24
E-Mail and Direct Messaging

Your e-mail inbox is a bit like a Las Vegas roulette machine. You know, you just check it and check it, and every once in a while there’s some juicy little tidbit of reward, like the three quarters that pop down on a one-armed bandit. And that keeps you coming back for more.

—Douglas Rushkoff, writer

E-mail and social media direct messaging are powerful parts of a balanced prospecting approach. Most of your prospects will have an e-mail account and almost all of them will have a social media in-box that allows you to send a direct message.

Facebook Messenger, Instagram, Twitter, LinkedIn, WhatsApp, and Snapchat are often used as proxies, supplements, or complete replacements for traditional e-mail. The benefit of the social media channel and direct messaging (DM) apps is that you may send mail to prospects even if you don’t know their e-mail address (though in most cases you need to be connected with them first).

The downside of direct messages and e-mail, in all forms, is that if you irritate your prospect by sending them spam-laden crap, they’ll block you, spam you, or unfriend you in a heartbeat. E-mail done wrong wastes your time, makes you look unprofessional, and exasperates prospects.

When leveraged intelligently, though, e-mail and direct messages engage and open conversations with prospects. E-mail done right is a powerful prospecting methodology that will reward you with a consistent stream of qualified prospects.

In this chapter you’ll learn a simple four-step framework that will instantly make your prospecting e-mails and DMs on social media more impactful and improve conversion.

The Four Cardinal Rules of E-Mail and Direct Message Prospecting

Message matters. Effective e-mail and direct message prospecting requires thoughtfulness and effort and begins with four cardinal rules (see Figure 24.1).

The figure describes the “four cardinal rules of e-mail and direct message prospecting.” It is a cyclic process that starts with compliant followed by delivered, opened, converts and the process continues.

Figure 24.1 Four Cardinal Rules of E-Mail and Direct Message Prospecting

Rule #1: Your E-Mail Must Get Delivered

If your message doesn’t get delivered you have no chance for conversion and you’ve wasted your time. Most individuals today have filters set up that either block or move “spam” e-mails to a junk folder. They may also block you from DMing them on social media.

There is no perfect science that lets you stay completely clear of spam filters. The good news is that your government e-mail address is likely to be whitelisted by most e-mail service providers, so e-mail you send will get through.

You can do additional things to increase the probability that your e-mail gets delivered. This is not a comprehensive list—rather, it’s a list of the most obvious and important tactics.

  • Don’t send bulk e-mail. Prospecting e-mail is one to one. It is one e-mail from your address sent to one individual, one e-mail at a time. This alone should help you clear 90 percent of spam hurdles. Sending bulk e-mail (the same message to multiple people) from your personal e-mail address is the easiest and fastest way to get blacklisted, get blocked, and look like a total imbecile. The same goes for creating groups on Messenger and blasting those groups.
  • Avoid attaching images. Because hackers and spammers embed malware in images, many e-mail programs mark e-mails with images as spam or block images until permission is given to download. Your best bet on prospecting e-mails is to avoid sending images. This is not the case, however, with social in-boxes.
  • Avoid hyperlinks. The primary tool of hackers is the hyperlink. You click on it, and the hacker inserts malware on your computer and steals your information. Because of this, people are super suspicious of hyperlinks embedded in e-mails and DMs. Your best bet is to avoid hyperlinks altogether in prospecting e-mails because they also trigger spam filters. If you do include a link:
    • Avoid embedding the URL in text.
    • Include the entire URL for complete transparency.
    • Avoid shortened URLs that obscure the website address.
    • Limit the total number of URLs to one—including any links in your e-mail signature.
  • Avoid attachments. Hackers have become adept at using attachments to infect computers with malware, hack websites, and infiltrate networks. Because of this danger, spam filters may block your e-mail if it contains attachments. Your best bet is to avoid sending attachments in prospecting e-mails.
  • Skip spammy words and phrases. What you say and how you say it can trigger spam filters. For example, using ALL CAPS in a subject line, adding exclamation points, or using words like free or cash can light up spam filters like a Christmas tree. Be careful and thoughtful about the symbols and words you use and how you phrase those words—especially in your e-mail subject line. The best thing to do is step into the spammer’s shoes—look at the annoying spam you get and then do the opposite.
  • Don’t send too many e-mails or DMs to the same person. This may seem counterintuitive, but with e-mail and direct messages, too much persistence can hurt you. If you become annoying, the recipient of your e-mail can mark it as spam or block you altogether.
  • Scrub bounces. Many e-mail filters will block you if you send multiple e-mails to an e-mail address that doesn’t exist. When you get a bounce, view it as an opportunity to gather better information. Update the contact in your Recruiting Information Support System and remove the e-mail address so you won’t mistakenly send to that address again. Then get to work by phone or in person to get an accurate e-mail address.

