Don't Send Yet! 9 Email Mistakes You’re Probably Making—And How To Fix Them

Are your emails too long? Too short? Sent to too many people? Or at the wrong time? Learn how to say exactly what you want—without annoying those on the receiving end.

Email. The bane of your existence, a tool that seems to define many of your waking hours, a mode of communication invented only two decades ago.

We all use it, some of us love it, and many of us dread it.

There are plenty of tips and tricks about making email more efficient—using specific tools like boomerang, limiting yourself to certain hours per day and chasing the dream of inbox zero.

While email efficiency is a dream—hacking these communications systems can only take us so far. Important, too, is hacking yourself to become a better writer so you get more of what you want through email.

Are your emails getting the results you want?

When you improve the way you write and learn how to design better messages, you will resonate with the reader, improve sharability, and increase the bottom line.

Last week, I caught up with writer, designer, and strategist Sarah Peck, who teaches workshops on developing effective communication skills. We talked about using email to get more of what you want and what mistakes everyone is making in this commonplace communication form.

Here are nine common mistakes you might be making:

1. Sending emails only when you need something.

The best time to build any relationship is before you need something, not waiting until the moment you need something. A friend of mine gets into the habit of sending five thoughtful emails each Sunday night to check in with people who he likes, admires, or thinks of. An email might look like,

Hey, saw some great news about you—just wanted to say congratulations! I love watching what you’re up to through my various news feeds, and I wanted to send a note to say how much I hope you’re doing well.

It’s a great way to remember to reach out to folks you want to be in touch with, and an actionable way of practicing gratitude.

2. Forgetting that there’s a person on the other side of your email.

Just as you wouldn’t walk into a friend’s house for dinner and bark out a command, often those little niceties in the intro and end of a message can go a long way. Social cues aren’t dated constructs; they’re valuable warm-up phrases in communication. Start by saying hi, comment on someone’s latest achievements, and wish the other person well.

Hey stranger! It’s been a long time. If Facebook’s telling me the scoop, it looks like you had an eventful Spring…congrats on all of your successes!

3. Using the first person too much.

Many emails—and essays—are written exclusively in first person. Shift the focus to the recipient and consider what they want, need, or would like to hear. After writing an email, scan it quickly for how many times you use the word "I." See if you can edit some of them out.

For example: "I’m teaching a new writer’s workshop this Spring, and I want help sharing the program. I think you’d be interested in it" (all "I" statements) can be turned into:

Hey, Leslie. A while back we chatted about ways to improve your writing skills—I wanted to reach out about this writing workshop for creatives that’s just launched. I thought you might enjoy taking a look. Let me know if this is what you were looking for.

4. Sending the email at the wrong time.

Just because you’ve written it now doesn’t mean it needs to be sent at this exact moment. Delaying the send is one of the most powerful and underutilized tools of emailing.

Evaluate whether or not the message is urgent and needs to be replied to immediately. If you’re cleaning up your inbox during your scheduled time, fire off the messages that are urgent and consider sending messages in the morning.

Scheduling emails to be sent in 24 or 48 hours gives you (and your clients) space to breathe between nonurgent projects, and it also sets up a rhythm of communication whereby your client no longer expects you to reply instantaneously. The more structure and parameter you give to the form of your messaging, the easier it is for the client to learn what to expect. You can either train someone to expect instantaneous answers at all times, or to learn the rhythm that’s best for you and your business.

Then, in the case of an emergency, if the client emails and you need to solve the problem straight away, you can send a quick message late in the evening or on a weekend. In this scenario, you become the hero to your client.

5. Sending to too many people.

More recipients in the "To" field does not mean that you’ll necessarily get more answers. In the age of digital marketing, people who blast messages in broadcast form without understanding who is in the "to" line can erode their chances of a message being opened. A perfect email is one that’s sent to exactly who it needs to go to, with a specified desired outcome.

The more specific you can be about who you ask, the better. Asking everyone in your network is bound to get you a bunch of silence in our overconnected world, or unsubscribes and un-follows across your various platforms. It’s better to ask three people who are very well equipped to answer your query than 15 people who aren’t interested at all.

The more specific you can get about who should be receiving the message, the better. One direct ask that results in a yes is better than asking 50 people who don’t respond (and spamming their inboxes).

6. Knowing nothing about the person receiving your email.

Do your homework on the recipient. One great tool to glean fast information about who you’re talking to is Rapportive, a sidebar that lets you see the latest public posts (and a picture) of the person you’re communicating to.

