Experiments In Outreach Emails: Surprising Ways To Entice

11 February 2019

Posted in: Outreach

How many emails do you get on an average day? I don’t use email to communicate outside of work purposes (and I very rarely use my personal email for professional purposes), yet I still get inundated with fresh fodder for my spam folder and bin. I unsubscribe from mailing lists when I remember to — at least, when I can do so without having to reset my password so I can log in purely so I can tell them to stop sending me emails — but it doesn’t stem the tide.

And with so many emails piling up in my inbox, I barely even see them. I opt for a high-level scan that checks for indicators of importance (names I recognise, attachments, titles that use my name in a way that clearly wasn’t automated) before marking everything lacking clear value as read (or just deleting it right away).

If I had to guess, I’d say that you’re no different, and nor is any of the recipients of your outreach emails. Too many emails, and far too little time to give any of them the benefit of the doubt. The result? A really hard time for anyone doing email outreach work. If you want to get past that filter, you need to do something fresh — here are some tips to help you out:

Get mysterious with the subject line

Ah, the email subject line. It scarcely seems fair that something so limited could have such an impact on everything that follows, but it does. Most people don’t get previews of email content — they need to decide whether to open their emails based purely on their subject lines (and sources) before they can see anything inside them.

This is the first filter of your outreach emails, and the most dangerous. If you get it horribly wrong, then it won’t matter how good your emails are because no one will open them to find out. All your hard work — those lovingly-crafted paragraphs — will go to waste. So what’s the magical secret to the perfect subject line?

Well, those who’ve A/B tested the process in a big way have reached various conclusions about which elements work, how many emojis you should use, and when you should use first names. But I contend that the most vital part of making an email unmissable is being mysterious to just the right extent. Let’s try making a title for pitching a new graphic design service:

Graphic Design Service Proposal. That’s an adequate (though exceedingly dry) name for a formal pitch document, but how does it fare as an email title? Not that well. It’s clear, telling you what you’ll find inside the email, but if you wanted a dry pitch, you’d solicit it. It feels like an odd choice for email.

So let’s try something different: Graphic design? We picture it differently… What would you make of that if it popped up in your inbox? Would you find the lack of clarity enticing? It gives you the subject matter, alludes to a grand mystery of sorts (what does this fresh vision of graphic design look like?), and trails off to leave the reader in suspense. That ellipsis leads somewhere. Don’t you want to find out where?

Think of the subject line as just one door in a hallway filled with them. Run-of-the-mill material won’t draw anyone in, because they can find it anywhere. You need to give the impression that your door leads to something remarkable. And mystery is the way to do that. Of course, you’ll really need to deliver something remarkable if you want it to pay off… but if you don’t believe that you’re offering something impressive, you have much greater problems than emails!

Display a cool confidence

With any luck, you’re already far past the point of starting unsolicited business messages with “To whom it may concern” or avoiding contractions like the plague. All that stuff is completely pointless today (see, I can even get away with saying “stuff” in this business-centric piece) — anyone responsible for handling emails for a business with digital dealings is exceptionally unlikely to object to everyday language.

But this isn’t just about your lexical or punctuational choices: it’s about everything, from how you greet recipients to how you present the advantages of whatever you’re offering. You should come across as relaxed and confident. There’s such a strong chance that your suggestion will be rejected (or not read at all) that there’s no sense in standing on ceremony out of fear.

Now, I’m not saying that you should ramble incoherently or treat whichever person you’re emailing like your best friend. Instead, imagine that you’re the closer — the salesperson brought in to seal the deal when someone is just a nudge away from accepting. Make your case in the fashion of someone imbued with unstoppable confidence.


After all, a funny quirk of human nature makes us readily assume that confidence is warranted. This is why a self-assured buffoon can rise through the professional ranks, while a competent but quiet and introspective worker can be overlooked.

Remember: when you pitch something through outreach, you’re not asking for a kindness. You’re doing them one. As far as you see it, they’re getting the best of the deal, and they’d be outright foolish to pass up that opportunity. Believe in the value of your pitch, and others will believe in it too.

Ask plenty of questions

Why are questions valuable rhetorical devices? Do you really need me to tell you? A question immediately puts the reader on the back foot, because even if they don’t want to answer it or even think of it, their brain will start working on it anyway. It’s a cheat code for life. And questions are particularly useful when you’re expecting resistance to whatever points you’re trying to make, as is the case in an outreach email.

If you convince someone to open your email, they’ll want answers to their questions: what’s in it for them? How do you work? What’s the cost? But you can’t communicate all of that in a concise way without completely ruining the efficacy of your overall argument. You need the time and space to make your case properly — something they might not want to give you.

So asking a question right off the bat will cut off potential objections and get them following the thought pattern you want them to follow. From there, you can steer them in whatever direction you prefer. Your first question will invite a likely answer, which you can immediately address before segueing into further questions.

And questions of course make your persuasive copy feel less insistent. If you’re asking questions, then clearly you’re not pushing that hard, right? Instead of dictating your convictions to them, you come across as being interested in what they have to say (regardless of the truth of that matter). Something so simple can make all the difference.

Adopt an inventive disguise

Doing regular outreach can get awfully dull, can’t it? You’re making the same case over and over again, framing it the same way, citing the same justifications. And the repetition and predictability also damage its potency, because people have seen it all before — but you don’t have to keep using the same approach.

