn’t have it.
2. A Critique Without Context:
   "Your products need to be revamped on Amazon."
   Offering unsolicited feedback is tricky, and this example misses the mark entirely. The sender makes a bold claim but provides no details, examples, or evidence to support it. This approach can feel insulting rather than helpful. Constructive feedback should always be tied to actionable insights.
3. The “I Made You a Video” Gambit:
   “I made a video for you. Would you be the right person to send it to?”
   This line is both outdated and disingenuous. If they’d genuinely made a video, it would have been included in the email. Instead, it’s a tired tactic designed to pique curiosity and one that no longer works in today’s sales landscape.

Lesson: Flattery without substance, vague critiques, and overused tactics do more harm than good. Sales emails should be specific, personalized, and value-driven.

Email 2: The Tactical Misstep

Subject Line: 11 Tactical Hat

This email got my attention for all the wrong reasons. It opened with:

Let’s dive into the problems here:

1. Getting the Product Wrong:
   It’s 5.11 Tactical Hat, not “11.” A quick visit to our website would’ve made that clear. Getting basic details wrong shows a lack of research and undermines credibility.
2. Name-Dropping Without Context:
   "13K merchants, including Tom Ford, use [our product]."
   Dropping a high-profile name like Tom Ford might seem impressive, but it feels out of place when there’s no context tying it back to my business. How does this relate to my needs or challenges? Instead of name-dropping, focus on how your solution is relevant to the recipient.
3. Misplaced Humor:
   “Fun fact: I came in last in my third-grade spelling bee.”
   Humor can be a powerful tool in sales, but only when it’s relevant and well-timed. In this case, the quirky line feels random and out of sync with the rest of the email.

Lesson: Get the details right, tie any credibility-building references back to the recipient, and use humor sparingly and only when it adds value.

Email 3: The Generic Inquiry

Subject Line: State – John

This one takes the prize for being both lazy and irrelevant:

Here’s why this email failed to make an impact:

1. Lack of Research:
   Asking an ecommerce brand if they ship outside their home state feels almost comical. Nearly every ecommerce business ships beyond state lines...it’s the default expectation. This question shows zero understanding of the business or its operations.
2. Surface-Level Personalization:
   While the email uses my name, state, and a reference to Shopify, that’s where the personalization ends. This information is easily pulled from a lead list and doesn’t demonstrate any deeper knowledge about my business or its specific needs.
3. No Clear Purpose:
   Short emails are fine, but they need to have a point. A vague question with no real value or follow-up insight is a wasted opportunity.

Lesson: Personalization goes beyond filling in variables, and emails should have a clear purpose that offers value or sparks a meaningful conversation.

How to Avoid These Sales Email Fails

What these emails have in common is a lack of effort. Sales professionals often fall into the trap of prioritizing volume over quality, but it’s clear that taking the time to craft a thoughtful, relevant email is far more effective.

Here are five tips for writing sales emails that work:

1. Do Your Homework:
   Research the recipient’s business, challenges, and industry before hitting send. A well-researched email immediately sets you apart.
2. Get the Details Right:
   Double-check product names, company information, and any references to avoid embarrassing mistakes.
3. Personalize with Purpose:
   Reference specifics about the recipient’s business, not just generic information. Personalization should show that you understand their needs, not just their name and location.
4. Bring Value First:
   Instead of opening with a critique or vague promise, offer actionable insights, examples, or solutions that could genuinely help the recipient.
5. Be Clear and Concise:
   Don’t leave the recipient guessing why you’re emailing them. Make your purpose obvious and focus on starting a real conversation.

Final Thoughts

Sales emails aren’t just about getting someone’s attention, they’re about building a relationship. A poorly crafted email wastes the sender’s time, the recipient’s patience, and the opportunity to make a meaningful connection.