Rule #2: Your E-Mail Must Get Opened

Here’s a fact of life: People get a lot of e-mail, and there is simply no way they can possibly get to it all. Your prospects cope with being overwhelmed by an in-box that is set to “infinite refill” the same way you do: scan and triage. They, like you, must make split-second decisions to open, delete, or save for later. To get opened, your prospecting e-mail or direct message must stand out from all of the noise and be compelling enough to entice a click.

  • Familiarity gets your e-mail opened. One way to stand out is familiarity. Imagine that you are scanning your in-box. An e-mail or DM from a person you recognize catches your eye. What is the your most probable next action?

  • The law of familiarity is always in play with e-mail and direct message prospecting. The more familiar your prospect is with you, the more likely they are to open your e-mail. This is why leveraging the phone and both face-to-face and social channels before sending an e-mail or DM can increase the chances of getting your message opened.
  • The layering of channels to build familiarity is powerful. For example, after meeting your prospect at an event, you might send a text, leave a voice mail, “like” something your prospect posts on Facebook, and follow that up with a DM and/or e-mail. This increases familiarity and the probability that your prospect will respond.
  • Layering prospecting channels should be focused, targeted, intentional, and strategic. You need to plan your touches across the various prospecting channels to improve opening rates for your e-mail and direct messages without becoming annoying.

  • Your subject line must scream “open me!” Depending on the level of familiarity your prospect has with you, the subject line can be the most important key to getting your e-mail opened. Sadly, though, most prospecting e-mail subject lines neither stand out nor are compelling. Most, in fact, scream “delete me!”

These are the three most common subject line mistakes:

  1. They’re too long. Data from many sources prove that shorter subject lines outperform longer subject lines by wide margins. Frankly, it’s intuitive. A long subject line requires your prospect’s brain to work harder. In the context of split-second decisions about the value of an e-mail, that extra effort gets you deleted.

  • Most of the e-mail messages you send your prospects will be opened on a mobile device. If you consider your own behavior on your mobile phone, you are quicker to delete a message there. Put more than 50 characters in your subject line, and the open rate goes down exponentially.
  • Solution: Keep e-mail prospecting subject lines super short—three to six words or 40 to 50 characters including spaces. Remember—less is more.

  1. They include questions. E-mail prospecting subject lines in the form of questions are delete bait. Virtually every major study conducted on the efficacy of different types of e-mail subject lines has concluded that subject lines in the form of a question quickly doom your e-mail to the delete-button death-roll. Though there may be a time and place for using a question in your e-mail subject line, in most cases you should step away from the question mark.

  • Solution: Use action words and directive statements instead of questions. List-based subject lines that include a testimonial like “Three Reasons Why a Military Career Will Make You Stronger” are especially powerful, as are referral subject lines like “Jeb Blount Said We Should Talk” and statement-based subject lines like “Adventure Awaits You.”

  1. They’re impersonal or boring. Generic, impersonal subject lines—usually ones that are about you and your branch—are boring. When you are attempting to engage prospects—especially overstimulated teenagers—a failure to grab their attention will send you straight to the trash.

  • Think about it. Every recruiter in the military, colleges, and the private sector is trying to connect with the highest-value prospects in your market. These top prospects are inundated with requests for interviews and meetings. You will never break through this noise and get their attention with boring, cheesy, or impersonal subject lines. Instead of standing out, you’ll just be another person junking up your prospect’s in-box and wasting their time.
  • Solution: Connect your subject line to an issue your prospect is facing—especially if it is emotional or stressful—or compliment them on a recent accomplishment or something that you know makes them feel proud. For example, the easiest, fastest way to get me to open your e-mail is a subject line that reads: “Loved Your Book!” You can also use relevant humor or tongue-in-cheek phrases to catch your prospect’s attention when appropriate.
  • We are all self-centered and almost always focused on our own problems, issues, accomplishments, and ego. The fact is, 95 percent of the time we are thinking about ourselves, and the 5 percent of time that we are not thinking about ourselves, something—maybe a mouthy recruiter—has gotten in the way of us thinking about ourselves.
  • So play the odds, and make your subject line about your prospect. It’s really easy to do if you take a little extra time to research the recipient of your prospecting e-mail.

