Emailcraft the Pilot Way

So to start — this isn’t a formula. Or, the blog post might seem like a formula, or a checklist or something like that, but really what it’s meant to be is a distillation of a lot of things that I don’t actively think about when I write emails, turned into something explainable. So maybe it’ll seem like a checklist. Who knows.

Basically: I thought I would sit down and parse out what background processes happen habitually/instinctively when I write a professional email (or any message generally). It’s not meant to be prescriptive, but if the tips are helpful, awesome.

Also, to be clear, none of the scenarios or people I mention here are real.

Safety First

Before you even get started writing, safety first.

What does “safety first” mean here? If I’m writing an email, it means that I draft the whole thing and add the subject line before I put in the email address I’m sending it to. Theoretically I should add attachments before that, but usually attachments are the very last thing I remember to do. If I’m responding in our ticketing system, I toggle the word processing box from external reply to internal note. (This turns the whole box background pale yellow. I don’t draft anything if the box isn’t yellow).

The reason for this is, I don’t want to send it prematurely. If there’s no email address, it can’t be sent; if it’s an internal note and I do record it early, worst case scenario I copy/paste it back in and keep drafting.

(Okay, I don’t do this for low-stakes emails or tickets. But for high stakes ones, you bet. Or I draft it in a word processor. I don’t like sending unfinished emails.)

Drafting & Revisions

Write the whole thing first. Don’t worry about phrasing, don’t worry about terminology, just hit every point that you need to hit.

If you don’t have the word you want or the numbers you need or something like that, don’t go looking it up right now, put it in brackets (eg, “Please make sure you’ve filled out your skydiving waiver by [WHENEVER IT’S DUE]”). and come back. I recommend [square] or <pointy> brackets, they’re easier to CTRL+F search for and find fast.

If you’re saying something vague or nonspecific and you want to be more precise, or if you don’t like the way you phrased something but don’t know why, bold it and come back later. Or mark it in brackets. Just do something so it’ll be easy to find when it comes time for revisions.

Speaking of which, revisions!

Once you’ve hit all the important points you need to hit, go back and grab the terminology and numbers you were missing before. The reason we do this now instead of during the first draft is to keep the flow of the writing while drafting and not get sidetracked.

After that, let’s move on to phrasing. Are you being nonspecific? Is something just kinda off? What’s going on?

If you’re being nonspecific, take a quick check why. For me it usually comes down to a couple of things: a) I’m leaving out relevant details because they seem obvious, like something the person would already know; b) I’m leaving out details because I don’t know them and I don’t want to get it wrong; c) I have to deliver bad news, and I don’t wanna.

None of these are good reasons to be vague. (There are good reasons to be vague. We’ll get to them in a minute.)

  • The details seem obvious, and I don’t want to be redundant. Put ’em in anyway. If the person you’re talking to already knows, they’ll skim it. If they don’t know, then the details weren’t obvious and now they’ve learned something. Even if they refuse to learn anything, you did your best.
  • I don’t know the details, and I don’t want to get things wrong and look stupid. Do the same thing you did for the terminology and the numbers: look it up or go ask.
  • I don’t like delivering bad news. Understandable! But sometimes you have to. We’ll come back to strategies for this in the “Mentality Check” section.

If your phrasing just feels off, nothing related to the details, then you just have to parse out why. For me, I often get antsy when I write something that’s sort of kind of broadly true but not actually 100% universally correct (like, “Everyone loves chocolate cake, so we should get that flavor.” Maybe they do or maybe they don’t, but I don’t know that). Once you know why you don’t like something, you can rephrase it to smooth over the rough patches. (“You all know how popular chocolate cake is. That’s probably a good choice for the party.”)

Sometimes It’s Okay To Be Vague

None of the things I’m saying are universal rules. Can’t reiterate that enough. In any case: sometimes it’s okay to be vague.

Sometimes the phrasing of something feels clunky, but it’s accurate and clear and you don’t have time to fix it. If it’s doing its job, then sometimes that’s good enough.

