New Pro Rules of Emailing a High Value Person

Make it as easy as possible for them to simply say, "Yes."
New Pro Rules of Emailing a High Value Person
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Entrepreneur Leadership Network Writer
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6 min read
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Yes." It was one of the shortest emails I have ever received, from a billion dollar company.

Years later, having worked with businesses of all sizes, including Fortune 500 and S&P companies, I realize how lucky I was to receive that email.

He had no idea who I was.

The fact that he responded wasn’t an accident, though. I spent years deliberating over what to say in emails, and then waiting, following up, waiting, and following up again for months before finally realizing that it’s a total waste of time and that they’ll probably never respond. The average professional now spends about 28 percent of their work day on emails.

But imagine if you didn’t have to spend nearly that much time or effort and still be able to get in touch with potential clients, mentors, or even influential people you admire.

Well, you don't have to. In fact, it's better that you don't, because the old ways of reaching out to someone for the first time with a long ‘professional’ email are now dead in the water.

Here are five new ways you can get them to stop scrolling past your email and even respond to you, even if they have no idea who you are.

1. Respect their day and reach out before or after hours

Big leaguers don’t always have the opportunity to sit down, relax, and look through what’s on their calendar, much less their full inbox. Their work day is usually filled with meetings.

And yet, many of them rise early and stay late to get ahead.

So how can you break through the noise?

Schedule sending your email when their day is likely to have more breathing room, which is just before and just after business hours. Particularly if they also work from home and have a family, this is prime time for you to get in touch with them.

This doesn’t mean, of course, that you can email them in the middle of the night. But if you send it around 6:30-8:30 AM or 4:30-6:30 PM, there’s a better chance that they'll stop at your emails when there are less distractions.

When in doubt, start with what’s best for them, not for you.

2. Start with their passion, not your profit

Wherever I look, I hear the same advice: Add value. The only problem with this, though, is that it’s easy to assume the value that you want to give, is the value that other people would like to receive.

If you don’t start with them first, particularly what they’re interested in, it can be impossible to shine in a crowded inbox.

Try starting with topics that they said they’re passionate about, but have yet to get much public attention.

As an example, if you want to get in touch with a world-renown leader, and you’ve seen that they often talk excitedly about an upcoming triathlon that they’re competing in, you can open with that, instead of their work, which they would typically expect and may even find dull at times.

Related: This Experiment Reveals the Best Way to Send a Cold Email.

3. Stop them with short subject lines

This goes back to starting with the reader in mind, as it should. Many people now consume emails on their mobile phones.

And when they hold up their phones and look at your subject line, their screen size limits what’s visible to only five to seven words. This means that if you’d like to get their attention, your subject line must communicate your email contents within that word count.

Longer subject lines that require them to click and open to find out more is extra work that most people aren’t usually willing to do.

To focus their eyes even more, begin the subject line with “RE:”, which has long stood for “regarding” in memorandums and office settings. Now though, as more people commonly associate it with “reply”, it can serve as a professional way to grab the reader’s attention.

This means that a subject line can look like, “RE: Thanks for [their topic of interest, e.g. your talk on the Summit247 triathlon]

Related: How to Write Email Subject Lines That Will Actually Be Opened.

4. Be specifically curious, not crafty

Inundating the reader with impressive industry jargons is a good recipe for getting ignored. There is definitely time and place for you to show your worth. But your first email is hardly the time.

It’s like asking to move in on a first date.

Show the reader respect by giving them the opportunity to make their own decisions, including whether or not they’d like to engage with you.

Open with one brief sentence about who you are first so that they know you’re not another email they should ignore. Then, you can dive into reasons why you're emailing them. 

Your first couple of paragraphs can look like this.

I’m [your full name], [your title] who [insert top relevant experience, like “helped PepCon jump to 30% growth in one year”].

I’ve been wanting to get with you on [insert SPECIFIC topic, like “your talk on the Summit247 triathlon”] [insert how that topic had SPECIFICALLY impacted you, like “which helped me get out of a rut and finally act on a business idea I’ve put off for 10 years now”].

Related: 11 Strategies to Change How You Email.

5. A single clear question is better than a slew of requests

I can’t tell you how many times I’ve received emails that have five different requests spread out throughout two to three pages. Responding to something like this eats up both time and energy.

At any given time, though, top CEOs and big leaguers may have just one or two minutes to respond. Their responses can be equally short, too: just one or two lines for both small AND big decisions.

If you don’t want your email to end up in the trash, have just one clear question at the end of your email.

That’s it.

This can be something as small as “Which of these two times, [Day/Date/Time One OR Day/Date/Time Two] might work best for you?” or as thoughtful as “I can be flexible next week. If it’s easier, would you like me to send more on this topic first?

Make it as easy as possible for them to take just minutes to reply back and say “Yes!


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