In fact, a broadly-overlooked option is to use a disguise as a creative conceit. I’m not suggesting stealing someone’s identity, though, or even making a concerted effort to convince someone that you’re actually someone else. I’m talking about dressing your outreach up as entertaining fiction that will make people more likely to be interested.


For instance, suppose that you’re trying to pitch a collaborative PR piece to a company you’d like to work with. You could just give them the plain truth (“hey, we’d love to work with you on this project, what do you reckon?”) but they might get that sort of message all the time.

Instead, dress it up with some theatrical flair. Tell them that you’re being held hostage by a crazed professional networking matchmaker, and they won’t let you go until you find a prestigious professional partner for your PR project. Apologise for the inconvenience, but note that it’s not your fault — you didn’t ask to be kidnapped, after all.

Spinning that yarn is completely harmless. It doesn’t conceal your intentions, and it’s clearly not an effort to genuinely deceive anyone (that’s the advantage of going for an unmistakably-absurd scenario). It’s just a bit of fun thrown in to entertain them and possibly convince them that working together on a project would be good for all parties involved.

Pare down the suggested action

Suppose that you’ve done everything we’ve looked at so far: brought people in with an alluring subject line, adopted a confident tone, asked a lot of questions, and livened up the entire thing with an entertaining veneer. The reader is awed by your rhetorical prowess, and everything is going swimmingly up until the point at which you… ask them to fill out a form.

People don’t like filling in forms. It’s arduous and boring. Ask them to do something arduous at the conclusion of your outreach email — really, ask them to do anything that takes even a mild amount of effort — and they’ll feel slighted. Remember how important it is to act as though you’re the one helping them out? The more you ask for, the more that framing shatters.

You might think “Well, I don’t ask for much: only for them to get back to me with a thoughtful reply”, but they probably don’t want to think about what you’re suggesting. They don’t know you, they don’t trust you, and all they’ve had from you is one email (however well composed). To combat this, stop asking them to think. Ask them to take a tiny action to let you know that they’re not completely opposed to your idea.


What works for that? Well, you can get creative. Ask them to reply with a set word or phrase, or even just a symbol, and tell them what they’ll get for it. For instance, you could say “Want to know more? Reply with a question mark (just “?” will do!) and we’ll send you some answers right away.” It doesn’t take long to send that reply, so if they’re at all interested, they’ll do it.

Alternatively, you could put a button inside your email (if it’s more than a plain text email, for instance), though be mindful not to make it too showy. The glossier the aesthetic, the more generic it will feel, and the more readily it will be discarded as a meaningful option. If you make it clear that it’s something they’ll benefit from doing, and you make it incredibly simple, then you’ll get the results you’re looking for.

Examples: bonus section

Now that I’m done talking the walk, I’ll briefly walk the walk with a couple of example emails drawing from the suggestions I’ve made. See what you make of them!

Example Email #1: Dead Link Replacement Offer

Subject line: I love your website, but something’s missing…

Hey there! I’ve been browsing your website (it’s really solid, by the way — I particularly liked [article X]), and I noticed that a link on your homepage to an accounting software comparison is dead. Well, it isn’t just the link — it’s the piece it leads to.

I checked the site and it’s just gone. Any idea what happened? Maybe it was on a self-destruct timer like something out of Mission Impossible. Reached a certain date and kaboom, exploded. I don’t know the answer, but I do have a great idea for fixing things.

Let me write a new piece to replace the old one.

I’ve been meaning to write a piece about accounting tools for a while now, but I keep putting it off because… well, mediocre digital content keeps making me sad. But now that your quality stuff has perked me up again, this is a golden opportunity to get it done, and (if you like it enough to link to it), get some extra site views from your terrific audience.

Here’s what I’m thinking: I get the piece done in the next week or so, then send it to you for review. If you like it, I make it live on my site, and you get a brand new link to plug up in that hole in your site. Everyone wins!

So what do you reckon? If that works for you, just send me a quick reply. Something like “Sure” or “OK” or “LINK ME UP” would be perfect. Cheers, and keep up the good work!

Example Email #2: Product Sponsorship Suggestion

Subject line: Free stuff: yay or nay?

Howdy! You’ve received this email because you’re a hot commodity in your community. A hot commun-odity. The point is, you’ve got some serious influence, right? You say “Jump!” and your followers ask you why you need them to jump, but they’re definitely curious about the whole jumping thing. And we like your followers.

We like them because they’re exactly the types of people we built [Product X] for. We may be biased, but we think it’s the best on the market, and that no one can compete with our level of quality. But what do you think? That’s what we’d really like to know — so we’d love to send you some FREE STUFF.

What’s the catch? Well, we hope that you’ll try what we send you, and — if you like it, at least — let you followers know about what we have to offer. Sure, you could totally take the stuff and call us idiots on a stream, but our boss is pretty obsessed with your opinion… plus he’s said some version of “We have too much stuff, damnit! Give something away!” several times today, so we’re definitely on the clock here.

Even so, we don’t wanna throw you stuff you don’t want, so let us know if you’re interested. Just send us a nice reply, or settle for a simple “#SWAG” or “FREE STUFF YES”. Or be creative with it, as long as it sounds affirmative. Cool? Cool. Peace out!

There you have it: five tactics for sprucing up your outreach emails and alleviating the creative frustration of doing the same things over and over again. You don’t need to do all of them at once, but try working one or two into your next outreach email. You might be surprised by how differently people respond!

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