Alternatively, maybe you don’t have news yet (or aren’t sure of the details), but the message is urgent or it’s been waiting for a long time. If that’s the case, sending a quick “Hey we haven’t forgotten about this and we’re still working on it” message is better than saying nothing, even if you don’t have anything specific to report. You can always come back with the details once you have them.

In general, I recommend going for more detail when you can, but that’s not always an option. Sometimes you can’t wait for the time it’ll take to get answers — you want to get a message out today. Or maybe going deep into the technical weeds is going to confuse the person you’re talking to. Or maybe you want to keep some things private for now, even if they’re relevant.

That’s all fine. In cases like that, the detail you want to provide and need to provide is a matter of judgement.

Take tech stuff. If you can give an informative but general overview of the relevant facts (“We’ll be planting flowers on the moon starting Monday at 10am, which will require us to set up a really long hose.”) you don’t need to go into details that don’t pertain to the person you’re talking to (“We’ll be planting the gardenias in the Ocean of Storms on the moon Monday at 10, which will require a 23 thousand kilometer long hose that we’ll be connecting to a pump in Lake Superior.”). If the person you’re talking to isn’t doing any planting and doesn’t have to set up the hose, it may be worth it to skip those details.

Or you need to get that message out, but you don’t have news yet. “I know Kimberly has been working on arranging transport to the moon, so I’ll be checking in with her today to see if there are any updates to pass along.”

Or even something that’s not really their business, like, “We borrowed the hose and the pump from your least favorite neighbor.” It doesn’t matter where you got the hose, what matters is that you got it. Bringing up the neighbor they hate is just going to cast a shadow over the important part: you have the hose, and now you can get to work watering those moon gardenias.

Mentality Check

This section is going to be a long one. We’ll tackle the scariest one first.

“I Don’t Want to Deliver Bad News!”

I told you we’d get back here! Here we are.

Delivering bad news is the worst. It’s gonna make the other person unhappy, which both feels bad and can be intimidating if you think they’re going to react poorly. It stinks. But sometimes, you just have to do it.

So, for starters: does this cloud have a silver lining? People want to get something, especially if they’re losing something else. So instead of thinking about why the news is bad, think about why the news is happening.

Let’s try this. You’re a birthday party clown, and you have to tell your clients, “I’m not going to be making balloon animals anymore.” Why aren’t you?

  • Because it takes a lot of rubber to make all those balloons, which is bad for the environment. True, and sympathetic, but maybe we can provide something a little stronger.
  • Because I’ve developed an allergy to balloon rubber. No way. Even if it’s true and will garner sympathy. No one is entitled to your medical history.
  • Because I don’t want to anymore! I want to do other things, like learn to juggle. Bingo! This might sound like the worst reason, but it can actually be the best.

So, here we go:

“I’m not going to be making balloon animals anymore. Doing this will use less rubber and lower each birthday party’s carbon footprint, but even beyond that, this change will give me the opportunity to develop my juggling skills, something many people have asked for. I’m excited to be able to offer a juggling act at parties from now on.”

By focusing on the positives that come from this change, you’ve reframed a thing people won’t like (they don’t get balloon animals anymore) as a thing that benefits them (they get a juggler instead) and add a nice little bonus that will make them feel good (their birthday parties will have lower environmental impact).

That said, sometimes news is just bad, and there isn’t a great way to spin it. Either someone might get scared, or someone might get mad. You don’t always know they will, but depending on the type of news, you can prep your tone according to what you expect the worst case scenario will be.

If the news is scary: Sympathize! Let them know that you understand why they’re worried, and let them know potential ways that you or they can address the problem (without caving).

“I definitely understand how stressful a lack of balloon animals can be. However, I do offer juggling with balls, pins and swords depending on what would work best for your party. As another alternative, I’ve worked with another clown who’s very talented with balloon animals, so if balloon animals are vital to your party, you can reach out to them and see whether they’re available to perform.”

(And then provide your friend’s professional contact information, of course.)

If they just won’t like it: Sometimes you just gotta say, “Tough.” Not in so many words, but really — sometimes someone’s going to get mad, and the best thing you can do there is to acknowledge that they’re frustrated and then patiently reiterate your boundaries.