The brutal reality, though, is there is no secret formula for creating the perfect e-mail subject line every time. What works with one group of prospects may not work with another. This is why experimentation and testing are the real secrets to success with subject lines.

Testing helps you zero in on which subject lines get the most opens. With this data in hand, you’ll often find patterns that lead to subject lines that work phenomenally well with certain prospect groups.

Yet most recruiters don’t test. Instead, they create subject lines on the fly and then send their e-mails into a black hole, hoping that they’ll get a response. It’s an incredibly frustrating way to prospect because it’s like throwing darts at a target while blindfolded and hoping you hit a bull’s-eye, without any feedback to let you know if your aim is true.

With this information, you’ll be able to narrow down and home in on the words and phrases that get the best response, and your e-mails will stand out and get opened.

Rule #3: Your E-Mail Must Convert

Unless you are sending pure spam—generic e-mail and DM templates that are copied and pasted, then sent randomly to a large swath of prospects regardless of relevance and with no research—developing and crafting effective messaging requires a significant investment in time.

To engage highest-qualified prospects, you will need to personalize each e-mail message. Thought and effort will be required to craft a relevant e-mail that connects with the most desirable prospects and moves them to take action.

This doesn’t mean that every e-mail you send must be built from scratch. Certainly, within specific targeted demographics there will be enough common ground and patterns that you’ll be able to develop templates that can be easily customized. These customizable templates allow you to deliver more prospecting e-mail and DM touches in a shorter period of time.

Even with a customizable template, though, to be effective, you must do research so the message looks and feels unique to the recipient. It will fall on deaf ears if the recipient doesn’t feel that it was crafted specifically for them.

This costly investment of your precious and limited time is why it is imperative that your prospecting e-mails and DMs convert. In other words, generating a response that leads to your desired outcome:

  • An interview
  • Connecting with you on social media
  • Qualifying information
  • Accepting an invite to meet you at an event
  • Viewing a video or clicking on a link
  • A recruiting conversation

If your message doesn’t compel the recipient to take action, your time and effort were wasted. This is why investing the time to get your message right is critical.

Rule #4: Your E-Mail Must Be Compliant

There are rules and laws governing e-mail communication. Ensure that you know and comply with regulations.

Effective Prospecting E-Mail and Direct Messages Begins with a Plan

A plan helps you define who will be getting your e-mail, the method or technique you will use to get their attention, the message you will craft to connect with them and compel them to take action, and finally, the action you want the recipient to take. With e-mail and DM prospecting, this is your AMMO (see Figure 24.2):

The figure diagrammatically explains  an “e-mail AMMO,” that is audience, method, message, and outcome. It helps define who will be getting your e-mail, the method or technique you will use to get their attention.

Figure 24.2 E-mail AMMO

You don’t have to look far to see that planning is rare when it comes to prospecting messages. The vast majority of prospecting e-mail and DMs are awful.

Because I am a business owner and decision maker, I get blasted by prospecting e-mails and direct messages from every direction—on my work e-mail, LinkedIn, Twitter, and Facebook. I receive dozens each week that are laughable and embarrassments to the people who sent them.

I’m baffled at how often people who took the time to send a message to me did no research. Bad e-mail and DM messages destroy your personal brand equity, credibility, and image. The worst messages are:

  • Long, important-sounding pitches using incomprehensible jargon—a lot of words with no meaning
  • Feature dumps
  • Cheerleaders who write over and over about how great they are
  • The ones that get my name wrong—seriously, it is Jeb: three letters
  • The long ones that cause eyes to glaze over. WTF, we live in the age of Twitter, text messaging, infographics, OMGs, and LOLs. Prospects have the attention span of mosquitos.

I delete 99.9 percent of them.

Every once in a while, though, I’ll get a brilliant e-mail or DM that makes me stop in my tracks. This golden message connects with me, makes sense, is relevant, and compels me to respond. The sender took time to research and plan.

In our competitive marketplace, where talented people are in demand and have many options, in order to get their attention, message matters.

  • Consider your audience. Prospects are people—not robots—so your message should be authentic and personal. It should connect emotionally. You need to ensure that the tone, structure, and formality of your message is a match for the person you are writing. The emotional connection is vital because your e-mail or DM will be effective only if it causes your prospect to take an intended action.
  • Determine your method. Will you leverage a single, standalone e-mail or DM or a multi-message campaign? The method you choose should be driven by your intended audience and defined outcome:

  • Standalone?
  • Part of a campaign?
  • Nurturing or action oriented?
  • Cross-platform?

