How to Write a Tough E-Mail

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I am a proud member of the email generation. Few things fire me up like the opportunity to write a long, involved message to someone (just ask Reese)!

The beauty of email is that, like a phone call, it can arrive at it’s destination instantly but, like writing a letter, it offers the time to craft just the right message. Email has found the perfect balance.

Of course, that doesn’t mean there aren’t those occasional situations we come across that require really tough emails, when projects and relationships are on the line. These can be tough to write.

It’s often at these times, when it counts most, that people just vent their feelings, rush to the send button and squelch one of email’s key advantages.

So, how can we write better e-mails in hard situations?

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Figure Out Exactly What You Want

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One way or another, your email will have some effect on the recipient and the situation you’re in. So, what is the ideal outcome?

This is the absolute most important thing to figure out. What do you really want out of this email and ultimately from the other person?

Be honest with yourself here and break it down. Do you want them simply to listen and understand where you’re coming from, to take a specific action or to work through an issue with you?

It is so easy to just get to writing without actually thinking about what it is that you hope to achieve from your message. But there’s no way, then, for your final email to be on focused and effective – what would it be focused on, what would it be effective for?

Figure out what you want so you’re email has a purpose.

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Be the Recipient

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When you’re talking to someone in person, you can see all their humanity right in front of you. When you’re on the phone, you hear every minute shift in their voice intonation and can pick-up on their emotions.

When you’re writing an email, you’re just staring at a blinking cursor.

It’s difficult but critical to connect mentally with the human you’re interacting with. What do they want? Where does that overlap with what you want?

What would you think if you saw the World the way your recipient did and read the e-mail you’re writing? What would your concerns be? How can you show, proactively, that you understand those issues and the person on the other end of the e-mail?

The power of feeling understood is profound.

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Take Your Time

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When dealing with a tense situation, we all know how easy it can be to turn an email into a vent session. But, now that you know what you want, you have to ask: Does this help get me there?

It’s important to be honest, but not swept away with emotion. The more urgent and important a situation, the more critical it is to relax and write with calmness and perspective.

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Time for a Brain Dump

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To find that perspective, take out a piece of paper or open up a text editor (ideally not your email client) and just write whatever comes out when you start thinking about the situation. Sort out yourself before you try to sort out your interaction with the other person.

Don’t worry about grammar, paragraphs, spelling, etc. This is like writing a morning page. Just get everything out.

Try writing out portions of the email to see how they sound in your head, written out and even out loud. Be loose with your writing – go in and out of writing pieces of the email and your thoughts on them once they’re out.

No rules, no demands. Think of this like playing with playdo.

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Go for a walk

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At this point, you probably have all the raw material roughed out for an extremely well-crafted email. Even so, it’s possible that your brain just hasn’t had quite enough time to process all of it. It needs space and time away to do its thing.

The best thing to do in these circumstances is to go for a walk and let your thoughts wander. You may think about the situation at hand but it’s no big deal, and perhaps best, if you don’t.

No set length, no set time. Just keep walking until you feel satisfied and ready to write.

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Write your E-Mail!

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For me, it’s simply a reflex to open up a new email, type the first few letters of the recipient, hit enter to select them, hit tab, add subject, hit tab and write my email.

For an important email though, I like to break that up and not fill in anything until after I’m done writing the body.

Aside from the danger of accidentally hitting send, I just find writing with no recipient to be much more relaxing. The email feels like less of a commitment and still a work in progress rather than something that might be shipped off any second.

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Now, you know what you want, you’ve given yourself time to fully explore and process the situation and played around with lots of different possibilities for your email. You’ve even filtered all of that through the recipient’s perspective.

All that’s left is to bring that content together, craft it to concisely and effectively achieve your ideal outcome and hit send!