How People Judge You Based on the Emails You Write

How People Judge You Based on the Emails You Write

Forget about spinning articles and directory listings.  If you want to effectively market your business online, you need to become an expert at networking with others in your niche.

But there’s a problem: Inboxes have turned into out-of-control monsters. People are increasingly being ambushed with unwanted messages, and they’re getting less timid about hitting the delete key when faced with unsolicited emails.  Often, you have only a few seconds to make a good impression.

So how can you rise above the din?  The recipient of your email will ask (perhaps subconsciously) three questions about you when deciding how to respond.  

I’ll admit these questions are a bit judgmental.  That doesn’t mean someone whose emails aren’t up to snuff deserves to be shunned electronically.  It just means you need to be aware of how your emails sound to recipients who are forced to make snap judgments in order to prioritize their overflowing inboxes.

So if you want to increase your chances of getting a response from a complete stranger, make sure you pass these three tests:


Question #1 – Can You Write Well?

It may sound harsh, but most people don’t write very well.  So when a well-composed outreach email comes across my inbox, I immediately take notice.  Why?  Because I assume someone who can write well is also smart, ambitious and worth investing the time to connect with.

I can’t think of anything more intimidating than trying to write a blog post on how to write well.  The topic merits its own book or even library.  But here are a few things to keep in mind:

Get the Basics Right

It goes without saying, but punctuation, grammar, spelling – all of these are really important.  Brush up on the correct usage of then/than, they’re/their/there, it’s/its, your/you’re and all of these commonly misused words.  I realize I sound like an overly pedantic eight-grade English teacher, but most of the people you’re trying to connect with to help grow your business will notice these kinds of things – good or bad.

Be Anal About Proofreading

You only get one chance to make a first impression, so don’t botch it.  Proofread your emails if you’re reaching out to an important contact for the first time.

If you’re anything like me, you’ll re-read some of your drafts and find egregious spelling mistakes, misused words and incoherent thoughts in what you thought was a well-written first draft.  So take the time to double- or even triple-check your work. (Pro tip: It helps to read your message aloud. You’ll quickly hear the awkward parts.)

If you tend to read through your sent email looking for typos – and I KNOW others do this, too! – you’re on the right track.

Ditch Text Shorthand

Surprisingly, “lol” doesn’t exactly translate to “laughing out loud.”  In email speak, it means “please take my email much less seriously.” Including half a dozen emoticons in your email has the same effect.

Think About Tone

Tone can be tricky to express with an email, given there’s no face-to-face interaction.  You want to be friendly and upbeat without coming across as overbearing or unnaturally exuberant.

You can use exclamation points, but do so conservatively and only after sentences that merit them. If you must use the smiley face (which can sometimes be a way to lighten an otherwise serious sentence), make sure you limit it to one per email.

Don’t Skimp on Capitalization

if you don’t capitalize when you should, i guarantee you will rarely get replies.  not capitalizing the beginning of your sentences simply makes you look lazy. Don’t do it.  Embrace that shift key.

Pick a Professional Email Address

If you’re still rocking your email address from the ’90s, it’s time for an upgrade.  Anytime I see an email address for one of these dated domains, I instantly think the person I’m corresponding with isn’t too tech-savvy.  It may not be a fair judgment, but given that I have about 30 seconds to make the call, it’s the assumption I (and others) settle on.

You should have an email address from,, or from a business domain.  And make sure to keep it clean with a variation of your first and/or last name.  If I were using my old high-school email address for outreach – – I doubt I’d get many replies.

A few other tips to follow

  • Keep it short!  If it’s more than 10 sentences, you’ve written too much.  Six to seven is ideal.
  • Don’t be overly personal.  Bearing your soul to me in a first email is awkward and inappropriate.
  • If your text color is anything other than black, change it back.
  • Stick with a standard, professional font (i.e., no curlicues).