  • This is where planning and strategy are crucial—especially with Alpha prospects. You want to avoid being random with your most important opportunities.
  • Tailor the message to your audience. The message you craft must be strong enough to compel your prospect to take action. Your prospect wants to know that you get them and their problems, so your message must be relevant to their situation. The most effective way to tailor your message to the person you are writing is to step into their shoes:

  • What will get their attention?
  • Short and sweet?
  • More detailed?
  • Hard-hitting?
  • Soft?
  • Direct?
  • What’s important to them?
  • What will cause them to give you what you are asking for?

  • The key here is taking time to do basic research to get to know your prospect and using that information as the foundation on which you construct your message.
  • Define your desired outcome. If you don’t know what you want, you won’t get what you want. If you fail to clearly define what you are asking your prospect to do or provide, they will be confused.

The Four-Step E-mail Prospecting Framework

The AMMO framework assists you in planning and developing your strategy. Once you have your plan in place, you’ll use the Four-Step E-mail Prospecting Framework to craft your e-mail (see Figure 24.3):

  1. Hook: Get their attention with a compelling subject line and opening sentence/statement.
  2. Relate: Demonstrate that you get them and their problem. Show empathy and authenticity.
  3. Bridge: Connect the dots between their problem and how you can help them. Explain the WIIFM.
  4. Ask: Be clear and straightforward about the action you want them to take, and make it easy for them to do so.
The figure shows the “four-step e-mail prospecting framework.” It starts from hook followed by relate, bridge, and ask.

Figure 24.3 Four Step E-mail Prospecting Framework

Here is an example of a message to a prior service prospect that leverages the four-step framework:

Subject: This is why you miss wearing the uniform

Dave,

It’s 1400 hours and you’re patrolling in 120-degree weather with 60 pounds of gear on your shoulders. Life sucks! Or does it?

For many of us that have moved on, these are our best stories. Most start with, “No shit, so there I was. . .” There is nothing like the camaraderie that you get being next to your friends embracing the suck.

The civilian world can be stressful, lonely, and not all that it’s cracked up to be. I help veterans like you get back to a way of life that gives you a sense of pride and connection every time you put on the uniform. Whether it’s full or part-time, you can get back to playing with guns and blowing stuff up (who doesn’t like that?).

While I don’t know if the Army is still a good fit for you, why don’t we get together, so I can learn more about you and what you miss the most? From there, we can decide if it makes sense to keep talking. I’m going to be in your neck of the woods on Wednesday. Why don’t we meet for lunch?

SSG Early, United States Army

Hook

You have about three seconds to grab your prospect’s attention and hook them. In that three seconds, your subject line must compel them to open the e-mail, and the first sentence (especially with direct messages on social where there is no subject line) must entice them to keep reading.

Prospects choose to read your e-mail and DMs for their reasons, not yours. Therefore, the best way to hook them is to make your subject line relevant and the opening sentence about them. You must step into their shoes and focus on their unique situation and interests. Let’s take a look at our model e-mail:

Subject: This is why you miss wearing the uniform

First Sentence: It’s 1400 hours and you’re patrolling in 120-degree weather with 60 pounds of gear on your shoulders. Life sucks! Or does it?

We are writing to a prior service prospect. Both the subject line and the first sentence are emotional. We are connecting with why Dave feels like he’s missing something in his life since leaving the Army.

Relate

Effective messages connect with prospects on an emotional level. The reason is simple: People make decisions based on emotion. The easiest way to connect with your prospect emotionally is to demonstrate that you get them and their problems. You connect when you demonstrate that you can relate to their struggles and issues.

Our second paragraph steps into Dave’s shoes and lets him know that we get him. The message is authentic and genuine.

For many of us that have moved on, these are our best stories. Most start with, “No shit, so there I was. . .” There is nothing like the camaraderie that you get being next to your friends embracing the suck.

Bridge

Since prospects do things for their reasons, not yours, you must answer their most pressing question: “If I give you what you want—my time—what’s in it for me?” If you are unable to answer WIIFM with value that exceeds the cost of your prospect giving up their time, your message will not convert.

This is where your research pays off. When you know a specific issue that your prospect is facing, you should bridge directly to that issue and how you might be able to solve it. When you are unsure of a specific issue, bridge to issues that are common to your prospect’s situation.

The civilian world can be stressful, lonely, and not all that it’s cracked up to be. I help veterans like you get back to a way of life that gives you a sense of pride and connection every time you put on the uniform. Whether it’s full or part-time, you can get back to playing with guns and blowing stuff up (who doesn’t like that?).

