How to do better email outreach

I think I’m pretty good at email outreach.

I’ve done a bunch of it, for a variety of reasons from link building to strategic partnerships to simply wanting to meet up for caffeinated beverages, and have had pretty good success in general.

One time, I even had an unexpected case study written up about my backlink outreach. Kinda cool!

I also get a ton of email outreach because I’ve held the editorial keys at CXL and because I’m at HubSpot (and you just sorta get lots of sales pitches when you’re at HubSpot and people rely on firmographic data to sell things). Like you, I’ve seen bad outreach examples as well as good ones.

Quick Preface: The Problem of Critiquing Outreach (or Critiquing Anything without Inside Knowledge)

I want to say that I need to tread lightly here, though: nothing bothers me more than critique with no knowledge of internal data or skin in the game. After all, “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena.”

In other words, it’s easy to call someone out for “bad outreach,” but they may be crushing it and it just didn’t resonate with you (for whatever reason – maybe you were just having a bad day).

I’m also trying to balance two extremes: staunch moral principles and politeness with business results. I think it can be done, that you don’t need to choose one or the other. I don’t think you need to be a horrible, annoying spammer to get business results. In fact, I think it’s better in the long run if you’re not.

If you’re in the “but the data says it works” crowd for email outreach, and you use trickery like “RE:” in the headline, or follow up 8 times for a backlink, try this thought experiment…

What if everyone in the world were doing what you are?

If you wouldn’t like how the world was in that scenario, all I’m doing is imploring you to take a small step back and reconsider a more strategic approach. Marketers tend to ruin everything, but we don’t have to operate that way.

Another disclaimer: I’ve probably sent some dumb outreach emails in the past. We’re all human, and hopefully all improving. If I’ve sent you a dumb outreach email, feel free to tell me that, but I’m likely aware and regretful already.

So I’ll try to go light on what I personally find grating and draw more attention to the underlying principles behind how I write outreach messages to both get results and remain capable of sleeping at night. I’ll focus on the man in the arena and mostly avoid my personal distaste (mostly!).

First, what’s in it for me?

First: value.

If you’re not adding value (appealing to self-interest), you’re not going to get a good response or success rate, and you’re likely to burn bridges rather than build long term beneficial relationships.

The rest of the rules in my article rely on this implicit assumption: you’re giving some sort of value.

This is maybe a nebulous concept. What’s value? It could be many different things: friendship and favors, the draw of future reciprocity, cold hard cash, stimulating conversation, an introduction, etc.

That’s for you to figure out. But that’s rule #1 and can’t be forgotten. You can’t just email someone and ask them to do something, without giving any value yourself…

What’s in it for me?

5 Rules for Email Outreach

Here ya go, five rules, all from post-hoc analysis at the underlying values behind my outreach email writing:

It doesn’t matter what purpose you’re doing email outreach for: sales development, link building, product launch, partnerships – I’ve done them all. It usually comes down to the same few principles.

In addition, you can apply these whether or not your email outreach is cold. If your email outreach is not cold (i.e. you know the person), you should definitely follow this. The stakes are higher. You don’t want to be a bad communicator with someone you already have a relationship with.

Cold emails have a lower ‘cost’ because there’s no existing bridge you’re burning with shit communication (though you’re altering future opportunities and you may not even know it).

Also, at the core of all of this is that you’re providing some sort of value with your outreach. It need not be something so explicit as money or respect, it could be something as subtle as friendship or a favor down the line. But no outreach email will work if you’re just a “me-me-me” value leech.

1. Talk Like a Human Talking to a Human

For some reason, when we put pen to paper and send an email we forgot the normal way to talk. This is true even in peer-to-peer or colleague-to-colleague communication, but it’s even more true if you’re emailing a stranger or emailing someone to ask for a favor.

For some reason, in these situations, we get weird.

All of this is weird.

Just read your letter out loud before you send it. Ask yourself, “do I sound like a normal person?”

Or, “If I got this email, would I like to respond to me?”

If the answer is no, crumple it up and try again.

(Most of these tips come down to rational empathy and realizing that if you were on the receiving end you wouldn’t like your own email.)

This echoes the best writing advice of all time (by Paul Graham): write like you talk.

