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Want More Deals? Teach Your Sales Reps to Write

Most sales teams hire extroverted talkers. But once they are onboarded, reps live and die by their writing, and many find themselves unprepared to compete in the inbox.

The average rep spends 20.4% of their time emailing compared to 15.7% talking on the phone or in person, an study found. The importance of email is also front-loaded: If an email is bad, reps never get to a phone call. If the email is really bad, prospects name and shame them on LinkedIn.

Want to convert more accounts? Want to win more deals? Want prospects to stop posting about how your team still sends pictures of hippos? Teach your reps to write.

Here are seven ways to improve your sales reps’ outreach:

1. Make Your Own Templates

Using templates to guide reps is wise. Borrowing them is not. Any template that’s broad enough to apply to all the readers of a widely-read sales blog hasn’t been tested with your audience and isn’t tailored to your buyer and industry. It’s also the same exact format every other salesperson uses. Make your own from scratch based on what actually works.

“Not every sales rep needs to be a skilled writer to succeed. But for the sake of your team’s performance and your brand, someone needs to make sure the standardized portions of your outbound sales communications are authentic, accurate, and match the challenges of your target or market persona,” said Alex Boyd, founder of the demand generation agency RevenueZen.

Once you have templates, never settle. Use a sales automation tool to A/B test messages across teams, share knowledge, and revise.

Takeaway: Appoint or hire a template writer and let them a test.

2. Stop Saying “I”

Chatbots are proof that even the simplest scripted conversations go off the rails quickly, and templates only get you so far. It’s up to your reps to make clever choices when personalizing their messages and responses. For example, not writing things that make them seem narcissistic.

Sales emails often overuse the pronoun “I” and begin by telling prospects what “I would love” to do. But prospects couldn’t possibly care less.

“Excitement about your own product doesn’t compensate for being selfish,” said Pete Caputa, CEO of Databox, about a noxious email he received. Instead, “the first line of a prospecting email should always be about the prospect, never about the salesperson.”

Teach your reps to review their emails to replace every “I” with “you” and then rewrite until it makes sense. Some I’s are unavoidable, but the exercise teaches reps to write about their prospect.

Takeaway: Have reps replace every “I” with “you” and rewrite the message until it makes sense.

3. Search Before You Send

If reps ever have difficulty coming up with something to say, their email is too cold. They don’t know enough to even begin relating to their prospect.

Steve Bookbinder, CEO of DM Training, recommends always researching prospects before writing, especially on social media. “Their feeds will give you major tips about what’s going on in their life, the way they communicate with others, and maybe even give you an understanding of their career triumphs and pressure points.” It also prepares you to mirror their tone.

If the prospect has a scathing wit and likes memes from the darkly-humored TV series Rick and Morty, some sarcasm may be okay in the exchange. If they seem buttoned-up and address colleagues by their full name, it’s probably best to use formal language. Read them, mimic them, and write to them.

Takeaway: Encourage reps to study prospects’ social media to mimic their tone and style.

4. Be Honest in Your Subject Line

If reps promise something in their subject line, their message must deliver. If they don’t, they’ve only set prospects up to feel abused, indignant, and eager to do the opposite of whatever is asked. If you can write a clever subject that relates, great. But it’s better to just be straightforward and literal than misleading and burn a bridge.

Plenty has been written elsewhere on how to write outbound subject lines, but here are a few tips that have always worked for me:

  • Say unusual things: Don’t send what everyone else is sending. Instead, interrupt the pattern and write as you would to a friend.

  • Front-load keywords: Put the most important words first.

  • Don’t capitalize the first word: Executives often do this, and it can make you seem like someone the prospect should listen to.

  • Omit needless words: Never use three words where one will do, and always use a shorter word if it doesn’t alter the meaning.

  • Use evocative verbs: Replace ‘surprise’ with ‘shock,’ ‘increase’ with ‘boost,’ and so on.

Takeaway: Don’t send subject lines that are sensational and misleading.

5. Write Less

You have just a few seconds to catch prospects with your subject line. If they open, you have another few seconds. That’s it. Don’t waste a single word—like most reps do.

Most reps take a shotgun approach and cram as much information into their email as possible. They believe that at least one of their many bullet points will stick. But this makes for a terrible user experience. Prospects will open what looks like an instruction manual, read nothing, and delete. Far better to write less and be read.

“Keep things short and sweet … by keeping your email focused on one core idea or benefit,” wrote Heather R Morgan, founder of SalesFolk, in an article about starting conversations. Shortening messages also makes them more relevant: If reps can only say one thing, they’re going to invest more effort into selecting the most critical point.

Takeaway: Have reps shorten their messages with a limit, say, 150 words. Stick to it.

6. Replace Clichés and Buzzwords with Precise Language

Clichés are phrases that are so overused they’ve lost all meaning, like telling a prospect you’ll drive their business forward. Unless you’re Uber, that’s just confusing. Buzzwords are similar: they’re so fashionable that everyone uses them everywhere—as happened with “AI”—and they’ve stopped meaning what they used to. Together, clichés and buzzwords make emails indecipherable.

For example:

I’d love to tell you about our next-generation AI data processing solution that helps business owners such as yourself push the envelope, increase engagement, and disrupt the market.

Teach your reps to do the hard thing: Learn how the prospect’s business actually works and actually explain how they’ll change it. For example, replace:

  • ‘Solution’ with software, app, or service

  • ‘Bandwidth’ with capacity or time

  • ‘Core competency’ with the advantage

  • ‘Business results’ with 14 percent more inbound leads, like X customer

  • ‘Streamline’ with cut your support agents’ workflow in half

  • ‘Move the needle’ by lifting your average revenue per user

  • ‘Business value’ with literally anything else

And so on. Here’s a list of replacements.

And then, there’s jargon: Phrases that aren’t easily understood by people outside a particular industry such as ‘intelligent chat’ or ‘PaaS.’ Prospects probably won’t understand your jargon, especially if your marketing team invented the word and it has a ™ symbol. When in doubt, skip the jargon and explain the product in plain English.

Precision and brevity don’t always go hand-in-hand. Sometimes being specific makes your email longer, but it’s better to be precise and understood than vague and ignored.

Takeaway: Keep an ongoing list of clichés, buzzwords, and jargon on your wall. Remind reps to be specific and write phrases prospects actually understand.

7. Edit Before Sending

Works of persuasive art are only produced through thousands of hours of sweat. Encourage your reps to read, copy, and borrow everything good they see in print. Have them subscribe to other companies’ newsletters, screenshot good ads, and preview each other’s emails.

Once your reps have written something, make them sit on the email for a day, and then edit. It’s only through conscious practice that they’ll improve at writing and cease to bore their readers with monotonous offers to solutionize their business, and instead, awe them with a single sentence that earns the reply, “Wow, good timing. Let’s talk.”



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