High stakes email checklist

I’m making a little cheat sheet for myself. As I progress in my career, much of my work revolves around communication, and I’d be remiss if I don’t share a formal framework I use. I like checklists, spreadsheets, and anything else that organizes the world around me, and it’s fun to make one about communications.

Checklist

This is a checklist for high stakes emails, let’s dig in:

• Goals
  • What are you trying to accomplish? Why? (It could be worth asking why multiple times.)
  • Will this email help you accomplish the goal?
  • Can the goal be summarized in a single sentence? If not, it’s probably not specific enough.
• Audience
  • Who is the audience?
  • What does the audience care about? How can you connect the subject of your email to things they care about?
  • Does every recipient need to be there? Who’s missing?
  • What action do you want the reader to take? Is there a clear call for action? For executive communications (who have notoriously short attention span), you’ll want to both start and end with the same call for action.
• Content
  • Is there a nuance that would be lost in email that requires face to face conversation? Does this need to be an email?
  • Does every sentence and paragraph support your goal?
  • Does this need a TL;DR?
  • Is the narrative structure in place? Is there a clear beginning, middle, and end? No need to write a novel, but without this the content risks being disjoined.
• Impulse
  • Is now the best time to send it? Friday afternoon is almost always a no-no, unless you purposely want the reader to pay less attention to the issue.
  • If this was shared broadly, would you rephrase it? If yes - you definitely should.
    • To double down, if email is about someone, write as if that someone will eventually see it. It’s fine to be candid, it’s not fine to be rude.
  • Are you angry? Upset? I get notoriously cranky in the late afternoon, and avoid sending anything important until the next day - or, if time sensitive, until taking a short break or a walk.

Example

Let’s apply this to an example. Say, I’m writing a book, and the editor I’m working with hasn’t been responsive. I’ve tried talking to them about it, but they’re not responsive. I think it’s the time to escalate to their supervisor.

Here’s the quick, dirty, and impulsive draft I would write:

Hello X,

Y hasn’t been responsive when reviewing the chapters, and it’s really difficult to get back to chapters after a whole week passes by. By then I don’t even have the context! I’ve raised this multiple times and to no avail. Can you please get Y to be more responsive or find another editor for me to work with? I haven’t been able to make meaningful progress in a month!

Pretty brusque, isn’t it? I don’t normally dissect every email like this, but sometimes it helps to take a closer look and formalize the decision making behind each sentence. Thankfully, much of this becomes habitual over time.

Goals

First things first, I want the editor to be more responsive. Why? To have a shorter feedback loop when it comes to making changes. Why? To make it easier to write - it’s difficult to come back to the chapter after a long amount of time passed. Why? This pushes back timelines for each chapter.

I don’t really care about how to achieve this goal: the same person can be more responsive, or maybe I get a new point of contact to work with. Maybe there are other options I haven’t considered.

To summarize in a single sentence, the goal is to “reduce the feedback loop”.

Audience

The audience is the editor’s supervisor, or maybe someone else from the editorial team who’ll have the incentive to escalate.

I know that the timelines are very important to this publisher, which is something I can use. I can frame the concerns around impacts of the timeline - even if it’s not something I necessarily care about myself.

Since there are multiple ways to achieve my goal and I don’t particularly care about how, I can make the call for action open ended. I’m doing this because I’m comfortable with either outcomes - like the editor not being to improve response times, but the publisher providing more leniency around the schedule - which, while isn’t ideal, still helps.

Content

As multiple people can help me accomplish a goal, and I might not be aware of all of relevant parties - email format works best.

Narrative structure here is simple - I have a problem (the beginning), here’s why it’s bad (the middle), let’s fix it (the end).

This email is short enough not to require a TL;DR.

Impulse

As my concern is about a particular person, I have to talk about them. I don’t want to avoid candor, but I can approach the situation with empathy and assumption of best intentions something along the lines of: “I understand X has other commitments”. Focusing on facts and leading with empathy would help here.

Having an unresponsive editor is definitely frustrating, so it’s worth taking a step back, and maybe paying extra attention - there’s no use having frustration show through.

The result

After running through the checklist, we end up with (what I hope is) a better, more actionable, and less icky email:

Hello X,

When working with Y, it takes up to a week for me to receive feedback on the chapters I wrote. I understand Y is working with multiple engagements, but I’m concerned about the timelines for the book. If we continue as is, it’s likely we’ll have to push publishing date by X months.

Could you help me find a resolution here?

It’s short, omits unnecessary details, and leaves the reader with a clear (but open ended) call for action. Now, all that’s left is to schedule send that email in a morning, and wait for a response!