Obviously, in some contexts, you need to be more formal than in others. If you’re asking to grab a coffee, it’s probably not necessary to be super formal:

If you’re emailing an executive with an ask that requires lending their time (e.g. if you want a quote for an article), then be a bit more polite and buttoned up.

In general, “don’t miss the forest for the trees.” When I was working on marketing for Service Hub, we did a lot of SEO, which included link building.

We could have went full aggressive link building mode on this (as many do), but part of our goals involved building relationships with influencers. Spamming content marketers asking for links doesn’t build relationships. It’s just annoying. With this in mind, we kept our messaging relatively benign, yet straightforward.

We also wanted to invoke reciprocity, and not solely ask for a link. Because we were additionally seeking writings for our Service blog, we would lead with an email like this:

Straightforward and normal, right? You may not give the link, but it’s an honest attempt and not too grating.

I used to do that in the early, early days of working at CXL, as well. We build a whole content promotion process, and I genuinely wanted to find guest writers in addition to whatever social shares or links I could build, so I’d send emails like this:

With the Service Hub stuff, if there wasn’t a good opportunity for a backlink ask but the publication was still desirable in terms of relevance and domain authority, we’d work to get a guest post secured on the site.

Obviously, it takes more work to create and place guest posts, but it’s worth it if the publication is aligned and authoritative. We found a way to create additional value with this as well by working with internal HubSpot experts who wanted to get their thoughts out on a given subject. For example, here’s a guest post that Blake Toder wrote for the Usabilla blog:

In these cases, the link is cool, but it’s also great spreading HubSpot thought leadership on customer success related topics. We weren’t myopic or transactional in our focus.

Also, leave the crazy at home. Where one side of awful is represented by robotic tone, the other side is represented by mania or weirdness. Both sides are equally counterproductive to your efforts and you should avoid them.

Don’t be weeeeeird

I’ve heard a version of this called “chatty copy,” and I can’t really stand it. Again, as with any qualitative advice in this article, take it with a grain of salt because I’m just one angry person who’s worked in marketing for a while, but when the copy is patronizing and silly to the point of absurdity, it just reeks of “try hard.”

It’s a pretty straightforward tip, but just read your outreach out loud before you hit send and try to put yourself in the receivers shoes. Bonus points if you can get an objective voice to review your email.

2. Save Time, But Not at the Expense of Quality

Another principle my team has is “automate as much as possible without sacrificing quality.”

Fact 1: emails get ignored. Fact 2: More emails tend to increase the odds of a response.

So, we set up HubSpot Sequences and automated parts of our email outreach follow up.

In actual fact, a large percentage of the links we acquired were from the second or third email from our Sequence. I’ll talk later about the diminishing returns of a ton of follow-up emails, but for now, suffice to say that you should probably send more than one.

The emails would gradually taper off in aggressiveness. Email 1 was a direct ask for a link:

Email 2 tapered off and focused more on getting them to write for us or do a quote for an article.

Email 3 was a “last shot” email and asked if they’d give an expert quote for a new article.

We tried to give as much value as possible in these emails without being spammy or annoying. We also tried to keep in mind that all of this influencer outreach was not only about the short-term benefit of acquiring links, but it also served the purpose to stake out a place in the customer success space and build relationships with important, smart people.

Also, if you can, track your outreach and try to improve it with time.

While doing Service Hub stuff, we tracked everything in HubSpot CRM, including what tier the contact was, creating a Deal pipeline, as well as setting up Workflows to remind us to reach out for link asks a few weeks after reaching out to certain contacts.

We also tracked all guest posts we asked for in Deals, just to make sure that everything was in one place. While this was a separate system than what our content team used to track guest writers, it helped us to get a high level view of all of our influencer communications and progress.

3. Don’t Beat Around the Bush

Don’t obfuscate, don’t cut around the edges, just ask for what you want.

In other words, cut to the chase. Let’s not play games. It doesn’t need to be rude, but make it apparent. I can’t remember how many emails I’ve had to respond to with, “what exactly are you asking for?”

The person shouldn’t have to decipher what you’re asking for. Here’s how I did outreach for a recent Product Hunt launch:

Simple, yeah? Hopefully I didn’t break their “don’t ask for votes” rule, because I used the clever euphemism of “give some love.”

