The 5 Deadly Mistakes of Sales Prospecting Emails

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Contrary to what most people believe, prospecting is not a numbers game. You don’t have to send 100 emails just to hear from one or two of them. You know the numbers are true if you’ve been conducting cold or warm outreach for a while.

In fact, some people boast a response rate of 20%. While I can’t give you a specific number for my cold email response rates, I can tell you I’m sending cold emails -- a lot.

I also receive a lot, so I’ve identified the lethal cold emailing mistakes I see most often. Avoid these cold emailing mistakes, boost your response rate, and land more clients. Whether you’re sending a sales pitch, a guest post, or asking for a quote -- these mistakes can kill your productivity and your chances.

If you have no idea how to write a sales pitch, no problem. I’ve got some templates for you too.

Mistake 1: Missing the decision maker

Your cold emailing campaign will hit a wall if it’s sent to the wrong person.

If you’re lucky, someone will forward it to the right person. But even in this case, you’ll miss the opportunity to personalize your email content and establish a connection with the receiver.

A common lazy salesperson’s practice is asking an employee at a prospective company to send you the contact information of the key decision-maker. It’s like asking them to do half your job for you and it delivers a strong message: “I know nothing of your company and I don’t care.

Trish Bertuzzi gets a lot of these emails -- and she gets pissed off every time. I’m talking about this kind of email:

The best way to avoid this is by doing your homework during the prospecting process and finding the right decision maker to reach out to.

How to find the right decision maker?

If you’re selling to a large company with many sections, directors, and managers, look for the sections related to your product. For example, if you’re selling a sales-related product -- like a sales management platform -- you should contact a sales manager or director.

It’s reasonable to assume a director has a more purchasing power, so reaching out to them might be more fruitful.

If you’re targeting a small company or startup, the right decision maker is likely the CEO. So, unless you find a different director or manager responsible for a section -- like a content marketing manager or social media manager) -- confidently reach out to the CEO.

As a rule of thumb, you can guess the decision maker based on the company’s size:

  1. 0-10 employees: The decision maker is usually the CEO, unless the company has co-founders in the vertical you’re selling into (e.g., CTO for Product, CMO for Marketing) or has experienced VPs.
  2. 10-50 employees: VPs generally have buying power here.
  3. 50-500 employees: At this size, look for specialized roles, such as Sales Manager, Business Development Manager, etc..
  4. 500+ employees: Find regional, specialized roles, such as East Coast Rep, North America Rep, New York City Rep, etc..

Check out the company’s website or use LinkedIn or Crunchbase to find the role in a company.

Simply type the company’s name in LinkedIn’s search bar and click “See all employees on LinkedIn.” You’ll then see a list of people who work in that company.

LinkedIn’s search filters give you even greater possibilities. You can search by adding titles, schools, connections, locations, past companies, or industry to find the exact person on LinkedIn.

To find the email address of a contact, first check the company’s website. Chances are there’s an “About us” or “Our Team” page including the email addresses of people in that company. You can also check out their LinkedIn profile and click on “Contact and Personal Info” to see if they’ve included an email there.

Speaking of LinkedIn -- don’t forget you can export connection email addresses. Simply head over to the “My Network” tab and click “See all” on the right side of the screen.

Then, click on “Manage synced and imported contacts” and “export contacts” to have a spreadsheet of your connections’ contact information.

If you’ve had no luck with their website or LinkedIn profile, search their names to find out if they have a personal website. You should be able to find an email address there.

If this didn’t work out, you can do some guessing.

Typically, the email address of a company’s employees is formatted in one of these ways:

  • first@company.com
  • first.last@company.com
  • firstlast@company.com
  • firstinitiallastname@company.com
  • firstlastinitial@company.com

You can test each one of these formats in MailTester to find the right one.

Alternatively, use a Chrome extension called Sales Navigator by LinkedIn to find out if an email address is associated with a LinkedIn account.

How do you know if a company has a buying intent?

