How to Practice E-mail Empathy

On communicating more elegantly and effectively in an age of attention scarcity

Mike Sturm
Nov 27, 2020 · 6 min read
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I received an e-mail the other day from a salesperson. It began with two introductory sentences, then a third which read “I’ll keep this brief.”

What followed was two dense paragraphs rich with detail, names, and data. A third paragraph following them was one sentence with a vague “it’d be great to connect” wedged in there. No call to action, no specific request of how and when we might connect. Just an inkling that it would be “nice” to “connect”.

I don’t plan to respond the e-mail.

Why? I have no idea what the objective is. I lost it somewhere between the author’s initial promise to “keep it brief,” him smashing that promise to pieces in the 2 dense paragraphs following that, and the concluding sentence which seemed like the equivalent of wishful navel-gazing.

If you make it a point to say you’re going to keep it brief in an e-mail, be sure to actually keep it brief. Failing to do so is a reflection that you haven’t taken the recipient of the e-mail into consideration. You haven’t thought about what it’s like to receive a huge, sprawling e-mail with a bunch of dense text in it.

E-mail Empathy

At some point in the past — perhaps 10 or 15 years ago — it may have been helpful to send a detailed and dense e-mail. After all, the more words you include, and more detailed of an outline you send, the more time and thought you put into it, right?


From the sender’s point of view, it may feel great to write those long, dense e-mails that lay out a bunch of information in one place. Usually, writing that e-mail is the first chance the sender has had to really think through all of that information. As a result, once that e-mail is written, the sender is proud of that accomplishment and wants to send it off. But 9 times out of 10, that’s a mistake.

As any writer will tell you, it takes significantly more time and thought to write fewer words than it does to write more. The first draft of an e-mail will be too much — too many words and too dense. It shows your eagerness and nerves, but neither of those things add value to the recipient of the e-mail.

The recipient of your e-mail — just like all of us these days — has precious little time. Their lack of time also means precious little attention — specifically for your e-mail. So be sure the e-mail they receive is as short, direct, and clean as it can be.

Knowing the purpose of your e-mail 70% of the battle. Are you looking to get information from the recipient? Are you trying to set up a meeting with them? Are you looking for a commitment, a document, an introduction to another person? That goal is the first thing to type in the e-mail. Then start filling in all the other stuff to help you ease into your request.

If you’re really struggling to state a simple, short objective for the e-mail — or there’s so many objectives, that you can’t pick one — stop. Don’t send this e-mail now.

Instead, sit and think about the most important objective — the objective which, if the recipient acts on that, will snowball into achieving the other ones. Make your e-mail about that objective. And make it compelling enough that there’s a natural progression to the other objectives.

Again, think of the goal of that e-mail and practice some e-mail empathy. Put yourself in the shoes of the recipient of your e-mail. Ask yourself how much time you will likely want to spend on the e-mail, and whether you’d find it easy to find the actionable content.

The easiest way to do that is to practice the concept of less = more: fewer words, and less dense content.

Word Count and Density: Less is Almost Always More

Keeping an e-mail brief isn’t really about how long it appears, but rather how much work the recipient has to do in order to process it. A relatively short e-mail can actually take quite a bit of time to process. That’s where density comes into play.

Brevity isn’t just about word count. It’s also about information density. You can send an e-mail that only has only one paragraph. But if that paragraph is loaded with a bunch of information that forces the reader to slow down and have to process, analyze, cross-reference, recall, or do anything but leisurely read — the e-mail ceases to be brief — no matter how few words are in it.

So aim to not only limit your word count, but also limit the amount of stuff packed into even a low word count. If you must put a bunch of information in an e-mail, use bullet points or numbered lists.

But when you do use bullet points or numbers, keep the items short. Try not to exceed 10 words per item. Also, don’t — under any circumstances — use an outline form. If you are promising to keep it brief, but your “brief” e-mail has indented sup-points — you’ve broken your promise.

The Follow-up Rule

In most cases, the more urgent you feel a response to your e-mail is, the less likely the recipient will respond in your desired timeframe. Truly, a watched pot never boils. But that’s why there’s the follow-up! Follow-ups can be a great way to get the desired attention — but you need to do them in the right way.

The best follow-up to a long e-mail that didn’t get answered quickly is a phone call. Yes, people still use the phone — especially in the professional world. The reason a phone call can help is because people get to interrupt you when you’re bowling them over with a bunch of information too quickly. They get to ask you questions. There’s conversation, with the ability to confirm whether or not there is both understanding of the information and a shared urgency about it.

But if you must follow up with an e-mail, here’s the rule of thumb: your follow-up e-mail should be about 10% of the length of your original. Whatever you do, do not send another e-mail with multiple pieces of information in it. That obviously didn’t work the first time, so pare it down aggressively this time.

When All Else Fails, Just Use the Golden Rule

The simplest way to get more things done using e-mail is use a kind of golden rule for e-mails: E-mail others in the way that you would like them to e-mail you.

When you sit down to craft an e-mail, think of how you would handle receiving the same kind of e-mail in the recipient’s position. You don’t want a long or dense e-mail with an unclear action item. So don’t write one.

If you have dense thicket of information that you need to make sure the recipient understands, e-mail them to ask for 10 minutes of their time on a video call. Then read out the long, dense e-mail you almost sent them. Be sure that you confirm that they understand and care about the information.

Sure, you may be worried that they won’t respond to a request to hop on a call, so you still want to send the e-mail. That’s fine, just manage your expectations. If they won’t give you 10 minutes of their time to make sure they understand your e-mail, what do you think will come from sending that e-mail? Surely not much.

E-mail is a unique form of communication, but it’s still a form of communication. So it shares one crucial thing with every other one: you’re doing it to engage with someone. The more you think about the person or people you’re trying to engage with — and remember that they’re short on time and attention like you — the better your e-mails will be.

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Mike Sturm

Written by

Author of “The Wabi-Sabi Way” and “Be, Think, Do”. Subscribe to my newsletter “Woolgathering”:

The Startup

Medium's largest active publication, followed by +771K people. Follow to join our community.

Mike Sturm

Written by

Author of “The Wabi-Sabi Way” and “Be, Think, Do”. Subscribe to my newsletter “Woolgathering”:

The Startup

Medium's largest active publication, followed by +771K people. Follow to join our community.

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