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How To Win With Email: 4 Rules For Success

By |July 29, 2019

The business world runs on email. In fact, studies have found that the average professional receives 121 emails every day.

Winning with email starts with having the right approach. 

Use these four rules to guide your email efforts, and increase the chances your counterpart responds to each message you send as you hope they will:

  • Rule No. 1: Less is more.
  • Rule No. 2: Set it up. Don’t catch them off-guard. 
  • Rule No. 3: Land it. Take the time to soften the tone.
  • Rule No. 4: Always end with encouragement or a positive note.

But first, watch this video to learn how you can win with email. 


Rule No. 1: Less is more.

You write brilliantly crafted emails only to have the recipient pick out one small point and ignore everything else. The receiver frequently misses your main point or doesn’t answer the question you posed at the end of your message. 

It seems like email’s original purpose was to make life a little bit easier. But, for some reason, much of the time it seems to make things more difficult. 

If you were playing chess via email, would you lay out your next seven moves in the same email? 

Of course not. 

Any email more than five lines long is bordering on being too long.

Land one point in an email.

Just one.

Rule No. 2: Set it up. Don’t catch them off guard.

You’ve seen the email that starts off with all sorts of flowery stuff only to be followed by “Oh, by the way ... ” and then they lower the boom on you.  

This happens so often that it has even earned an unofficial name: “The Oh, by the Way.”

This likely comes from a bad (but common) bit of advice called “The Sandwich Rule.” This rule says that if you’ve got something negative to share, you should “sandwich” it between two positives. 

This approach sort of goes like this: “I love you. You stink. I love you.”

The Sandwich Rule probably came from a confused mind that couldn’t decide whether it was better to make a good first impression or a good last impression—while being too lazy to actually figure out what’s called for in each.

If bad news is coming, don’t encourage your counterpart to drop their guard with flowery nonsense. Instead, be direct and warn them—using a little bit of tactical empathy:

  • “This is going to sound harsh.”
  • “I’ve got bad news.”

Labeling negative emotions defuses them. If negative emotions are imminent based on the news you are about to share, labels can help soften the blow—or even inoculate your audience from it altogether.

Bottom line? Give your readers the opportunity to brace themselves for bad news by letting them know it’s coming. 

Rule No. 3: Land it. Take the time to soften the tone.

Your counterpart will never read the tone of the email the way you’d like them to.

Give your email a friendly and welcoming nature by taking the time to add in specific words and punctuation that support this effort. Lacking these crucial elements means your emails will have a cold tenor at best—and, far too often, they’ll even have a harsh tone that will work against you.

Liberal use of phrases like I’m sorry and I’m afraid will go a long way toward softening the tone of an email with any piece of bad or potentially negative information you have to share.

I’m sorry, but I’m afraid I just don’t see it that way is a thousand times better than I don’t see it that way.

For positive or even neutral emails, exclamation points are great ways to express energy. 

Sentences that end in a period will likely be received as flat and cold—even when the tone you heard in your head was upbeat.

Rule No. 4: Always end with encouragement or a positive note.

One of the Black Swan Group’s Negotiation Laws of Gravity, which was inspired by Oprah, is this: The last impression is the lasting impression.

This applies to email as well. Use this law to your advantage in all your negotiations.

Here’s an easy way to do this: Take the kind words you wanted to start your email with and put them at the end.

Tell a positive yet indisputable truth like:

  • “The reason we’re reaching out is that we’d like to come to a resolution that everyone is happy with.”
  • “We have high regard for you as a company and as a person.”
  • “We have always enjoyed working together.”
  • “We’d love to have a long and beneficial relationship.”

These are just a few examples. But you should get the gist. 

Whatever you do, the end of your email is not the place to get in an assertive last word, express your dismay, or score some other cheap shot.

What you write last will ring in your counterpart’s ears and repeat over and over in their minds. 

The seeds of your next interaction will be planted here. So be sure to plant them in a way that makes it easier to harvest success.

The takeaway from all this? Use these four rules to inform every email you write, and enjoy better business outcomes. 

It might sound too simple to be true. But trust us: It isn’t.

Get more prepared for your next negotiation.