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Create Effective Outreach Emails That Won’t Get You In Trouble

It’s tricky, isn’t it? Knowing the best way to reach out to people who can help your business grow?

You want to connect with the people you’ve bumped into at business events. You want to tell them what you’re doing, maybe ask them to help out with a share or link to your latest guest post.

So what’s the best way to get through to them to start building a relationship that leads to a joint venture, a meeting of the minds, or an introduction to their audience?

The answer is an effective outreach email strategy.

But wait! Don’t go emailing everyone you can think of just yet.

It’s tempting to think that if you send enough emails to as wide a list as possible—if you load all your business cards into MailChimp—the ones that want to help will reveal themselves.

Sorry, but this won’t work.

Most jurisdictions insist that for someone to be on your automated email list, they must have explicitly and verifiably requested it, usually via a double opt-in landing page or form.

Reputable email services like AWeber and MailChimp will enforce this, and you are quite likely to end up having your account suspended if you don’t comply.

To be effective, an outreach email must be personally written on a one-to-one basis; do not automatically generate these messages and send them out in bulk.

But most people don’t realize that even some individual one-to-one emails get stopped by filters or marked as spam.

Could You be Making This Costly Outreach Mistake?

In most countries, sending an unsolicited commercial email is a criminal offense.

This doesn’t just apply to bulk email services, individual emails are the same. Every day, thousands of one-to-one emails fail to reach their recipients because they are marked as spam—if you use certain phrases in the subject line, if you include affiliate links, or if your IP address or any of the addresses in the header and content of the email is registered on a spam database.

Fortunately, even under the strictest rules and tightest spam traps, you can still use email to connect for the first time.

You just have to be very careful how you do it.

How to Build Trust by Covering All the Legal Bases for Effective Outreach Emails

email outreach trust

Your mission? Reassure your recipients you are one of the good guys.

Remember, for many people, giving an email address is a leap of faith. If you are obviously flouting the law, they’ll be suspicious of your motives.

Sure, you could spend days trying to figure out all the regulations for each country you are writing to.

But frankly, life’s too short!

Most jurisdictions will allow messages with commercial intent to be sent so long as you can prove implied consent and comply with all the legal requirements.

Unfortunately, each country has different ideas about what constitutes commercial intent.

  • Is asking for a link to your blog commercial intent?
  • How about asking for an introduction to a potential client?
  • Sending out an invitation to join your email list?

Because these interpretations differ so much, it’s best to behave as though every country has the toughest rules.

I’m not a lawyer, and this is not legal advice, but following these basic requirements should keep you out of trouble.

  1. Make sure you can prove at least implied consent. If the person gave you a business card with an email address on it or publicly published their email address and has not taken an opportunity to refuse commercial messages, you should be OK.
  2. Be sure the content is either purely informational or is a request for information and clearly relates directly to the business interests of the recipient. It should not come across as salesy.
  3. Identify yourself in a traceable way, visible without opening the email. Do this by using your full name and trading name in the “From” field and using an email address attached to your own registered company domain.
  4. Provide an easy way for the recipient to tell you they don’t want any more messages. To comply with this guideline, I include a statement at the bottom that reads,
 “If you would rather not receive any further email communications from me, please let me know by reply. Rest assured this is an individually created email and is not automatically generated from a list.”
  5. Do not include links to products, affiliate offers, or advertising landing pages. And don’t even think about attaching a pdf!
  6. Use a valid postal address, company registration, and phone numbers in the footer of the email.

Following these general guidelines demonstrates you genuinely want to comply with the law and are not hiding behind anonymity.

Of course, we must ensure the messages actually reach their inboxes, so let’s look at some spam red flags.

Red Flags That Trigger Spam Filters, and How to Avoid Them

By covering all the bases above, you’ve already resolved some of the following. Unfortunately, some of them may have nothing to do with a particular email message at all.

You’re a registered spammer

You probably just don’t know.

You may not have sent any spammy emails, but the IP address of your Internet or email service provider or a link in your email could have been registered with one of the many spam databases.

Organizations like SpamCop and Barracuda collect complaints and automatic updates from victims and spam filtering software.

Unfortunately, they don’t know you are a nice person. Sometimes it’s just that the last person to use the IP address linked to your Internet connection was a bad guy. If you have shared hosting for your email server, one of the other sites may be up to mischief.

Fortunately, you can check this quite easily.

If you have a second email account (maybe a personal Gmail account), send yourself an email message from your outreach account. If not, send one to a friend.

Take a look at the header information on the email. Make a list of the IP addresses (groups of numbers separated by periods) listed in the path that the email has taken to get to the destination. Then check these addresses at If any of them are listed in the spam database, you can email them and ask to be removed.

If your email service provider is listed, choose another.

You look like a spammer

Spam filters look for combinations of words in subject lines and content. Certain keywords automatically trigger the filters.

Avoid using anything other than upper and lower case standard letters. “hEY YoU” looks suspicious.

Once you have been whitelisted or added to the recipient’s contact list, you can be a bit more relaxed. But until then, it’s best to stick to “plain vanilla.”

Excessive use of links

Never include affiliate links in your email.

A single link to your own profile on your website is OK so long as it is properly introduced, but try to avoid doing so until you are whitelisted.

Using several address variants

It is essential to know exactly who you are sending your email to and what their published email address is. If you’re not sure of the address, it’s tempting to make an educated guess (e.g.,,, or

Most corporate email servers have a catchall, so all the variants will get through. They may be matched to the sender and marked as spam. In some cases, however, the person will receive several copies. Nothing says “spammer” like 10 copies of the same message.

And nothing will get you blacklisted by SpamCop and Barracuda quicker than a corporate spam complaint.

Editor’s note: In Friday’s Weekend Warrior post, we talk about the different ways to find email addresses.

Remember: Email is a Privilege, Not A Right

Email is still the most effective means of communication.

Its abuse by spammers and scammers has led to legislation and a technical “arms race” that makes outreach emailing difficult for the good guys too.

Difficult, but not impossible.

We all have an interest in the continued value of email.

It’s up to us to prove we can use this medium with respect and understanding.

You now have the tools to ensure you stand the best chance of getting your outreach emails to the intended receiver.

If you’ve covered all the bases, your recipient will be delighted to continue the conversation.

I’ve also created a free checklist for Mirasee readers. You can download it here.

Tell us what you think. Have you had to clear any legal hurdles or been accused of sending spam? Let us know in the comments.

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