In this case, I knew the person I was emailing pretty well. Still, you can take this approach and apply it to cold outreach as well. Here’s an example of a link ask I really liked recently:

I do the same thing when I do link building outreach. I don’t beat around the bush, I make it abundantly clear what I want:

You don’t want to be the person who asks for a social share or, god forbid, for “feedback” on your article. I know this is touted as a best practice by some SEO experts, but it’s really just lying…You definitely don’t want my feedback, so pretending that you do is dishonest (I take it back if you actually want feedback. It’s a BIG ask of someone you don’t know, but you do you).

I’m not the only one who hates this type of stuff:

On this line: don’t preheat the oven by emailing me before you launch an article and asking permission to send it over. I know this is another tactic that everyone thinks works better, but it always makes me think you’re doing that thing where you’re using psychology to trick me. Foot in the door or whatever.

If you want something, just ask. Lay out what’s in it for me (gimme value!), what you want, and make it easier for me to do it.

That last point leads me to the next rule…

4. Don’t Treat People Like They’re Stupid

This is the section where I rant about pet peeves, so if you just wanna learn what works and don’t care for moral finger wagging, move along.

For some reason or another, subtle persuasion tricks, and timely tactics are what get passed around in the marketing space. Nowhere is this truer than in sales and outreach.

How many templatized emails have you gotten in the last 3 months? How many have you responded to?

You’ve heard the same refrains repeatedly:

  • “{{Name}}, are you the right person?”
  • “Is Thursday at 4pm or Friday at 2pm better for a call for you?”
  • “I wrote X piece of content. Do you mind if I send it over for you to check out when it’s published?”
  • “I’m a huge fan and reader of {{your blog}}!”

These all sound innocuous in a vacuum, but they all carry a really cynical underlying principle that marketers and salespeople sometimes have. That belief that, if only you could ‘trick’ the person into saying yes, your outreach problems will be over.

Though there are hundreds of these taught and repeated lines, and they’ll continue to adapt and evolve, let’s walk through these one-by-one just to understand how offensive these things can be…

“{{Name}}, are you the right person?”

This one is pretty transparently annoying. If I’m not the right person, why are you emailing me? It sounds like you need to do more research, not put the onus on me to do your prospecting.

It’s offensive that you’re essentially creating a negative externalized cost where I’m presumed to do your work for you (and stop whatever I’m doing to reply!)

Again, before I’m called out. I’ve appended an email with “if you’re not the right person, my bad, but if it’s at all interesting, can you intro me?”

I genuinely try to reach the right person and sometimes mess up slightly (“business development manager” vs “partnership marketing manager” is a hard difference to know off the bat). My point here is only to shame the disingenuous bunch of simply email a shitload of people at a given company to get some sort of response and introduction.

“Is Thursday at 4pm or Friday at 2pm better for a call for you?”

The logic behind this one is if you given them a chance to tell you “no,” they will. This, instead, forces the choice to be between two different times, which rests on the assumption that the answer to the first necessary question, “do you want to talk to me,” is yes.

Neither time is good for me, so get outta here w/ that Calendly link.

“I wrote X piece of content. Do you mind if I send it over to you when it’s published so I can get some feedback?”

This is my least favorite one, even though on the surface it actually looks like the least presumptuous.

It’s my pet peeve because I know it’s a tactic, I know it’s copied from thought leaders, and I know it’s disingenuous. It is done, not for my benefit and courtesy, but because you read someone online that the click through rate is better when you first send a “pre-heat” email.

I will almost always ignore these, or respond by saying, “no, I don’t want to see your infographic.”

This is such blatant psychological trickery, because it’s so easy to say “sure, send it over,” and pass on the discomfort of rejection to a later date. But this propels the “foot in the door” technique, where you’re now a part of the conversation and more likely to link back to the person or whatever they want.

“I’m a huge fan and big reader of {{your blog}}!!”

Don’t say this if you’re not.

I’m not saying any of this stuff is ineffective, I’m just saying that if you’re trying to ‘trick’ another person into giving you a backlink it’s not very ethical.