Again, I realize it’s nearly impossible to cover the fundamentals of good writing with a few bullet points. It really is a life-long pursuit.  And much of this is as much related to formatting as to actual writing.  But these guidelines will go a long way toward making your emails count.

You should be able to find loads of information about upping your writing game, including this great piece from Forbes.  (And if all else fails, you can always marry a writer/editor. That’s what I did!)

Now that I’ve convinced you that I’m actually a cranky, 80-year-old English curmudgeon, let’s move on to the second question your recipients will ask.


Question #2 – What Do You Want?

If you’re writing an outreach email, you almost certainly want something specific from the recipient.  The problem is, what you’re asking for is extremely valuable – that person’s time, attention or their audience –and they don’t know you.  Why should they spend their finite resources to help you, a complete stranger?

That’s why the best approach isn’t to ask for anything.  Instead, make your goal just to start a conversation.  If you’re a quality person offering something of value, the option to work together will naturally come up in subsequent emails.  And it makes it much more likely someone will reply to you if you don’t ask for anything up front.

I’d never interacted with Greg Ciotti from HelpScout and SparringMind when I received his first outreach email:

Hey Andrew,

Greg from Help Scout (and Sparring Mind) here. I’m one of the few contributors to the Shopify blog along with yourself, and I’ve been digging what you’ve been putting out lately!

This is just one of those emails where I reach out to somebody doing real stuff, heh. 🙂

But seriously though, keep up the great work my man, looking forward to what you come up with in 2013, and if you’d ever like to collaborate, give me a holler.


I’m guessing Greg’s goal in reaching out was to eventually get HelpScout additional exposure via the eCommerceFuel brand.  And yet, there’s no hard pitch.

Instead Greg makes a connection, offers some praise of my work, tries to genuinely connect with me and proposes an open-ended collaboration opportunity that doesn’t require an immediate commitment.

And did you notice there was only one exclamation mark and one smiley face?  Tone nirvana.

Like an expert hunter stalking his prey, Greg executed the cold approach perfectly.  Since then, I’ve recommended (awesome help desk software) to dozens of people and had Greg on the eCommerceFuel podcast to talk customer service.  So I’d say his email did the trick.

Another great example from this week via Jeff from

Hi Andrew!

I just wanted to tell you thanks for your podcast each week. I listen all the time. You have great guests and good discussions. I actually run my own ecommerce store that has been an awesome ride so far. I’m no expert, but have some experience in the ecommerce world.

I would be happy to help you out if you ever have questions. Keep up the good work!


Jeff’s email asked for nothing; he was simply writing to let me know how much he enjoyed the podcast and even offered to lend his experience to help out.

When I viewed his website,, I was blown away by an impressive product and a beautifully executed design.  We started a discussion, and I’m hoping to have him on the podcast in an upcoming episode. (Although he doesn’t even know it yet.  Jeff, I’ll be in touch!)

Did you notice the tone?  An exclamation point in the header and one in the body.  Friendly, but not over the top.  You may think I’m over the top with my nitpicking, but these small things can make a big difference in how an email is received.

Focus on building a rapport, and you’ll usually see long-term benefits if you’re doing something worthwhile that can genuinely help the other person.


If You Must Ask for Something …

If you have to ask for something in your initial email, make sure you do three things:

  1. Show you’ve spent time on their site
  2. Offer something that would be valuable to them and
  3. Close with an authority builder


Here’s the wrong way to begin an email:


I’d like to write a guest post on your blog about scorpion-taming kits.  We sell dozens of scorpion cages on our store, and I know a lot about them.  All you’d need to do is give us a link back to our site and we’d be happy to write this for you.

Thanks, Andrew

About the only thing this email has going for it is brevity.  It fails in just about all other aspects. Where’s the rapport building?  The offer that’s of interest to the site owner’s needs?  And why should they trust you (er,  me)?  Here’s a better example:


First off, I absolutely love your site on scorpion taming – really well done.  Especially like the video you had on teaching them to do backflips.  Didn’t even know this was possible!

