Why your top priority should be to teach your sales team to write

Kayla Lee
The Startup
Published in
9 min readSep 18, 2018


Photo by rawpixel on Unsplash

We all write every day — emails, texts, Slacks, Snaps, landing pages, ads, proposals, LinkedIn messages, and so on.

Businesses run on writing. Great businesses run on great writing.

It doesn’t matter if the person is a marketer, salesperson, designer, programmer, or whatever, their writing skills will pay off. That’s because being a good writer is about more than writing clear writing. Clear writing is a sign of clear thinking. Great writers know how to communicate. They make things easy to understand.

Jason Fried

But, most Americans aren’t good writers.

  • 75% of middle schoolers have below-average writing skills.
  • 40% of students who took the ACT in 2016 didn’t perform well enough to get through a basic English composition class in college.
  • 2300 college students’ writing was tested — conclusion? Most of them couldn’t write a complete sentence.
  • Hundreds of employers complain about horrible writing — even when candidates come from elite schools.
  • The National Council on Teacher Quality looked at 2400 writing curriculums and determined that there was no systematic way of teaching writing.

Most people suck at writing because most people aren’t taught to write.

What’s more, writing a complete sentence is worlds away from writing a good sentence.

Most of the modern sales cycle is written content.

Your first contact, the proposal, the LinkedIn messages…

It’s all in writing.

Yet, we offer no training to sales staff on how to write well. Nor do we teach them to write words that sell things.

Let me show you what learning to write well (and write to sell) has done for me.

  • Good writing tripled my own business profits (as a consultant and coach). I’ve got one email that lands me 2–3 new clients every time I send it. No follow up needed. 1 email, then close—not much cycle to it.
  • Good writing helps me get leads in ways that other salespeople can’t — writing eBooks targeting my clients, blog posts, or helpful messages in Slack and LinkedIn groups.
  • Good writing gets one of my clients 5–6 meetings per week and 2–3 new deals per week.
  • Good writing has doubled the revenue of my clients’ businesses (see below).
text convo with my client the week business doubled

In a matter of a few months, good writing tripled my profits.

Imagine the difference in sales if your entire team improved 2–3X.

Poor writing kills deals

It’s all about reputation and expertise. Particularly if you’re in B2B sales. In fact, 80% of B2B buyers will only buy from a rep they feel is an expert. Poor writing makes us non-experts.

Too much text? You overwhelm the reader, and they lose interest.

Too little text? Your reader is confused.

Poor readability? Your prospect won’t know what you’re selling. They won’t know the benefits of your product or service.

Shitty grammar? Bad grammar can kill the deal half of the time. You seem less qualified. The company seems less qualified. Shitty grammar also means the message won’t be clear. Don’t make the mistake grammar as a subject meant for 8th grade. Basic grammar is essential for clarity. Think one comma doesn’t matter much?

Let’s eat Jerry. (This means you want to eat your friend, Jerry).

Let’s eat, Jerry. (This means you want to eat something with your friend, Jerry).

That tiny comma changed the whole sentence.

Shitty syntax? The benefits of your product or service get buried in a blob of confusing text.

Good writing makes for a more efficient sales cycle and more closed deals.

To improve writing, improve readability

Readability is how easy it is to read a piece of writing. Readable = clear.

The more readable, the more convincing. The more readable, the fewer back-and-forths you need to get a deal closed.

Great news — it’s not difficult to improve readability.

Professional writers and editors, such as those at The Post, know readability can be learned. They have learned how to be vivid and interesting, what to do when a sentence is screwed up by a bad verb, and why one controls sentence length.

— Valerie Strauss, The Washington Post

But won’t all this take tons of time to learn?


Professor John Maguire, at Berklee College of Music (my alma mater), conducted an experiment after realizing most of his students couldn’t write a clear sentence.

He devised a new method to teach writing composition. I’ll let him tell the rest:

Within a couple of weeks, much of the class was writing decent sentences and half-page passages made of decent sentences. They were using good verbs…

I’ve studied his method, and I think you can learn it quickly with new technologies. You don’t need to babysit your team, check their writing, or spend hours contemplating the clarity of your own words. And, you don’t have to have perfect grammar. In fact, conversational clarity (as I like to call it) is what to focus on.

Improve your writing within a couple of weeks

Step 1. Get Grammarly

Download Grammarly and the Chrome extension. It is absolutely worth the $30/mo. You’ll see 1000X ROI.

Step 2. Short-n-sweet is best

  • Keep things short-n-sweet. A sentence should be no longer than a couple of lines on a computer screen. Paragraphs should be no more than 4 lines (notice the paragraphs in this post).
  • Use small words, not big ones. Given a choice between a complex word and a simple one, let simple win. Scared > Pusillanimous.
  • Eliminate ALL unnecessary words. Mark Twain and Ernest Hemingway would spend hours weeding every unnecessary word from their work. Like this:

Don’t make the mistake of thinking the more you ramble and the bigger the words, the smarter you sound. The opposite is true. It takes a pretty smart person to explain complex products with simple words.