  1. If they engage with your content: Assuming you’re producing and sharing the right kind of content on your blog and social media, you can be quite certain a company’s representative engaging with your content is interested in your product.
  2. If they engage with your competitor’s content: Have an eye on your competitors’ blog and social feed. If relevant roles in a company engage with them, it could be a signal of their buying intent. You can also check competitors’ social followers to find a valuable point of contact. Monitoring your competitors’ content is a great way to out-market them.
  3. If they mention some industry-related keywords: Mentioning some keywords on social media might signal buying intent. To monitor keywords and mentions, use social media monitoring tools such as Mention or Brand24.

Some free social monitoring tools include Hootsuite (Allows to monitor mentions of a keyword on Twitter), TweetDeck (A Twitter monitoring tool), SocialMention (Searches blogs, microblogs, images, and videos to find your keyword), and Boardreader (Enables you to find mentions of keywords on popular forums and messaging boards).

Mistake 2: Tricking them into opening

I’m subscribed to around 100 email newsletters, and there are a few that have earned my distrust over time. They generally use clickbait subject lines to get opens. Here are a few examples from my inbox:

  1. Want my website?” (This person was a selling his website themes)
  2. I told you not to do this” (I had no previous communication with them)
  3. Your subscription is expiring” (What subscription?)

The latest revolutionary technique of these people is using “Re:” in their subject lines without ever starting a conversation with me.

  1. Re: your invite
  2. [last chance] Re: your offer
  3. Re: Join . . . in London on October 19th - save your spot now!

I get so frustrated when I see these emails in my inbox. Send me a few clickbait emails and I’ll doubt whatever claims you make -- anytime, anywhere.

If you’re wondering what makes a clickbait title, here are some cases:

    1. Deceptive about who the email is from:Did I leave my jacket at your place?” seems to be from a friend, but it’s not.
    2. Deceptive about previous email exchanges: the blatant “Re:” type
    3. Deceptive about urgency of a message:Urgent -- Update your information.” You click on it just to find it’s a promotional email.
    4. Deceptive about action taken by the subscriber: Your Reservation Confirmation,” “About your order,” “Thanks for your order!

So, how do you write email subject lines that are attention grabbing and honest?

There are two things you need to do:

  1. Be relevant: Citing the article they’ve written, a person you both know, any new projects their company is working on, or a problem they’re facing (and how to solve it) will make your subject line more relevant. Subject lines like, “We both know [a person]” or “A word on your [name of the project],” “Could your sales team produce more leads? Here’s how,” or “How I lost your Sperry's ... and why you should meet with me” still rock.
  2. Use your industry’s hottest news: If a personality, product, number, or practice is trending in your industry, use it in your subject line. It will pique the receiver's interest and get a click. Some examples are “Facebook dropped the ball -- we picked it up,” “The new Amazon feature rocks but there’s a catch,” and “AI helping you get more leads?” If you’re not sure about how to position your product while entertaining the receiver, consider talking to an expert consultant.

Mistake 3: Not establishing a personal connection

Ever received one of those emails brimming with “I’s” and “We’s?” The kind of emails that refer repeatedly to the sender, what they like, what they find interesting, and what they plan to do. A typical response to those deluded self-flattering sales people is “Do I know you? Why should I care?” If you’re a busy C-level manager, you won’t even think about it -- you hit delete immediately.

I’m not telling you not to introduce yourself or mention what you do. I am saying the main character in your sales pitch should be the receiver, not the sender. You should write about their stuff, not yours. Using “I’s” and “We’s” is no problem if the main character of the sales pitch is still the receiver (Check out the template below).

Before you send an email, research the following:

    1. The person you’re sending the email to: Visit their personal website, sign up for their newsletter (and tell them about it in your email), read their content, see if they were mentioned in the news, research their position and tenure at the company, and find out who they’ve worked with and the challenges they face.
    2. The company’s recent news: See if the company has had a recent achievement, reputable client, an article featured in a major publication, or a new feature released. Make sure none of the challenges or wins they experience go unnoticed.

