Here are 8 simple rules to virtually guarantee your shot at connecting, pitching or making a sale.
Email is absurdly powerful. Used by everyone, owned by no one and essentially free, it’s flattened social hierarchies making virtually anyone accessible. But with ease of access comes a downside: volume. Email is so easy, we send a lot of it. And while we drown in it, it remains the single most powerful enabling tool to get things done.
- Every startup pitch for fundraising begins with an email.
- Every prospecting or sales opportunity begins with an email.
- Every networking relationship or partnership opportunity is born out of email.
Crafting emails that get a response has become an art. And the art of the open hinges on new rules — grounded in science, cultural awareness and the predictably quirky human nature — to make your message stand out.
Because simultaneous to the message you send, your target recipient is receiving email solicitations backed by millions of dollars in marketing and underpinned by statistical models optimizing for keywords.
Daunting? It gets worse.
By 2019, there will be 246 billion emails exchanged daily.
Your chance to make an impression or get a response, exists in a millisecond window of consideration.
In the last ten years, I’ve worked closely with CEOs and CFOs in banking, technology and consulting. I ghostwrite for a growing number of venture capitalists and startup founders. I make a decent living landing consulting gigs by cold-email and watch the communication behavior of the world’s busiest leaders.
And while influential executives delete hundreds of messages a day, some get read. Some even get a response. The trick is figuring out why.
Here are 8 key factors, based on over a decade seeing and sending tens of thousands of emails, to make your email stand out.
1. Write Less.
Word-count is overrated.
If the supreme law of America can be written in 5,000 words, you can get your point across in 100. As Jay Conrad Levinson says in Guerrilla Marketing, “you aren’t writing for a grade”. University courses have conditioned writing behavior that sabotages professional communication.
Writing like you’re in undergraduate English virtually ensures your message gets ignored. Unlearn the academic perspective, fast.
2. Be Informal
This is the most counter-intuitive point on email approach. It’s also the hardest to implement, but presents the greatest ROI.
Being the asker in an exchange moves us to a place of inferiority. We feel vulnerable. Especially when an ask is associated with things that matter, like funding, a job or product sale.
So we press to establish credibility.
Inevitably, this takes the form of dressed up language that shifts dialogue from natural, normal and conversational to awkward.
Reducing informality is about acknowledging the science behind swift decision making and the role casualness plays in human choice.
The idea is referred to as somatic marker hypothesis.
It sounds complex, but it’s basically this:
Decisions in the face of uncertainty are made on a neurobiological level. Emotions are a fundamental aid in decision making and when unsure about how to respond, feelings subconsciously drive a choice.
Over time our minds have connected cues with emotions. Your job in a cold email is to connect with cues that produce positive emotion and association.
What does that best?
I disagree with the classic email recommendation of formality when you don’t know your recipient.
Does this image below look familiar?
Whether hunting for funding, applying for a job or trying to connect for coffee senders tend to email off some formal derivative of this.
Formality breeds reservation. Reinforcing the idea that we are strangers further dissuades me that this message is beneficial or relevant to me.
And, let’s be honest, a click or response is associated with intrigue about the benefit the recipient going to derive.
What’s your immediate response to the image above: excitement or skepticism?
Have you ever used “inquire” in conversation?
One of the most successful sales people I know intentionally misspells words and uses only lowercase letters in his subject lines.
Master pitchman and fundraiser Oren Klaff swears by the one-word email.
- Powerful people are moving very fast and don’t worry for ½ a second about dotting all their “i’s”, capitalization or sentence structure. They are too busy and have assistants do that for them. Or they’re firing off emails in their Uber.
- Only a friend would be that disregarding of style
- Casualness infers you’re not needy. You’re important and worth associating with.
Is this principle hard to embrace? Yes.
Dangerous and borderline arrogant? Can be.
But does it cue an emotion that improves the odds of an open?
3. Get to the point (and make it obvious).
We overestimate the amount of information needed to make a decision. Additional data is seductive and neurologically, information is addicting. [Learning is associated with the release of dopamine, similar to cocaine].
But it’s also paralyzing your reader.
When you compromise decision making simplicity, readers move on. Layering on information is motivated by fear.
You worry about your ask failing so you pile on context to counteract the worst-case scenarios growing real-time in your mind.
If your case needs to be made via email, and thus requires a bit of text, formatting is your friend. You’ll be hard pressed to find a CEO that doesn’t WhatsApp emojis to their kids. It’s normal.
Don’t be afraid of using bold, underline or a bit of formatting flair to. The whitespace, line breaks and variety in display makes ingestion and consideration quite easy.
This is an entirely appropriate email:
With a brief scan the VC knows:
- That this is relevant based on something they’ve said/presented
- There a brief summary of the company that doesn’t have to be dug out
- Attractive metric performance exists
- There’s an organized set of attachments and next steps, if interested
Make the recipient’s path to understanding and answering as frictionless as possible.