Step 3. Write the (real) benefits

As salespeople, we need to get to the point. Problem is, it’s sometimes hard to know what the point is. The point of any sales message is to articulate the results your product or service provides.

A good sales message is short-n-sweet — and mentions the RESULTS benefits that your company can produce for your prospect.

Results benefits: the results of working with your product/service. This is the only thing a prospect cares about. It’s tangible and is usually a metric related to your customer’s profit. (If you don’t know which metrics are most important to your customers, you need to ask them).

Results benefit example: On average our company/product increases profits by 57% in 3 months. Or, our email software will improve deliverability by X%, for an average increase in profits of Y%.

Results are most effective when communicated in dollars saved or dollars made.

To find your results benefits, start with metrics you do know. If you build websites and they improve traffic by x, then find your client’s average deal size and plug the numbers in. You drive x traffic, which results in y clicks, and z potential dollars in e-commerce sales.

Action benefits: What your product or service is. No one gives a shit about the actions you take/your product takes.

Action benefit example: We build responsive websites OR our SaaS app scores your competitors’ blog posts so you can spy on their content efforts. Or, we’re disrupting stuff.

Actions never sold a thing. Results sell everything.

What results is the picture below selling?

Nike ad

The result of buying this workout gear is a fit body that you’ll be proud of.

Or what about the #shareacoke campaign?

Coca-Cola ad

The result of sharing a coke is a closer relationship with someone you love.

Sometimes, big brands write the results benefits right into their ads.

GE ad

Big brands and ad agencies are brilliant at selling results. It’s good practice to try and pick out the results they’re selling. It’ll teach you to write results.

Step. 4 Write active verbs

Active verbs produce clarity. This is arguably the most important part of clear writing. Here’s the gist:

Active verbs: subject before verb

Example: The girl threw the ball.

Girl (subject) threw (verb) ball (object)

Passive verbs: subject after verb

Example: The ball was thrown by the girl.

Ball (object) thrown (verb) girl (subject)

As you can see, active voice is clear. It’s short and to the point. There’s nothing worse than a piece of writing full of passive voice.

The example above is simple, but imagine a more complex sentence in passive voice. It’s exhausting to read because your mind is forced to reorder the words. Your brain is like — WAIT, who. did. what. to. what. and when?

This simple rule can make or break the clarity of our words.

We’re lucky. Today, technology makes it easy for us to write in active voice.

The Grammarly app I mentioned will point out passive voice in anything written in an email, a web app, Google Doc, etc.

Don’t be discouraged if there’s lots of passive voice in your writing at first. You’ll improve quickly by noticing and correcting it.

Make sure you correct it every time. Within a month or so, you’ll write almost entirely in active voice.

Let’s take a look at an example

I get a flurry of cold emails every morning. And before we go any further — yes, they work (if done correctly). Like I mentioned above, a client of mine uses the same cold email every week and lands 5–6 meetings and 2–3 new deals per week with one email.

Problem is, most people have no idea how to write an effective email.

Look at this example

A cold email I received

I opened it and was immediately exhausted by the amount of text. My brain goes, delete it— we don’t have energy for this.

I don’t know this person, the ONLY thing I care about is how they can help my company. They keep saying, “disrupt this” and “disrupt that.” But what do I care if they disrupt anything? Wtf is a CNC machine? What do I care if they don’t own their means of production?

Here’s how we can apply the rules of clear writing to that email

  • short-n-sweet
  • talk results, not actions
  • be as clear as possible

Hi {{First Name}},

I’m Bob with DigitalFurniture. I make furniture especially for {{insert job type/company type}}. The huge benefit? I email your furniture to you. Zero wait, zero hassle.

I email a file, and a local maker near you creates your team’s {{insert furniture type}}. Best of all, you get custom pieces for a fraction of the cost — and super fast delivery times. Google and Nike love our stuff.

Do you have 2 minutes this week to talk about what type of furniture you’re looking for?

When an email is short and to the point, we’re not only increasing the rate of responses, we also weed out unqualified leads. How? Because more people read the thing.

*I’d link that line “Google and Nike love our stuff,” to a case study.


If your team isn’t writing well, you’re losing opportunities.

Good writing is clear. If you don’t feel confident in your ability to write, no worries. You can use technology to improve your skill in a matter of weeks.

  • Write small words
  • Write active verbs
  • Keep sentences to two lines of text max
  • Keep paragraphs to 4 lines of text max

Thanks for reading, if you found this helpful, please clap so that it can help others :)

If you’re interested in learning more about improving your team’s writing ability, please connect with me.

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Kayla Lee
The Startup

Writer who wants to be an engineer. Formerly, an engineer who wanted to be a writer. 🤷🏻 Skillshare class here: https://skl.sh/2H57hgN