7. Forgetting to send updates or interim messages.

If you’re waiting for an important message from someone, the time spent waiting for a delivery can seem interminable. If there’s a long delay in sending an item that’s highly anticipated or expected, or you’ve experienced a few hiccups—send a one-liner email to update your receiver on the status of the project. You’ll know that you need to send a quick note when you start to get anxious about not delivering or they seem to be a bit flippant.

Sample copy:

Hey, Sarah. Just wanted to send a quick update about the delivery of our proposal. We’re set to get you something by next Friday, but we might be a few days early. Talk to you next week! Let me know if you have any questions in the meantime.

Hey, Sarah. I know we touched base last month and I’ve been far too slow in getting back to you. I’m still working through the pile on my plate, but I should have something in the next 2-3 weeks. Didn’t want to keep you guessing! Talk soon,

8. Making messages too long.

Depending on the nature of the message, emails can vary from a few words to thousands of words. The longer the email, the less likely that someone will read the entire thing. Long emails generally mean that a larger strategy, framework, or document might be in order. Some companies shift to using four-sentence emails and linking to longer pieces of work through Google Documents, Asana, or Basecamp (or other project management software).

9. Using email exclusively.

Efficiency does not necessarily mean one single system. Often, redundancy in communication can be extremely helpful, as each tool (video, chat, email, Skype) adds a layer of human nuance back into the correspondence that’s happening. Laura Roeder’s digital marketing team is distributed across multiple countries, and in order to stay in touch (and in concert with each other), they focus on "over-communication," through the use of multiple tools at once.

Now: Four ways to focus on writing better emails:

Tell sticky stories. Everything makes more sense with an illustration. Highlight and example, illustrate an ideal customer avatar, or tell a specific instance of a problem you had. Setting the context and the stage (that seems obvious to you, the writer), makes it easier for people to understand the pain point, the context, and the reason why you’re writing. When people can see your story—who you are, where you come from, why you’re doing what you’re doing—it’s easier for them to become a part of it.

Use the four-sentence, one-link rule: Keep your email to under four sentences (or five!). Focus on the pain point or problem you’re solving. Limit yourself to only one link. If you have to, make that link a document.

Be responsive and reflective: Observe how others communicate and adapt your style to meet them midway. Customize your communication by mirroring the style of a received message. Does someone send short messages with formal addresses? Respond in style.

Bookmark emails that you love with Evernote. Use the vast number of emails in front of you (and in your inbox) as clues to great messaging. Watch what emails you open first and are most excited about. Create a few folders in your mailbox system for great introductions, sample short messages, and thank-you notes that you like. Keep these for future use if you’re ever in a bind. In any art, there’s no need to reinvent the wheel—and paying attention to great writers (and what we personally enjoy) is a great way to get started.

Email is our number one form of communication, which means that everyone is a writer. The most powerful thing you can do in both your personal and business life is learn how to write well and tell great stories. Messages that persuade, content that converts, and language that inspires action are critical for getting what you want.

If you’re looking to get more of what you want out of email (and writing), check out Sarah’s Writer’s Workshop.

What about you? What email mistakes do you see people making all the time that you wish they would fix? What’s the greatest email you’ve ever received?

[Image: Flickr user Martina Photography]

Add New Comment


  • Avery Mist

    Thanks for the post. Really interesting.

    But Rapportive is acquired by Linkedin and they are limiting the service to linkedin profiles only. I searched and found an excellent and better alternative named Vibe ( . Highly recommended to use.

    Have Fun.

  • Benjamin Boyer

    Everyone Loves hearing good news and making new connections that are real.

    Keeping messages short sweet and simple combined with occasional introductions and fun / funny comments can make emails something to look forward to because there is either some kind of value or a smile just about everytime

  • Cheric

    In this Smartphone world, emails should have a specific purpose with specific actions required from specific people. If your email has no meaning the first time to someone, the chances of them reading anymore or responding in a timely fashion to further emails fade quickly. In general:
    - I think most people should avoid the exclamation point as much as possible. Nobody is that excited about the subject matter.
    - Too many people in the CC - who really needs to be cc'd?
    - Reply all with "go team!" - Super annoying
    - Not spell checking before pressing send
    - Not being aware of who all is in the email chain - Look before sending
    - Using bullet points helps in staying on point and keeping emails short

  • Terry Stidham

    Amber, Thanks for the tips. On you #3 tip why not take "I" out completely and say ... "Wanted to reach out...". and "Thought you might..." instead of Hey, Leslie. A while back we chatted about ways to improve your writing skills--I wanted to reach out about this writing workshop for creatives that’s just launched. I thought you might enjoy taking a look. Let me know if this is what you were looking for.