Writing because I noticed you don’t have any posts or articles about scorpion cages.  If it’s something that your readers would find valuable, I’d be more than happy to write a unique, quality post for your site.  No commitments from your end – if you don’t think it’s top-notch stuff, there’s no obligation to use it.

I’ve been selling scorpion cages online at for the past four years, so we really know the industry.  If you’d like to see some of the resources we’ve compiled, you can do that here.

If this isn’t a good fit for your visitors, not a problem.  Appreciate the consideration and nice connecting!

– Andrew

Quite a difference, eh?  A lead that shows I’ve actually spent some time on his site and am not spamming him with a fill-in-the-name outreach template.  An offer for content that puts his visitors at the center of the value proposition and gives him an “out” if the content is low quality. And, finally, an authority-building bit at the end listing my credentials and showcasing some of the top-notch work I’ve already created.

As I said earlier, the best type of outreach email simply starts a discussion. But if you’re going to pitch right out of the gates, make sure your email focuses on their needs and not yours.


Question #3 – What Have You Done?

If you’re asking for something meaningful from the recipient, there’s a cost (or risk) involved in them agreeing to it.  Whether or not they accept depends on how well you present yourself (how you write), your offer (what you’re asking for) and your track record online.

The biggest indicator of future behavior is past performance, right?  So when evaluating requests – especially larger ones – people will often do some sleuthing about you.

Meet Rapportive.

Rapportive is an insanely useful plug-in for Gmail that automatically pulls data on anyone who sends you an email from websites like LinkedIn and Facebook.  You can see at a glance what they look like, where they’re from, the websites they’re affiliated with and all of their associated social media accounts.

Listed below is the Rapportive profile report for Erik Bandholz of, whom I had on the podcast recently.  As you can see, the Rapportive profile includes a picture with his glorious beard, his hometown of Spokane, WA, the name of his company and links to his LinkedIn and Twitter pages.


I’m using Rapportive as an example because it consolidates a number of biographical resources into one place, but the following tips apply just as much to a simple Google search someone could do on you.  Here are a few things you should consider about your online history in Rapportive or elsewhere:


There’s something comforting about seeing a person’s real picture pop up in the Rapportive box and/or social media profile.  Conversely, it feels a bit strange when a question mark pops up where your headshot should be when no picture is available.  If at all possible, make sure your mug is on display by updating your LinkedIn, Facebook or Gravitar headshot.

Websites & Blogs

Make sure any sites you want others to see are listed in your LinkedIn profile so they come through on the Rapportive feed, especially if they can’t be inferred from your email address or signature.  You don’t need to have a seven-figure eCommerce store up and running, but having a blog post with some well-written posts – or even a nicely done profile page – goes a long way.


Of all the social media accounts I use to get a feel for someone professionally, this one’s the biggest.  I don’t necessarily care how many connections you have.  But do you have a profile with a headshot and details that give me some sense of your professional background?  If you can’t be bothered to add a photo and some relevant work and/or school history, it always raises a flag.


A lot of people don’t use Twitter, and up until 18 months ago I didn’t really see the point either.  So it’s not a big deal if someone doesn’t have an account here.  But if they do, I always look at the number of people who follow them relative to the number of people they follow.


If someone has 25,000 followers but follows 30,000 people, it’s not that impressive.  It’s easy to get followers by following random people and having them follow you back.  But if someone has 25,000 followers and follows only a fraction as many people, you know that person’s audience was likely built on him/her saying or doing interesting things.

So what’s the point of all this?  If you’re attempting to network with influencers in your niche (and ultimately benefit from their position), you need to build credibility.  If there’s no trace of you, your company or your work online, you’re going to have a much harder time doing that.

