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.
This is a checklist for high stakes emails, let’s dig in:
- 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.
- 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.
- 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.
- 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
- 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.
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:
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.
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”.
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.
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.
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.
After running through the checklist, we end up with (what I hope is) a better, more actionable, and less icky email:
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!