  • mmcfee

    Because that's, at best, colloquial speech or, at worst, it implies you're too busy to type a complete sentence; It's brusque, not to mention grammatically incorrect. I'd go so far as to say it reads like a dictate or instruction list, not a 1:1 communication.

  • Paul H. Burton

    I LOVE the sender-centric discussion! Everyone wants to solve the 'email problem,' but no one wants to  acknowledge the fact that "they" are "we." 

    I've spent the last eight years helping people process email better - receiver-centric thinking. Six months ago, I launched my latest seminar - "Send: A Dozen Ways to Make Email Productive Again" - - and co-founded a new company - RepriseMail ( - to address the sender-centric issue. Both of these efforts focus on what individuals can do to lower the level of email noise we're all creating. Think of it as the "reduce" part of reduce-reuse-recycle.Email is a wonderful tool. Moreover, it's become the lowest common denominator for communications worldwide. In fact, email use is projected to grow 13%/year until at least 2016. Sure, other communication technologies exist and some people have made good use of them. But what do we do right now about the billions of messages being created today, tomorrow and the next day?We MUST shift our focus away from how to handle messages better and direct it towards how to create them better. This article, and the other resources that are just coming of-age, attack the problem at the point of origin. They focus on curing the disease instead of treating the symptoms.Who else will join the battle?

  • JamesFDJohnston

    How about having an image for your signature? Looking for an email with an attachment and you have to rely on impeccable subject lines because every email from said person has an attachment...

  • Jeff

    I read every comment for this except Paul's. And then I laughed because that's exactly what happens in email--the short ones are more likely to be read.

  • Shannon Callarman

    I can't tell you how many emails I receive from people just looking for something. The emails always sound awful: "Hey! How are you? Hope all is well. So I'm looking for a job, is your company hiring?" It makes me cringe. Always send emails just to keep in touch and say hello before asking for a favor. 

  • mmcfee

    Agreed. Unfortunately this is exactly what #2 implores you to do: "Make forced chit-chat before you get to the point". Of course, this same advice is given all over, so it's not just this essay that's guilty of promoting it. 

    I disagree with #2 for the very reason you've outlined here... everyone knows it's insincere. If you don't have an actual social relationship with the person, don't pretend to one in an email requesting something of them. If you do have such a relationship, it's not necessary, unless you're a bad friend who doesn't communicate otherwise. 

    Most of the people who email me requests are not my friends, so I don't expect them to pretend to be or to butter me up. The former is disingenuous and the latter is time-wasting.

  • Shannon Callarman

    I definitely see where you're coming from! But there's a big difference between being fake and having common courtesy. Just today, I had a PR gal email me about guest blogging for my company. Her first sentence was welcoming and it made me want to read her email and respond right away. It went something like "Jenny from [company] here! Hope you're doing well. Can't believe it's already Wednesday". Then she got straight to the point why she was emailing me. It was perfect! 

    But compare it to an email I received a few weeks ago. It went something like this:

    "Hey, long time no see. Are you still living in [city]? So, I'm trying to find a place to display my artwork. Know anywhere? Let me know. Thanks" 

    And when I responded politely that I'd keep her posted, even though the email bugged me, I didn't receive a response. It was cheap. 

  • Stéphane

    I like the idea of 4 sentences, one link (or picture).
    However, sending emails just to say "hi"? - No way! People have enough clutter in their in-boxes and it's not the way to build relationships with your colleagues. Go to see them or pick up the phone or write a snail-mail letter, all of which are far more personal and thoughtful than email.

  • Valentina Razionale

    Worst mistake ever: sloppiness. I happen to receive emails in which the font or color changes from line to line: how can the sender NOT notice? Don't they proof-read? And if they notice and don't bother to fix it, it's even worse, like they think the receiver is not worth presenting a tidy email. Second worst type of email: the one full of grammar errors, or written in the same style you would use in a text to a friend, or a chat with your pal. Even if we are in "friendly" relationship with the person we are writing to, it's still work nonetheless, so I expect a well constructed email with correct sentences, punctuation, etc. 

  • Amber King

    Thanks for these tips Amber. Emails that are too long are not something I am happy to read. Keep it short and concise so that you won't waste each others time. 

  • Helenlai143

    I think the writer or editor ignores one foundamental communication principle, they put all the text in all caps which is a pain to read. People who teach others how to communicate should not be like this.

  • Emily

    Great article Amber !
    One thing that some people do not understand, is how to use: BCC. I prefer not to have my email address shared with someone sending me an email. Most people probably prefer to maintain their privacy.
    Thank you,
    Emily Romaine