4. Proofread, please.
Casual doesn’t mean sloppy.
Read your email out loud before you send it. And consider the power of the comma.
There is a HUGE difference between:
Let’s go eat, Grandpa.
Let’s go eat Grandpa.
5. Stop Rambling.
As James Hamblin, Senior Editor of The Atlantic writes, brevity signals respect.
Until you can articulate the ‘why’ of your message and its specific call to action or response, you don’t get to hit send. While not only being disrespectful, rambling is the byproduct of trying to sound polished, articulate and worthy of a response. But digitally, it reads as insecurity and disorganization.
On my desk is this screenshot of an email I sent as an undergraduate student in Finance. It serves as a painful reminder about what NOT TO DO in email.
In my prospecting note, I ramble. I careen in and out the passive and active voice. I’m liberal with the adjectives, use unnatural language and focus on myself instead of value delivery for the firm.
Your ask should center on how you will make the recipient’s life better: saving them time, making them money or, ideally, both.
Plus, reader’s attention rates drop off startlingly quick. Nielsen’s research on paragraph positioning from a website eyetracking study is telling:
“…your paragraphs’ sequential positioning relative to your first text matters…the further from the top, the less likely it gets read…”
I don’t get to my ask until the 3rd paragraph. Immediately, content quality aside, I reduce my chance of getting my resume read by 25%.
6. Don’t be sorry.
Nothing kills more email than weak language. Nowhere is this more pronounced than in using the word Just.
Anything following this word get disproportionately deleted. It is the digital equivalent of the feeble office door knock and “I know you’re really busy, but…”
If YOU don’t believe that what you’re pitching or selling matters, why will someone else? Your hesitancy permissions their deprioritizing.
- Just wanted to see if you had a chance to review the…
- Just wanted to see you can meet for coffee…
You don’t need to prove anything. Be simple, be gracious, be bold.
7. Know Your Ask.
Too many emails feature vagaries requiring thoughtfulness on what the ask actually is. Again, you’re dealing with near-instantaneous emotional responses. A buried ask opens your reader to confusion and skepticism. Not the lens you want your message viewed through.
The team as Sales Folk has made a business out of optimizing the cold email. This note, pulled from their company blog, wins in all the wrong ways. The ambiguous and mildly cryptic ask (in green), gives way to three hyperlinks and a prompt to ‘Reply’.
The only thing worse than an ambiguous ask is an ambiguous ask paired with four other unassociated ones. Apple CEO Tim Cook gets 700-800 emails per day. Even if the average business leader gets just 20% of those, you’re looking at 150 emails per day.
There is no way this note gets a reply, clicks on two YouTube links and a download of article on a new lead-gen offering. Your job is to shape the path. Lead readers, without resistance, to one clear, easy call to action.
8. Time it right.
You know that famous book, “Don’t Check email In The Morning”? (It supposedly saps your creative energy for important work).
Well…nobody does that.
Not only do we check email in the morning, we do it at meals, stoplights and in life’s most intimate moments.
Although there is no universally accepted or conclusive argument on open rate timing, visualizing the persona on the other end of that address gives you an edge.
- When do they arrive in the office?
- What are their mornings like?
- Do they travel and thus likely get to email on their mobile device?
- If so, is your ask readily visible on a 3 inch screen?
You get the idea.
For my most important messages, I prefer Sunday or early in the morning.
Lots of people check email on the weekends, but fewer people send them. Smartphones have made this a near certainty. If not, your note is still in line for an early Monday morning read.
Alternatively, opt for a 6:00am send.
If you’re not an early riser take advantage of technology. There’s a delay delivery feature in Outlook and for Gmail users, the Boomerang app to schedule email sends and follow up reminders is second-to-none. In the morning, people are fresh and eager. They’re enjoying coffee and the mood is right.
Despite all the advances in productivity philosophies most of us still open Outlook, start at the top and work our way down.
By the afternoon, emails have stacked up, projects are underway, meetings are happening and the mood has dampened. Don’t send then.
Next time you sit down to craft your message, remember: just because email is simple, does not mean it is easy. But by utilizing best-practice principles around timing, formatting, psychology and prose, you can wield this powerful tool with incredible success.
Charlie Waldburger is an executive ghostwriter and communications partner with VCs, founders and technology enabled businesses. He has crafted blogs, pitches, white papers, case studies and research on behalf of Fortune 500 and startup leaders in Africa, Europe and the United States. His work is backed by more than a decade in corporate finance, management consulting and software. He started his career at JPMorgan-Chase and has worked with notable companies including Microsoft and Tableau Software. Meet him at www.charliew.co.