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

  • Martin EdwardsMartin Edwards

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.

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

Timothy W. Bethune

Love it great info. great update

Martin Edwards

Thanks Timothy, I am very pleased that you found it useful.

Joanna kendall

I could not download the 10 Rules of Visionary Business

Selene Benjamin

Hi Joanna,

It should be working now.


Thanks Martin, this is really helpful. I’m a total noob to email marketing and I appreciate plain English guidance!

Martin Edwards

Hi Lynn, its very kind of you to say so. Its very easy to get carried away wth all the technicalities but at the end of the day the most important thing is to try to be sure that the recipient is likely to value your message.

Quinn Eurich

Hi Martin,

Great post! Appreciate the straight-forward information including the piece that I would not have thought of: Use a valid postal address, company registration, and phone numbers in the footer of the email.


Martin Edwards

Thanks for your encouraging words Quinn. Yes, the address thing, apart from being a legal requirement in a lot of jurisdictions, it also demonstrates openness. If you are building a relationship, that is very important.


Okay. My panic attack has subsided. This article hits the panic button too often and too hard. I checked out a bunch of other articles at other places and they were much more informative. I thought outreach emails were advertisements, that’s wrong. Outreach emails are about contacting blogs, influencers, and such about events in your business. Let’s put all of the legal stuff aside and talk about why I would send an outreach email and what goes in one. had a nice article on this and though long-winded, a great resource.

Martin Edwards

Hi Pat, sorry if I made it too panicky. There are many great articles about how to write the emails themselves and what to put in them. I was hoping to fill a gap which is not so often discussed. The anti-spam legislation of many countries is very clear. Any unsolicited email is illegal. The US is fairly relaxed, but Canada, UK, Europe and Australia have stated that these rules will be enforced. It is my view that so long as you comply with the requirements for “implied” consent you are not likely to get a complaint.


I’m a beginner and this information is greatly appreciated. It’s always good to learn the do’s and don’ts.

Martin Edwards

Thanks Debby, I am very glad that you found it helpful. There is a lot to learn when you are getting started, but actually the principles are fairly simple and you’ll find loads of useful articles here to help with whatever you have planned for the future.

Jamie Wyatt

Thanks for the article. It had not occurred to me that I’d even need to consider international e-mail laws!

Martin Edwards

Hi Jamie, I know it is something most of us would rather not think about. 🙂 When I was writing the article I studied the regulations for all of the more restrictive jurisdictions and going into detail on each would have meant writing a book! But at the heart of it is the desire to stop the careless wastage of people’s time. Of course I was trying to convey the flip side of this too. If you reach out to someone they should feel that you have made an effort to work out what they, as an individual, may find interesting and that by being open about who you are, you will not abuse their trust.

Stella James

Thank you for sharing your knowledge.

Martin Edwards

You are very welcome Stella! Helping each other is what it is all about.

Barbara Legall

So very informative. Thank you Martin for sharing.

Martin Edwards

Very kind of you to say so Barbara, I am glad you have found it helpful – makes it all worth while!

Anthony Metivier

Great info!

What about replying to an email you’ve received from them, specifically as a subscriber to their list? That would seem legitimate enough, but I’m curious about your take on it.

Martin Edwards

Hi Anthony, that’s a good point. In my view, if you are replying to the address that is sending you emails then that would constitute implied consent. I wouldn’t put them on an email auto-responder on that basis though! 🙂 You still have to make sure that what you are sending is relevant and shows a reasonable expectation that they would be interested. Also, finding a personal direct email address and sending to that instead would in my view be breaking the rules. I’m pretty sure implied consent isn’t transferable! 🙂

Ashley Lauren Trexler

Great post! I’ve been wondering about a lot of this. I love the approach of dealing with the toughest laws as your guideline. Definitely sends me in the right direction. Thank you!!

Martin Edwards

Thanks Ashley, I’m very pleased that you found it useful. At the end of the day, we are trying to build businesses built on trust and I have always felt that doing things just because you can get away with it, doesn’t really help that trust building in the long run.

Blaine Wilkerson

I never think about Spam laws in other countries. Although, I must admit: I rarely think about spam at all. Neither online, nor off. 🙂

Your points are very helpful indeed. It’s annoying that we have to deal with spam.

But I wonder if it actually works? And in what capacity?

i.e. Do businesses profit from it (is profit greater than fines)? Or is it mostly attached to nefarious activities (hacking, scams, boredom)?

I’m interested to hear your discovery and/or thoughts on spammer motives.

Great post and Thanks in Advance!

Martin Edwards

Hi Blaine, those are interesting questions and could probably warrant a whole new post! I suppose the quick answer is that spam works for those with no scruples and no desire to build a trustworthy reputation. There would appear to be enough people around who will be fooled by an offer that seems too good to be true that lands in their inbox to make it worthwhile for the criminals to keep doing it. Unfortunately this activity can reflect badly on anyone who wants to use email as a communication medium. Legitimate businesses will abide by the rules and seek permission via an opt-in. A lot of non-scam email is more just a matter of laziness. Its too easy to send thousands of messages out to a list you have bought or rented and relevance doesn’t matter. That’s why the laws were created to try to control it. I think if you want people to respect you as a business owner, entrepreneur, blogger etc. you need to make sure that you are considering the relevance and acceptability of any message you send.

Martin Edwards

My pleasure Mark! I am glad it’s given you some ideas.

Helen McCarthy

Hi Martin,

You clearly know your stuff. Thanks for reminding me that making it into a person’s inbox is a privilege, not a right.


Martin Edwards

Thanks Helen, glad you found it useful.


Thanks Martin, glad I read this-I was about to break the rule…”Call it ignorance”- now I know.

Martin Edwards

I’m very glad it helped you, Ann, I am sure you won’t have been contemplating anything too heinous! 🙂


Hi Martin!

Thank you for sharing your experience. I never thought I could be a registered spammer. Scary!

I try to be super-careful and always use a personal signature. Thank you for all the reminders, Ilka

Martin Edwards

Hi Ilka, it’s not so much scary as irritating. You suddenly find no one is answering, and its difficult to know whether it’s because they didn’t get it or whether they were not interested. At least if you know you are on a list you can do something about it.

Comments are closed.