The “Rules of the Road” for Writing Emails That Will Win Over Prospects

November 29, 2019

Sara Howshar

Creating compelling, personalized emails that will resonate with prospects takes focused effort. But it can be an easier task — and a much more fruitful endeavor — when you have some clear rules of the road and a repeatable, scalable process to follow.

Becc Holland, Sales Director at, has some inspired strategies to help sales pros perfect the art of email outreach. She breaks them down in a recent episode of our webinar series, “Flip the Script,” and explains how switching from mass-blast emails to personalized outreach can help make you a lethal prospector — fast. Here’s a look at some of her top tips:

Focus on structure first: premise line, body and CTA #

Becc says the first step to developing a killer prospect email is to focus on its structure. “Think of your email as the face of a clock,” she suggests.

Your prospect is likely to look at the end of the first line of your email first. Next, they’ll look toward the end of the last line. And then, if they get that far, they’ll look at the body of the email. So, with that in mind, Becc advises using no more than four lines in a prospect email:

  • The first line, or the premise line, should be the longest because the prospect is inclined to look at it first. “The premise line states why you’ve reached out,” says Becc.
  • The second line — or, the body — is the least valuable real estate in the email, says Becc. It should be of medium length and contain the value proposition you’re offering.
  • The last line, which should be the shortest of the four, contains the call to action (CTA). “This should be a simple and clear ask,” Becc says. She offers this example: “Will you give me a few minutes at 2 p.m. on Wednesday to unpack this, and, if you don’t think I can help you, then so be it?”

To get prospects to open your emails, make sure your subject line is succinct, engaging and, most of all, honest.

“Don’t try to ‘bait-and-switch’ the prospect,” says Becc. “If the email subject line bears absolutely no relation to the purpose of the email itself, it will turn off the recipient immediately and make them even less likely to open your follow-up emails."

Personalize the email with a compelling premise #

So, how do you choose your premise — the reason you’re giving the prospect for reaching out? First, pick your premise category. In another recent episode of “Flip the Script,” Becc laid out four premise categories, which she also refers to as “-graphic principles,” that sales pros can use to personalize their emails to prospects. Following is a quick review of those categories:

  • A firmagraphic premise, which relates to news about the prospect’s company — for example, maybe the firm just hired some new sales reps or announced sales results.
  • A technographic premise, which typically focuses on a company’s tech stack and how it integrates with your product.
  • A demographic premise, which relates to a prospect’s age group, level of education or, more commonly, their industry or profession.
  • A psychographic premise, which is Becc’s brainchild, born from her mission to find something more effective than the other three, commonly used categories.

“The psychographic premise involves what someone believes, what they are interested in, or maybe, something they have an attitude towards. It hits them a little bit more at their core and so, they are more likely to respond to it,” Becc explains.

After researching and testing some theories, Becc defined five psychographic premise “buckets” that sales reps can dip into to find information that can help them make a connection with a prospect. They buckets, and examples of what they include, are ranked below by the highest to lowest trigger rates:

  1. Self-authored content (e.g., a blog post the prospect wrote)
  2. Engaged content (e.g., content the prospect liked or shared)
  3. Self-attributed traits (e.g., something the person does well)
  4. Junk drawer (e.g., a prospect’s hobby or a school they attended)
  5. The prospect’s company (e.g., relevant news about the company)

For a deep-dive on these five buckets, check out this blog post, How to Personalize at Scale.

Follow Chuck Jones’s Rules of the Road (Runner) #

Once you have your email structure and premise set, it’s time to build messaging that the prospect is likely to find attractive — but is also consistent with your overall messaging. For this process, Becc looked to animation “Super Genius” Chuck Jones for inspiration. Jones developed nine strict rules for his animation team to follow when creating cartoons featuring Looney Tunes characters Road Runner and Wile E. Coyote. Examples of these rules include: “The Coyote may not catch the Road Runner!’” and “Whenever possible, make gravity the Coyote’s greatest enemy.”

Becc created her own rules of the road for personalizing emails, which she’s broken down into the 7 Pillars of Attractive Messaging and the 7 Deadly Sins of Messaging. These “do” and “don’t” lists are described below:

The 7 Pillars of Attractive Messaging #

First up, we have Becc’s list of do’s for prospect outreach:

  1. DO focus on your prospect. Becc says every word in your email to a prospect should be about the prospect. To encourage her sales development reps (SDRs) to think this way, Becc says she asks them to be aggressive about the amount of research they do on prospects — not how many emails they send.
  2. DO focus on your prospect’s pain points. Becc thinks about this “do” in the context of a hospital stay she had a few years ago. “I was in pain, lying in my hospital bed, and thinking that if I had $5,000 right now, would I spend it on a pill to relieve the pain or save it for a trip to Cabo once I’m better? I decided on the pill,” she says. The same thinking applies to most buyers. Your message will resonate more if you can show prospects how you can relieve their everyday pains, rather than focusing on how cool your product is.
  3. DO be pride-averse. Talking about yourself can be a turn-off to prospects. Try building rapport with them instead, as it can make a great impression. To do that, you really need to know who you’re talking to, says Becc. She recalls running into a VP of Sales at Pandora who told her that he remembered the first conversation they’d had. “In that initial conversation, I had told him that I’d been following his career for three years, and gave him five good reasons why I prefer Pandora over Spotify,” she says. “He told me that changed the tide of whether he was interested in my product or not.”
  4. DO write fluidly. Make sure your email flows for the reader by connecting the premise to the body and the CTA. The easiest way to do this is to stay with the same language and value props in all three segments of the email. “The biggest mistake SDRs make is to mix up the value props or jam too many of them into one email. Pick one and nail it home,” Becc advises.
  5. DO be relevant. Know who you’re selling to because not every buyer persona at a company wants or needs the same thing. “If someone asks me what does, I don’t answer until I know more about them,” says Becc.
  6. DO be brief. Never use seven words when four will do.

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