We’ve tied our subject line, opening sentence, and relate statement together with a bridge that connects the dots between Dave’s (potential) disenchantment with the civilian world and solutions that reduce stress. We’ve answered Dave’s WIIFM question.

Most importantly, we are speaking Dave’s language—pride, connection, camaraderie, certainty, fulfillment, and fun. By speaking Dave’s language, we continue to relate and demonstrate that we get him and his problems.

Ask

To get what you want, you ask for what you want—assumptively, assertively, and confidently.

While I don’t know if the Army is still a good fit for you, why don’t we get together, so I can learn more about you and what you miss the most? From there, we can decide if it makes sense to keep talking. I’m going to be in your neck of the woods on Wednesday. Why don’t we meet for lunch?

Notice how we leverage a subtle takeaway—“While I don’t know if the Army is still a good fit for you . . .” This non-complementary behavior disrupts expectations. Telling Dave up front that this might not be a good fit is exactly the opposite of what he would expect of a recruiter. Unlike pitching that pushes prospects away, disrupting expectations (pattern painting) pulls prospects toward you.

Then we send a subtle but powerful message. We tell him that we want to learn more about him and listen to his story. This pulls Dave in deeper because everyone wants to be heard. We love to tell our story to people who are willing to listen.

Finally, we remove the stress and pressure. If it doesn’t make sense, “I’m not going to push things.” It’s just a short conversation to see if we should keep talking.

Then we assumptively (“How about”) ask for a meeting and offer a day and time, which takes the burden off Dave to make that decision.

Here are a couple of additional examples:

Subject: High school is over but it feels like something is missing

Alicia,

You’ve been out of high school for a few months now working hard to make your own way in the world. But it’s tough out there with low-paying jobs, college debt, and the high cost of everything. It feels like something is missing.

This is why so many talented people like you are taking a second look at career opportunities in the military. We offer exceptional pay and benefits, including housing, meals, medical, and education.

A military career is a fast track to financial peace of mind, travel and adventure, the pride that comes with serving your country, and friendships that will last a lifetime. But we are an exclusive club. Not everyone qualifies.

Why don’t we schedule a short call to help me learn more about you and your goals? From there, we can decide together if it makes sense to keep talking. How about Tuesday at 10:00 a.m.?

PO2 Early, United States Navy

Subject: The biggest threat to your future is college loan debt

Jeremy,

With graduation coming up soon, you’ve got big choices to make. I can’t even imagine what it must be like standing in your shoes.

CNN recently reported that the average college graduate leaves school with more than $30,000 in loan debt. Yet many college graduates are struggling to find high-paying jobs. Nobody wants to spend four years in college only to end up saddled with student debt and few job opportunities.

The good news is skilled trades are on the rise, and employers cannot find enough trained employees to fill the positions. Salary.com reports that the average aircraft mechanic makes $83,523 in the United States and Glassdoor reports that the average entry-level cybersecurity analyst makes approximately $94,490.

I help talented people like you get paid while training. You’ll gain valuable experience in high-paying trades like these, and that makes you extremely marketable.

Although I’m not sure if you even qualify for the opportunities offered by the military, I thought the best place to begin is a short call to help me learn more about you and your interests. From there, if it makes sense, we can set up a time to have a deeper conversation. How about Wednesday at 5:30 p.m.?

MSgt Early, United States Air Force

Practice, Practice, Practice

Writing effective e-mail and DM prospecting messages is not easy. The most difficult step is training yourself to step into your prospect’s shoes, relate to their situation, and learn to speak their language. Stop focusing on what you want and what you have to offer, and instead develop the habit of researching prospects and focusing on issues they are facing.

You will struggle at first. Everybody does. The key is practicing until effective, authentic e-mail messages roll off your fingertips. The more you practice, the faster and more proficient you will become at writing prospecting messages that convert.

Pause Before You Press “Send”

I am the typo king. I’m quite sure you may have found a few of my mistakes while reading this book. So I end this chapter with humble advice from a man who has made the terrible mistake of not pausing before pushing “send” and launching a typo-, misspelling-, and grammatical-error-laden message to a prospect. It is a lesson you want to avoid learning the hard way.

Proof your prospecting e-mail before you send it. Run it through spell and grammar check on your computer. Read it once. Read it twice. Print the really important e-mails and proof the hard copy. Step away from it for 10 minutes and read it again (you’ll be amazed at what you catch using this process).

Your e-mail is a reflection of you, your professionalism, and your personal brand. Pause before you push “send” to ensure that the impression you make is a positive one.

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