Use this information in your sales pitch to make it more personal. Here’s a personalized cold email template for a company offering prospecting solutions:

There are a few things I’m considering in this email:

  1. My subject line is interesting for any decision maker in a SaaS business, and it’s a question and promise to solve a problem.
  2. I’m comparing the receiver with a famous thought leader in my niche, so they’ll be flattered.
  3. I’m mentioning their company’s biggest achievement: Working with impressive clients.
  4. I’m positioning my company’s platform as a product that will help them achieve their goal: Having more qualified leads.
  5. I’m establishing my company’s credibility by mentioning our biggest achievements (The number of leads we’ve delivered and our greatest clients.).
  6. I know they already have a sales management platform, so they must be worried about integration issues. I assure them that’s no problem.
  7. I end the email with one easy question. Once they answer, we’ll discuss whether the demo would be online, on site, or on the phone.

Mistake 4: Offering too many benefits

Many cold emails go unanswered because they leave the receiver in decision paralysis. They provide too many options to choose from and ask for too many things.

Determine one core benefit to deliver in your sales pitch. Build your pitch on top of that core benefit and prove yourself credible by citing past achievements.

So, how do you arrive at an effective core benefit? Here are some points to consider:

  1. An effective core benefit transforms the receiver's current self to a desired self. As Consulting explains, people are extremely driven by the desire to be transformed from their current self to an ideal self.
  2. Research your receiver’s pain points and potential needs and position your product as a solution to their problem.
  3. Prove yourself credible by citing past experience and big clients.

End your sales pitch with a clear question. Here are some effective options to try:

  • Would this be a problem for you?Assuming you’ve explained a possible problem they’re facing -- such as having too many cold leads -- in your sales pitch, ask this question to ensure they’re on the same page.
  • Interested in a free demo of how our platform can [cite the benefit]?You’ve identified their problem and offered your platform as a solution. This is the most risk-free benefit-loaded question you can ask. Once you receive a “Yes,” discuss if the demo will be delivered in person or online.
  • I think the best way to discuss what we can do for you is over the phone. Would you be interested in that?Most busy business people aren’t a fan of this question, but if you’ve personalized your email, identified their problem correctly, and positioned yourself the right way, they should be interested in a phone chat with you.

Here’s another cold email template with a core benefit offered:

Mistake 5: Not following up

Cold emailing isn’t a numbers game. If the contacts you’re reaching out to show strong intent to buy because they’ve engaged with your competitors or mentioned industry keywords, you’ll enjoy a higher rate of success.

If you don’t hear back from a prospect, take a deep breath and follow up on your previous email with another well-crafted one. In many cases, it takes eight emails to book a meeting with a contact.

There are some reasons why you should send follow-up emails:

  1. As a salesperson, persistence is the primary skill you need.
  2. It showcases your self-confidence in sales.
  3. It keeps you a top-of-mind solution to a very real problem.

When to start sending your follow-up emails?

Follow up one week after sending your original sales pitch. Send your next follow up ten days later and the next one two weeks after that. Space out the following emails, sending one three weeks later, then one every month, every other month, and, finally, every three months.

What to include in your follow-up email?

Include a short recap of your sales pitch and an easy question at the end of each follow-up email. Here’s a template:

Respect your receiver's time by being concise, show their response is important to you, and remember they don’t owe you a response.

Here’s an annoying follow-up email I got recently:

“Ummm, okay, this is the last time you’ll hear from me -- pinky swear.

Did you happen to check out our article on developing our own mobile marketing strategy?

If you don’t reply, I’ll assume you were kidnapped by wolves and are now being raised as one of their own in the wilderness.”

That’s it.

It’s offensive (especially if sent to a C-level manager) and blames me for not replying.

I had no idea why I should have checked out their article or even what the article was. After reading the original email, I realized they wanted a link to their mobile marketing strategy article simply because I’d linked to one by another company. To me it seemed like a lame incentive. Why should I ever do that?

Boosting your response rate and landing more clients through your sales pitches is not easy work. It needs testing and measuring.

A very low response rate from your cold emails might happen if you contact the wrong person, use clickbait subject lines, don’t send a relevant or personalized sales email, offer multiple benefits in your email, or don’t follow up. Avoid these five lethal prospecting email mistakes and you’ll find great success.

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