How to Write and Update Email and Why

At some point in your career you'll find yourself in charge of something. It might be a team or a project or a problem, but it will be something that other people care about. As soon as you find yourself in this position the best thing you can do is start writing a recurring update email. By this I mean an email about this thing—a team, a project, a problem—that gets sent at some predictable frequency to people who care. It should let them know what has changed, what challenges have arisen, what you've accomplished and what is coming next.

Nothing you do will have so many rewards with so little work.

Why to Write

Sponsor Your Colleagues

A few years ago someone asked me to look at a buggy system that had been bad enough issues that it was getting attention from the CTO. They paired me with one of the best, and most under-leveled, engineers I've ever worked with. He started methodically working through the problem, making much more progress than I was. People wanted to be kept up to date with the issue, which meant I had a good reason to email the CTO every week. The emails I wrote turned into an ode to the works of this under-leveled engineer. Each week I wrote about the amazing work he had done in solving the issue. It ended up being one of the most fulfilling things I've done in my career.

Build An Audience

If you write a great update email, something funny happens: people read it. And then more people start reading it. They'll actually ask you to add them to it. Soon, you have a way of reaching a wide variety of people and controlling a message. With almost no extra work, you have achieved influence.

A Repeating A Message

If you say something once, you haven't said it at all. Communication requires repetition. The medium of a weekly email is one that allows you to build themes and repeat the same thing over and over in different ways until people get it. You can't do that in a one off message.

People Will Want to Appear In It

Your weekly email should be highlighting all the things you team is doing. They know people are reading it. Their managers are probably reading it. They know its going to go out this week and they'll actually start to understand that their work is visible and therefore meaningful. They'll want to do more and more.

Regular Communication Makes Communicating Changes Easy

If you tell someone you're going to do something within six weeks and then on day forty-one you tell them its not going to be done, you've probably surprised them (in a bad way).

If you tell someone you're gong to do something within six weeks and each week you let them know where you are, they won't care at all when you end up needing eight or nine. They adjusted for that weeks ago.

It Forces You to Be Up to Date

Every week you know you have to write this email. Thea means you have to keep up things. This doesn't mean micro-managing and snooping, but it means building up some habits that let you figure this out from the ambient information.

At times you'll find yourself thinking, I have no idea what Judy is working on. And you'll realize you haven't been following along or paying enough attention. And because you want to sponsor her and provide good information, you'll fix that.

You Can Delegate It

If you are going on vacation you can find a teammate to take over. This gives them an opportunity to shift into a new role, one where they'll have to pay attention to things they may have been ignoring. They also get a chance to put their own spin on things and push their own side of the story. It can be a good opportunity for someone looking for new skills.

Keep People From Meddling

A weekly email removes anxiety from Stakeholders. They won't get nervous that things aren't getting done because they haven't heard anything. They'll know that things are moving along and they'll be reluctant to disrupt that.

How to Write

To write a great update email, there are a few things to keep in mind.

Use a Consistent Subject Line so People Can Filter Them

Something like "[Team Update] 2020-02-01" will do. You can add summary to the subject if you wish, just make sure there is something in the subject that people can build a mail filter rule out of.

Use Basic Typography

Don't go nuts on colors and layout, but definitely rely on basic typographical elements to help scan-ability. Headers, bold, italics, lists, paragraph text. That should be all you need. Build a language by using them consistently. Try to draw attention to people with emphasized text so they can scan.

All The Rules of Writing on the Web Apply

  • Make
  • Almost Everything
  • A List

Keep things as short as possible. Link out for any details. Use lists as much as possible. People don't read long paragraphs.

Use Emoji Sparingly

Emojis are great to draw attention to things. Try to stick to a library of around 3-5 and use them consistently. For instance, if something launches, you always use a :tada:. If something is at risk and you need help, maybe an exclamation point emoji. People will learn that language and it will help them scan for information.

No Gifs

In this context, gifs are the opposite of communication. Your recipients will look at the GIF and nothing else. They'll say to themselves, ugh, this gif is so stupid.

Also there's nothing sadder than someone looking for the perfect gif on a Friday afternoon.

Never Miss

Give yourself some window in which to write your update every week and make sure you always do it. People are bewitched by uninterrupted consistency and they will attribute you with abilities far greater than you actually possess just because you never skip one. If you need to, delegate it out.

Introduce New Topics

When a new project or theme pops up, use a little extra space to introduce it properly without forcing someone to click away. The next week continue to do some exposition on it. Then as people are familiar with it, start to simply refer to it and link to documentation or past emails. This will keep the email short bit give people a way to get background if they need it.

Don't Turn it Into a Form

I know you're already thinking this, and you should just stop: Don't ask people on your team to email you updates or fill out a form with their updates for the week. That misses the point: you're not really paying attention to things if you need that and you're taking valuable time away from people. Instead, make sure you're staying on top of things. That might mean reading Slack, running git log, making notes in meetings and 1-on-1's, checking your issue tracker or (sparingly) asking someone for an update directly. It sounds hard, but with a little practice you'll be able to figure out how to do this without bothering anyone.

There is a correlary to this: let your teammates know they can always push things to you if they think you'll miss them. You'll never know everything that's going on and people can feel forgotten if you miss something they thought was important.

2019-10-26