9 Ways You're Projecting Insecurity Over Email

Insecurity is poison to a sales relationship. If your prospect picks up on any anxiety or self-doubt, they’ll lose respect for you -- and more importantly, they won’t believe your recommendations are valuable.

So what can you do to project confidence? It’s tricky, especially because in sales you often go from feeling like a champion to a failure in single week (sometimes a single day).

One of the easiest areas to tackle is email. Prospects can’t see your face or hear your voice, meaning following these suggestions will instantly make you seem confident. Here are seven things making you appear insecure and how to fix them.

1. Writing too much

Emails that go on and on scream insecurity. After all, if you believe your message is powerful and compelling, you don’t need to write a book.

Next time you’re sending an email for the first time that’s three-plus paragraphs, stop and pick out the most compelling point. Delete the other sections. You can send these in follow-up emails. (As an added benefit, this makes your messages more varied and gives the buyer a reason to keep opening them.)

Just make sure you don’t leave out the call-to-action -- that's one of the most important parts of your message.

2. Apologizing

Do you begin emails with lines like:

• “Apologies for contacting you out of the blue.”
• “Hope I’m not bothering you.”
• “I’m sorry to trouble you.”
• “I know we haven’t met, but …”
• “Hopefully you don’t mind me reaching out.”
• “I know emails like these can be annoying, so I’ll get right to the point.”

These lines are usually used with good intentions: Reps want to show consideration for their prospects. However, starting with an apology implies you don’t think you’re worthy of the buyer’s time.

If you believe in your product’s value, and you’ve done some basic qualification to ensure your prospect is a potential fit, then you’re not wasting their time. You’re helping them.

3. Using too many emojis

Emojis can add personality to your email and make it a little more memorable. But it’s easy to go overboard. If every line has its own symbol, you’ll look like you’re trying way too hard.

How many emojis is too many? It depends on your market. In many conservative industries, just one smiley face would be completely inappropriate. Yet someone in an informal, modern industry tends to be far more receptive.

Factor in your company brand as well. If it’s playful, you can be playful too. If it’s relatively buttoned-up, reign in the emojis and smiley faces.

My final recommendation: When in doubt, leave it out. You can always wait and see what your prospect does. If they use a smiley face or emoji, you’re free to use one too.

4. Using exclamation marks

I admit, I used to have a real exclamation mark problem. Any time I wrote an email without one, I worried I came across as cold.

But then I realized most of the emails I got from other people didn’t include exclamation marks, and I wasn’t reading them as rude. Those messages simply seemed professional

Now, I never use exclamation marks. They’re never necessary -- especially not in a sales context. You sound 10 times more composed and sure of yourself when you’re not ending any sentences like this!

5. Going too far with flattery

Reps often throw in phrases that highlight their prospect’s intense work schedule. That includes statements like:

• “I’m sure you’re busy …”
• “As [title], you must have a lot on your plate …”
• “I know your schedule is probably jam-packed …”
• “Is there any way I could borrow just a few minutes of your time?”
• “You can’t have much extra time, so I promise I’ll be quick.”

Unfortunately, prospects interpret these lines as: “You’re busy, and I’m not.” You lose a lot of authority in their eyes. If your time isn’t in-demand, your product must not be, either.

To avoid this, stop mentioning how busy your prospects must be. Come out and ask for their time instead.

Here’s a revised CTA:

“I have some recommendations around X. Are you free at [time] on [day] to discuss them?”

6. Using wishy-washy words

Words that weaken your statements will make you seem less confident. To illustrate, here’s a watered-down line:

“I think your company may be able to benefit from [solving X, doing Y].”

Using “I think” or “may” would be fine, but both in the same sentence sounds like you’re totally unsure.

Read through your email for wishy-washy language like:

• “Just”
• “Maybe”
• “Potentially”
• “Might”
• “I think”
• “I believe”
• “I’m guessing”
• “I suspect”
• “I have a hunch”
• “I’m not sure, but …”
• “I could be wrong, but…”
• “It’s possible that …”
• “There’s a chance …”

Remove these terms when possible. Obviously, you don’t want to make promises you can’t keep or statements you can’t back up -- saying “You could be losing $20,000 per year” is preferable to “You’re losing $20,000 per year” unless you can definitively prove the latter.

7. Writing in caps

You might be confused by this point: Doesn’t using CAPS LOCK make your message (and by extension, you) seem more important?

In fact, it does the opposite. Capitalizing entire words comes across as overly aggressive -- as though you don’t trust your message to sound urgent on its own.

Compare these two email subject lines:

• How ReadQ can hire engineers 3x faster (URGENT)
• How ReadQ can hire engineers 3x faster

Which would you be more likely to open? Probably the second. It seems less spammy and more legitimate.

There’s almost never a justifiable reason to use caps lock in a sales email, so pretend this button on your keyboard doesn’t exist.

8. Sending emails over the weekend

Think you'll save your prospecting 'till the weekend? Think again. Sales pro Jeff Hoffman warns, "The only thing a lead or prospect will think when they see your email arrive in their inbox at 10:30 a.m. Sunday morning is that you’re not successful enough to enjoy your weekend free of work." He continues, "And why would they want to work with an ineffectual rep?"

While email open rates and click-through rates over the weekend are historically low, that doesn't mean you should take advantage of an empty inbox to reach out to your prospects.

Hoffman puts the last nail in the weekend prospecting coffin saying, "You also risk them thinking your email was sent by mistake, as part of a mail merge or email campaign, which removes their obligation to respond."

9. Following up too quickly

When conducting email outreach, it's important to get your cadence just right -- and make sure you're sprinkling in a healthy number of calls and voicemails as well.

Sales expert Jeff Kalter warns against following up too quickly, however, "Equally dangerous to your sales outcomes, is to communicate with contacts nonstop. Such outreach is unlikely to meet your prospective customers’ needs and can also reek of desperation."

Desperation will immediately turn your prospect off. Instead, take a scientific approach to call cadence timing and touchpoints. You can find more of Kalter's tips for the perfect sales cadence here.

When it comes to sales, fake it until you make it. You might be a brand-new SDR or a recent hire and nervous behind your computer screen, but there’s no reason your prospects have to know that. An assertive email will help you capture their interest, build credibility, and down the line, win the deal.