Improving Influence and Persuasion by Developing “Writing EQ”

by Scott - 17 Comments

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Have you ever noticed that a smiley face at the end of the same exact sentence can completely change how someone interprets what you say?

Compare the following:

Let’s make sure this never happens again.

Let’s make sure this never happens again : )

In my experience something as simple as a smiley face can be the difference between coming off nice vs. appearing like a jerk.

Slight nuances in the syntax, punctuation, structure and semantics of your sentences can profoundly change the meaning and tone of anything you write. Any marketer or salesperson looking to persuade and influence should be acutely aware of this.

Below you’ll find a few examples where slight a variance in communication can influence how someone might interpret a statement:

Example 1: Word Choice

We’re building a new sales tool.

We’re building a new sales solution.

Difference: tool vs. solution

Interpretation: Me and my business partner talk about this all the time. Using the word tool to describe your product makes it seem like an incremental improvement or commodity. It feels small and undifferentiated vs. comprehensive and potentially game-changing.

Example 2: Capitalization

want to grab drinks tues?

Want to grab drinks tues?

Difference: want vs. Want

Interpretation: Though I’m a stickler for good grammar, there is a time and place to throw capitalization out the window. Uncapitalized statements seem more causal. So if there are instances where you want to position something as “not a big deal” you might be better served not capitalizing an ask.

Example 3: Follow up To-Do or Ask Emails

The next steps are to sign the NDA, integrate your email, and invite your co-worker then you’ll be all set.


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Difference: Structuring to-do items in a sentence vs. series of checkboxes

Interpretation: Which structure do you think yields higher compliance? Though I don’t have empirical evidence, I believe the latter does…people love the feeling of “checking something off their list!”

I pulled this example from an onboarding email I use for Troops. The great thing about this strategy is that as people complete action items, you can update follow up emails with checked boxes. For example

Email 1:

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Follow up Email:

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You can copy these checkboxes from Evernote and paste them into an email or template.

Example 4: Email Address

Hey Mark,

Hi Mark,

Difference: Hey vs. Hi

Interpretation: You always want to calibrate your tone with your audience, but generally I mostly use ‘Hey’ in cold emails. Less formal is better in most instances.

When someone emails me Dear. the immediate thin slice is that this person does not know me and I want to delete it. Very different from a stranger who emails me with “Hey.”

Example 5: Email Ask Structure 2

I’m sure you’ve seen this before, but check out the difference visually in how this might seem in the middle of a 4-6 sentence email.

“I’m looking for an iOS Lead or UX/UI designer.”


I’m looking for two things:

Difference: highlighting something you want people to be aware of in a sentence vs. indented call out.

I’ve tended to get better results when I make indentations that clearly highlight exactly what I want someone to be aware of.

So much of our business and social interactions are processed in rushed, asynchronous environments without the luxury of body language or verbal tonality. Think about how much of your job is done over email and social life through text!?

As a result, decisions are made in fractions of a second on whether someone will or will not do what you want.

This is why understanding the nuance of structure, punctuation, and semantics is so imperative. Extreme attention to detail may seem feeble, but all of these little nuances really do make a difference!

I think the best way to develop “Writing EQ” is to write consistently, put yourself out there (ask for stuff), and always try to calibrate your actions with results. Eventually, all of this stuff will become second nature.

What examples can you think of where punctuation, structure, or semantics completely change the meaning of something?


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17 comments, add to the conversation.

  1. Brandon

    great tips! I really noticed the difference when I started writing my emails in a less formal tone. I used to be the one writing overly formal with the strictest grammar hoping to come off as more professional… ew.

    Then I heard a wise man suggest asking yourself “is this how you would want to interact with someone at a bar?” 🙂

    We all receive so many emails a day I think it’s very refreshing when people can make a monotonous task just a little more fun.


  2. Scott Foubister

    Great tips, Scott! Using bullet points and checkboxes in an email really goes the extra mile to help the other person process your email efficiently and be more likely to do what you want them to do.


    1. Post Author Scott

      I just usually say Best, if anything. I pretty much always include a P.S. with a personal touch because I feel like people skip down to that part


  3. Jo

    Great stuff Scott thanks! I’ve not been brave enough to start a cold email with “hey xx”. I use “hey” with people I already know. …It’s such a lovely friendly start. I sometimes receive emails that just start “Jo”… I hate that. .. makes me feel like I’m being told off!


  4. Trevor

    Hey Scott, this info was helpful. I usually always use proper grammar, and really notice it in text when people don’t. Even though it’s hard to break out of this, sometimes it might convey a different message to be more relaxed. It reminded me of a podcast I listened to a while back where the hosts tried to stop using exclamation points for one month. It brings up a good point, especially for text messages, how do you show you’re EXCITED, without exclamation points? (! = No). Here’s the link if anyone is curious, I’m not affiliated with NPR, it’s just a funny show.
    Episode 195: F-Bombs, Chicken, and Exclamation Points


    1. Post Author Scott

      I think it’s all about context, you’re relationship, and how you’re trying to convey yourself. I really notice grammar too and generally air on the side of using proper grammar : )


  5. Jason

    Thanks for article.

    I especially liked hey or hi issue with email.

    Have a question for you on this. I mostly use ‘Dear’ because of I’m not sure if it’s appropriate to use ‘hey’ or ‘hi’. But It looks to me that using ‘hey’ is acceptable in technology and creative sectors.

    My question is is it appropriate to use ‘hey’ or ‘hi’ when contacting: people you admire, exec level people in medium sized or bigger companies (including IT and other creative sectors), or people in other traditional, less creative sectors, such as accounting, manufacturing, mass transportation, etc..?

    Sorry it’s a bit long. But I’d really appreciate your input on this. It’s one of those little issues I constantly come across when I try to connect with people.


    1. Post Author Scott

      Dear to me is like when someone calls my house and says “hello may I speak with so and so” – it immediately fires a warning signal to me that this person doesn’t know me. Even if you don’t know someone, you want to put yourself in the bucket of friend and in order to do that you should use language that their friends use! Just my two cents


  6. Mark

    In response to your question at the end, here’s an example where punctuation use can be critical…
    – Let’s eat Grandma!
    – Let’s eat, Grandma!
    A comma can save a life…! 🙂


  7. Christian

    Thanks for these tips! The bulleted list and pre-filled checklist are so simple, yet never thought to do so. Less work for the recipient to process, always good 🙂
    Plain-text version, you can also do something like:
    [x] Sign NDA
    [ ] Integrate your email
    [ ] Invite your coworker


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