Escaping e-mail hell

This was first published on my mailing list The Looking Glass. Every week, I answer a reader’s question.

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How can I write more effective e-mails in less time?

Q: I spend way too much time writing e-mails. I tend to be very detail oriented, sharing tons of context and thoughts to my team and managers. But as a result, every night I stay up way too late writing long, multi-paragraph e-mails. It’s affecting my sleep and upsetting my wife. What’s worse, my long e-mails aren’t even effective. Sometimes I’ll run into someone days later and they’ll say “I saw your e-mail, but I haven’t had a chance to read it yet.” Can you help me escape e-mail hell?

Love it or hate it, e-mail is likely a major part of your job. Even with modern replacements like Workplace or Quip, asynchronous written communication is essential for sharing plans, providing feedback, and aligning teams.

And as your team grows, you’ll have more people to connect with, and more and more e-mails to write and respond to.

So, how can you stop having inbox-zero FOMO, get your points across succinctly, and save your marriage? Read on.

Make sure you’re actually focused

Before you can attempt to cut down your e-mails, let’s be sure the problem is actually that you’re spending too much time writing, and not that other distractions are holding you back. My recent article about staying motivated addresses this topic. All good there? Let’s continue.

Build the skill of brevity

Simply beating yourself up by saying “I WILL write shorter e-mails next time” isn’t going to work. You can’t just will yourself to change an ingrained habit. Like any skill, communication requires practice. So, acknowledge that this will take time and effort, but this investment in self-improvement will pay off in the future.

Here’s a technique to practice. Take an e-mail you’ve already written in your normal fashion. Now, edit the e-mail down to half the words. This may involve removing some words or sentences, or you may just try re-writing the whole thing from scratch. Pay attention to what’s different between the longer and shorter versions. Which parts were actually essential, and which parts were extra cruft?

I’ve practiced this with a speaking coach before, where she gave me 60 seconds to answer a question (e.g. “What is your team working on and why”). Then, I’d answer it again in only 30 seconds. I was stunned how each time, the 30 second answer was more focused and clear.

Avoid squishy words

Squishy words are your greatest enemy. Self-defeating phrases like “I feel”, “I’m not sure”, “perhaps”, using the passive voice, or pretty much any adverbs waste time for both you and your recipient, and muddle your point. Studies show that this “softer language” is more prevalent with women, so ladies be on the lookout.

Learn to recognize the signs of squish. Here are examples for how to transform your text.

Example #1: Giving recommendations

  • Before: “I’m not sure if I’ve fully considered all the pros and cons of each option, but based on what I currently know, I think option 2 is perhaps a good choice. That said, I’m willing to be convinced otherwise if you have a different perspective on this that you’d like to discuss.”
  • After: “My recommendation is option 2. How does that sound?”

What changed:

  • This is an e-mail, not a stone tablet. It doesn’t matter how much soul-searching you’ve done to arrive at your recommendation. If you favor option 2, own it.
  • If you have a question, include a question mark. Asking a question as a long-winded phrase won’t make it clear that you want a response.
  • Before: 52 words. After: 9 words.

Example #2: Coordinating meetings

  • Before: “I feel like it would be good meet again to discuss this topic further. I’m not sure if we’ll be able to meet up again while you are in town this week, but if we can’t make our schedules line up for us to be able to get together in-person before you head back to Seattle, then doing a video conference next week would be really appreciated.”
  • After: “Can we meet again? I’d prefer this week in-person, or a VC next week when you’re in Seattle.”

What changed:

  • Unless you’re talking to venture capitalists, VC is a well understood acronym in the context of meetings.
  • The recipient knows in-person meetings happen when two people are in the same physical location. You don’t need to spell it out for them.
  • Before: 68 words. After: 18 words.

Example #3: Managing people.

  • Before: “Regarding your observation that Jimmy seems to be a bit disconnected from the rest of the team, I think you might be right, and I really appreciate you pointing this out to me. After looking into this and thinking about for it a bit, I’m getting the impression that Jimmy might not have been receiving a lot of directive management, and instead he has been afforded quite a lot of freedom and flexibility in choosing his own projects and self-managing his own priorities. While this is working OK for both him and the team, Jimmy is still relatively junior, so he probably doesn’t always focus on the highest priority work. Moreover, I think he’s not actually getting a lot of input about whether or not his work could be improved. This probably isn’t an urgent problem, as he’s generally being pretty helpful, but I do think there’s an opportunity for Jimmy to be doing more valuable work that’s more tightly connected with the team. I think it would be helpful for him to receive more frequent direction on the things he should be focusing his time on, and also for him to start getting more feedback and follow-up on a regular basis on what seems to be working well, and what are some of the areas where things might be improved. So, that’s what I’m thinking about trying out with him. I’m going to give this a try in the coming weeks, and I will plan to let you know if this appears to be effective or not in improving Jimmy’s work moving forward in terms of being more well-connected with the rest of the team’s priorities, as well as his work being higher quality overall.”
  • After: “I agree Jimmy needs more direction and feedback. I’ll do this next week.”

What changed:

  • Everything. And yet nothing. The exact same meaning was conveyed, except this time people will actually read it.
  • Before: 289 words. After: 13 words.

Know your end before you start

Rushing straight into typing without a clear idea of what you’re trying to say is risky.

Start with your hands off the keyboard. Think about your intended outcome. What questions do you want to ask? What points do you want to make? Quickly type this outline in plainspoken language. Sentence fragments are fine.

You can then flesh out these points if needed, but don’t wordsmith any more than is necessary. With practice, this outline actually IS your e-mail, and you can hit send in mere minutes without getting stuck down a rabbit-hole of endless revisions.

Call out Action Items and names in bold

If you’re buried in a pile of e-mail, odds are everyone else is as well. Make it easy for recipients to know exactly what you want them to do. If there are multiple people on the thread, and there’s someone in particular you want to reply, put their name in bold with it clearly spelled out what you expect from them, and by when.

The almighty TL;DR

Ideally, the whole e-mail is just the TL;DR (“too long; didn’t read”) section. But if more context will help frame what your e-mail is all about, or what the reader should take away from it or do next, start with your conclusions in a “tl;dr” section at the beginning, either as a single straightforward sentence (in bold) or some brief bullet points.

Forwarding etiquette and the dreaded FYI

As a corollary to the above, never forward along a massive e-mail chain without a TL;DR of why you’re sending this and what you want the recipient to get out of it, such as a quick summary of the parts to focus on, or an action item.

  • Before: “FYI. See below. Thoughts?” (Followed by a 20 message deep email involving a dozen people debating a contentious product decision.
  • After: “FYI. See below. Our design team wants to support B2C and C2C in a combined flow, but the sales team wants to prioritize B2C. Please help recommend how we can resolve this.”

Forwarding a huge thread with nothing more than “Thoughts?” at the start is the e-mail equivalent of a flaming bag of dog poop on your doorstep.

Apologize to your wife and get more sleep

A happy marriage and plenty of rest is worth more than any e-mail, and will certainly help you be more effective at your job. Thanks for your question, and I wish you the best of luck changing your squishy ways as you venture forth towards the pearly gates of inbox-zero heaven.


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