Install the Rapportive plug-in in Gmail, send yourself an email and see how YOU look in the profile.  Does your smiling face appear with links to your work and online profiles?  Or does it look like there’s no record of you anywhere?  You can see how stark the difference is in the example with Ryan Barr from below:


You might be saying to yourself:  “I don’t have a lot of Twitter followers.  Or a great store.  Or anything, really.  I’m just starting out.”  Fair enough!  Everyone started somewhere.

In that case, you need to build something you can refer people to as a credibility booster.  It could be half a dozen really great posts on your new store’s blog, even if you know very few people will read them.  Or a video series that showcases your expertise on a topic.  All that matters is that it’s high-quality and you can leverage it to build credibility.

But you need to be willing to invest the time to create it before beginning any serious outreach campaign.

It Doesn’t Have to Be Perfect

This may seem like an intimidating number of rules to follow, but don’t let it scare you.  You don’t have to write flawlessly to get results.

In fact, after writing this post specifically on writing mistakes NOT to make, my wife sat me down after editing it (wasn’t kidding about that marrying a writer thing) and had a talk with me about the difference between its and it’s.  Apparently I misused the two even after lecturing about it above!

There’s a good chance you even spotted a few typos above as well.  So perfection isn’t the goal – attentiveness is.  Just keeping these rules in mind will set you head and shoulders above other messages in the inbox.

Are there additional ways you evaluate unsolicited emails?  Think I’m an email elitist who needs to chill out?  Or just have a comment or question?  Let me know in the comments below.

Andrew Youderian
Post by Andrew Youderian
Andrew is the founder of eCommerceFuel and has been building eCommerce businesses ever since gleefully leaving the corporate world in 2008.  Join him and 1,000+ vetted 7- and 8-figure store owners inside the eCommerceFuel Community.

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44 Comment

sunnayJanuary 22, 2014

Andrew been following you for a while, great blog, love how your break it down and show how its done. Cheers and keep them coming, look forward to your next post.

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Andrew YouderianJanuary 22, 2014

Thanks Sunnay!

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JustinJanuary 22, 2014

Great post, Andrew!

Don’t you love it when you open an email and the sender just absolutely nails it? I’ve always been a bit anal when it comes to reaching out via email (left over from my corporate days, I think) and so I really apppreciate it when someone has obviously taken the time to understand me, my company, etc.

Double thumbs up for Rapportive, too. The tool has really helped me keep track of who I’m emailing back and forth with (I leave short notes) and you’re right, it’s really nice to see the picture of the person you’re emailing. It DOES feel a little stalkish at times though, eh?

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Andrew YouderianJanuary 22, 2014

Thanks Justin! Yep, few things are as nice as getting a beautifully crafted outreach email in your inbox.

Rapportive can feel a little bit stalkeresque at times. Sometimes I’ll mention something in a reply that I learned exclusively about a person from Rapportive (vs. their email) and I always wonder if that freaks them out a bit. 😉

Hope all is well at EmpireFlippers!

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Billy MurphyJanuary 22, 2014

Can you give advice on marrying editors? That would save me a lot of time. Thanks!

Love the beardbrand email, hope you sent it!

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Andrew YouderianJanuary 22, 2014

My fool-proof strategy:

Initiate lots of discussions about grammar and how you just can’t STAND how people misuse semi-colons. Subscribe to The New Yorker magazine and leave issues lying around your house. When she asks about it, nonchalantly say:

“Oh that? I’ve been reading it for a few years now. It’s not quite as good as it use to be, but it’s not bad. I just wish they’d take out all the cartoons.”

Mix this formula with a healthy dose of foot and backrubs and you’ll be engaged within six months.

Good luck! 😉

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JayneJanuary 22, 2014

Hi Andrew,

Not sure how I landing here, but I’m glad I did. What a useful post. I’m about to start prospecting for work so this was perfect. Great stuff.

Thanks so much.

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Andrew YouderianJanuary 22, 2014

Glad it helped, Jayne! And thanks for swinging by the site.

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ChrisJanuary 22, 2014

Great tips Andrew!