Addendum to Point #4

This section is basically a rant, and I realize that may not be helpful.

You may be saying, “Alex, these techniques work. Why would I stop just because they annoy you?”

I’d agree. In isolation. This is one of those cases where you should ask yourself, “if everyone in the world did this, would the world be a better or worse place?”

I struggle writing these sections, because it sounds like moral finger wagging. But I’m just as interested in effectiveness as anyone. I just truly believe that by focusing on these short terms and casually dishonest tactics, we’re burning up the fields for everyone else (and our future selves). They aren’t sustainable tactics.

At the same time, I realize that sometimes you need to be scrappy and get responses. In that case, feel free to treat this like an airy rant and move on. I’ll still try to give some tactical tips in the rest of the article.

5. Follow Up, But Don’t Be Obnoxious

I’ve been thinking a lot about Nassim Taleb’s “Silver Rule”: do NOT do to others what you don’t want them to do to you.

We can easily sit back and say “it works,” because we’re the doers and not the receivers. It’s the same case with the last tip, really; I’m not arguing that it doesn’t work, I’m arguing that it probably makes the world a worse place by doing it.

So, when you read advice on how many follow ups you need to close a sale, think about it from a pollution perspective as well: what if you were receiving those messages?

Granted, most people probably give up too soon. Emails get lost in an inbox. You need to get attention if you’re doing business.

And it depends on the context. If you’re trying to close a massive enterprise software deal, you know, follow up. But if someone didn’t want to link back to your infographic, you really don’t need to email them seven more times.

Here, I think there are two opposing camps. One said is basically saying you should never send cold emails, let alone follow up on them. The other is saying you should do what it takes to close the sale, and that’s almost always several follow ups, usually 7+.

I couldn’t imagine sitting in either camp, so I actually ask myself several questions to contextualize the outreach campaign:

  • What am I asking for? What’s the effort it takes them to complete the request?
  • Do I know the person at all or have some sort of mutual connections?
  • How important is the ask?
  • How much value am I providing them in the exchange?

And then I make an intelligent decision. Sometimes it’s a single email w/ a follow up, sometimes it’s 4 emails. But it depends on the context.

Bonus Tip: Real Relationships Trump the Transactional

If you’re doing tons of cold email outreach, it’s generally going to be less effective than real relationships. People respond to asks according to three layers:

  • Do they know you?
  • Do they like you?
  • Is your ask in line with their goals?

If you don’t have any of those, you better be offering some tremendous additional value. But if you’re someone that is known, liked, and understands the goals of the other person, you have pretty good odds.

People don’t like to think like this, and I think that’s for a few reasons.

One, it’s mushy advice. “Build relationships,” sounds like one of those platitudes like “be yourself.” However, in this case, it really is the only advice that should matter.

Second, it’s hard and a long term thing.

It’s easier to think in terms of subject line trickery and adding cute GIFS to your emails, because those are easy to implement.

They’re also easy to test and prove out with data. If you send a few hundred w/ this email subject line and a few hundred with another, presuming you have somewhat rigorous experimental design, you can get a clarifying idea on what gets a better response rate and completion rate.

Building relationships has no predictable ROI. It shouldn’t. One of the worst types of people in the world is one that expects business ROI from relationships.

Final Thoughts

Most advice on email outreach is pretty good. I’m not adding too much new here:

  • Add value
  • Don’t be super weird or robotic
  • Don’t be annoying or make the world a worse place

But we usually take away the least effective and most short term parts of email outreach advice – he tactical, the short term, the psychological trickery.

Add value, and don’t be a dick.

Alex Birkett
Alex Birkett is a Growth Marketer and Content Strategist based in Austin, Texas. He's a proud UW-Madison graduate and enjoys craft beer, lifting weights, and sailing.

3 Responses to “How to do better email outreach

  • Gurbir
    2 years ago

    “don’t be a dick”. Nice xD

  • Gurbir
    2 years ago

    Hey Alex,
    Something came to mind. For most link requests, you offer them a guest post opportunity. If you do it at scale, don’t you think there is a chance of it being considered as reciprocal linking/link exchanges?

  • Great post, thanks Alex. Super useful and helpful in my SEO outreach process.