One thing that has helped me avoid email typos is the Gmail Labs option “Undo Send”. It gives you about 30 seconds after sending an email to stop the email from going out. This really forces you to give your email one last focused proofreading and has saved me time and time again.

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Andrew YouderianJanuary 22, 2014

Good tip! Yeah, it’s frustrating when you re-read 15 seconds after sending and have a face palm moment. I’ve done that a ton of times.

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Mark MathsonJanuary 28, 2014

Good tip Chris on the Undo Send Labs app. Will have to check that out.

Something I’ve gotten into the habit of and it works really well, is to start composing the email with the Subject and Body of the email, *before* you put in the recipient in the To or CC field. Saved me many times!

Great article Andrew, as always!

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Patrick BrennanJanuary 22, 2014

I think a lot of us get caught up in the “fury” of emailing & forget what a difference personalization, thought, and intent can make in a simple email message.

Thanks for the great article!

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Andrew YouderianJanuary 22, 2014

Very welcome, Patrick!

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Wendi MakuchJanuary 22, 2014

Hey Andrew,

LOVE this post! Especially the part about “read it out loud.” This is something I’ve been doing for years so thanks for the validation.

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Andrew YouderianJanuary 27, 2014

Thanks Wendi!

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Carole @ Rustic ArtistryJanuary 22, 2014

I keep an Evernote tab for email templates that I think are good. Mostly I’ve been adding marketing emails to it, but I’m going to add good personal emails like your examples above as well. Should save a lot of time when I’m trying to craft my next email to connect with a blogger.

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Joe MagnottiJanuary 22, 2014

If you use Gmail, try Canned Responses which you find under Labs in settings. No more copy and paste!

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BrianJanuary 22, 2014

Hey Andrew,
Always enjoy your work and thoughts! I think the email etiquette you shared can apply to multiple areas of life 1.) Be professional 2.) Tactfully get to the point 3.) Live up to your credentials and be true.

One extra idea that has helped me is to use the 80/20 principle on the content portion of the message. Basically, after the first draft of an email cut the body of the note down to include only the highly valuable thoughts. Waiting a day between writing and sending has helped me identify the stuff to cut out.

Also, I personally try to keep the nice fluffy comments (fat) to ~20% of the total email. I just learned that 18% human body fat is healthy and maybe that applies to emails too!
Keep on Rollin!

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Andrew YouderianJanuary 27, 2014

Good tips, Brian! Yeah, we usually include way more than we really need to.

Thanks for sharing.

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JackJanuary 22, 2014

Most of what you wrote in this article is really good. The one part I would somewhat disagree with is that you assumed:
1. The e-mail recipient uses social media often, and as a resource to find out information.
2. That the recipient thinks that what is on social media is important.

For many people, particularly older people, both of these assumptions are incorrect. Many adults use Facebook only to connect with friends and family if they use it at all, and do not use Twitter and LinkedIn at all.

If they want to find out more, they are more likely to use a Google search and Better Business Bureau or Yelp.

I also wonder about the value of a picture (in LinkedIn &/or Google Authority if you are an older person or not that good looking, trying to sell to younger people, or if the people you are e-mailing are likely to be much younger than you.

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Max Saint-FestinJanuary 22, 2014

What an insane coincidence, I was just about to send an email to a merchant when this popped into my inbox.
This is really useful stuff, and I’ve included many of your tips in my email. I like it because it gives people a way of looking professional & big, even though they may be a one man operation.

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Andrew YouderianJanuary 27, 2014

Glad it helped, Max. 😉

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Joe MagnottiJanuary 22, 2014

Great article Andrew, now I would like to see one on forum posts. First rule, no trolling! 😉

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Andrew YouderianJanuary 27, 2014

Thanks Joe!

Good idea on the forum etiquette post. There’s this broker guy in the eCommerceFuel private forum (Empire something or other) who is always lighting people up with incendiary comments. Classic troll. Maybe I’ll write a post for him…..

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Annie BarnesJanuary 23, 2014

Hey Andrew,

I’ve been following you occasionally and I really enjoyed this post. It’s very informative, well written, and I certainly learn something! Thanks for the tip on the Rapportive plugin.

I’m a newbie and I look forward to learn more from you 🙂

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LeightonJanuary 23, 2014

Fantastic post, Andrew! I love what you were saying about reaching out initially without asking for anything. I’ve noticed that that makes a big difference in the email and relationship being well-received.

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Andrew YouderianJanuary 27, 2014

Thanks Leighton! Yeah, I’ve found it makes a bid difference too.

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Aleksejs IvanovsJanuary 23, 2014

I didn’t think it was intimidating at all, I think for the most port – only the first two big points were needed to cover the whole topic, would you agree, Andrew?

Thank you, and good job on getting a writer, wife!

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JiembJanuary 24, 2014

Thanks Youderian!!!… 😉 LoL. I feel like their is soooo much that I can learn good. I reely hope that you’re wife can teach me how to do better in writing.

On a serious note, thank you for a great post. I can’t help but feel that in some ways it was written for me. I appreciate you and your unmatched focus to quality and the growth of your followers. We are all better for having you in our life. You are a dear friend and a great man, keep it up!


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Andrew YouderianJanuary 27, 2014

Thanks Jimbo! Looking forward to playing some more hoops next time you’re in Bozeman!

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Top 25 Inbound Marketing Articles of the Week: January 24, 2014 – UpCityJanuary 24, 2014

[…] email. Whatever you include in your email reflects on your brand and how the customer receives it. Andrew Youderian shares this lesson in a detailed […]

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NickJanuary 26, 2014

Great article. I really enjoyed reading your e-book and always look forward to new content. Keep it coming!

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Shehzad JiwaniJanuary 26, 2014

Great post Andrew; well written with practical tactics.
I’ve been following you for a while and I enjoy each of your articles.

I just want to quickly point out a small grammatical error in your writing. :-p

Under the heading “If You Must Ask for Something”, the second point should read:
Offer something that would *be* valuable to them and

Oh the irony. Haha!

I look forward to your next post sir.

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Andrew YouderianJanuary 27, 2014

Shoot! I thought I had escaped, but KNEW there was an error in there somewhere.

Thanks for giving me a dose of my own medicine. Off to correct it now….

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Lorraine RorabaughJanuary 30, 2014

Thanks for the insightful post Andrew. I’m always searching for ways to pitch our products without being to forward about it. Look forward to the next post.

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Denis De OFebruary 7, 2014

Again, thank you very much for great info. I do have English’s issues as it is not my first language.

I will get better every day and specially when I see information like yours.

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Dan @ Feeless LeaderMarch 2, 2014

Good stuff Andrew!

Showing that you actually took the time to research whom you are going to be email is key. I hate getting emails that are a copy & paste blasted off to 593 other people.

Along with Rapportive, I use Yesware. It’s a free add on for gmail that allows you to track if your email was opened, where it was opened, if the end user click any links, it has built in CRM, canned responses, etc… It’s a pretty killer tool.

– Dan

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Steve DaarMarch 6, 2014

Thanks for posting those example emails from Greg & Jeff – – really good stuff to model.

Also can’t stress enough keeping that first email short!

– Steve

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rajashreeApril 16, 2014

Hey Andrew,
Nice one. Enjoyed reading it..and after reading the blog my first action was I uploaded a profile pic of mine in my email account.

Thanks and best wishes

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C O AMay 1, 2014

May seem judgmental to some, but then I do judge others based on their e-mail compilation skills.

If I wish to respect a vendor, then surely s/he must know basic English grammar if s/he is worthy of my custom.

And surely in this era, and reasonably educated person should have base knowledge of Standard English.

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Lori AlbrechtOctober 4, 2015

This is very informative and sheds a new light on sending email at my job. Thanks!

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