“I understand your frustration, but owing to the reasons I mentioned, I can’t continue making balloon animals at this time. However, I may be able to offer some alternatives.”

(And then give some options — probably the same ones you’d give in the previous example, honestly.)

In general, people just want to feel heard and taken care of. So acknowledge how they’re feeling, and then let them know they aren’t totally screwed.

Of course, sometimes people don’t listen. If you’ve made your case and offered options, and they still won’t meet you in the middle, you tried your best. At that point, there’s nothing wrong with a polite, firm, “No.”

“I Need You to Take Care of This, Please.”

Sometimes people ignore you. It’s really annoying, and you need them to do something, or to answer your questions, and it happens. You can be polite and firm in your reminders; I recommend also being detailed, unless you’ve given those details very recently, because people forget things easily. So here’s an example:

“Hi Cheryl,

Hope you enjoyed your weekend. I wanted to follow up here given that the deadline to rent a pony is coming up in about two weeks, on April 19th. Do you have a timeline for selecting your pony? Alternatively, do you need anything from me, like color or breed recommendations?

Remember that the pony rental agency doesn’t accept checks, so you’ll need to pay by either cash or credit card. If you have any questions for me, please don’t hesitate to ask. Have a great day!”

Let’s break that down.

  • I started with a greeting/well-wishes, to be polite before getting down to business.
  • Then I said specifically what I was trying to accomplish with the email: get more information about the pony rental. Conveying the goal up-front means Cheryl doesn’t have to read very far to find it, so I’m not making her do extra work to figure out what’s up.
  • I reminded her of the timeframe, both general (two weeks) and specific (April 19th). Doing this lets her know that she needs to get moving, because that deadline isn’t to pick a pony, it’s to finalize the rental, and we can’t finalize the rental without picking the pony.
  • I let her know specifically what she needs to do (pick out a pony).
  • I offered to help. This is a nice thing to do because it makes Cheryl feel supported, even though in the end the next thing that needs to get done is 100% her responsibility. In this example I offered specifics about what I can do if she needs it, but you don’t have to (especially if you know the answer to “Is there anything you need from me?” is “No.”)
  • I reminded her of something very important, which is that she can’t pay for the pony rental with a check. This is doubly important given that the pony needs to be rented by two weeks from now, so Cheryl must not accidentally waste time by mailing a check.
  • I reiterated that I’m happy to help (even though again, in this situation, she is the one who needs to get this done).
  • I signed off with another pleasantry, just to be polite. Both “Hope you enjoyed your weekend” and “Have a great day” can honestly be optional depending on how many times they’ve ignored you and how patient you’re feeling, but they don’t hurt.

“Dude, Answer My Emails!”

Sometimes people continue to ignore you after you’ve sent multiple polite reminders, and it’s really, really annoying. This is important, dammit!

So let’s bring in the big guns.

If you’re losing patience & they will be able to see CC’d parties, copy in someone in your company or your department who they know has authority (or who they think has authority). Our ticketing system doesn’t let people know who’s CC’d, so in that case you may want to mention, “I’m CC’ing in my boss Sotirios, who may be able to help you with any higher level questions you have.” Note that your boss doesn’t need to actually participate as long as the person you’re talking to knows they’re on the thread, but if they still don’t respond and it’s really important, then your boss can step in smoothly.

If you’re really REALLY losing patience and their boss, or a person in their department with more direct power to do what you want, isn’t on the thread, it may be appropriate to CC that person in. This is not a first resort. Bringing in their boss means both pulling someone new into an email thread they probably don’t want to deal with, and showing the boss that the person you’ve been talking to hasn’t been fulfilling their responsibilities.

If you do this, do not use that email to be rude or pushy, or to point out all the things the other person has done wrong. Be polite, be firm, reiterate everything people need to know, but don’t call people out. You’ve already escalated the conversation, and at this point being a jerk will reflect poorly on you.

In general, I send an email that follows similar principles to the last one I sent, though maybe a little shorter — the email history will have the details included.

“Hi Cheryl,

Just following up on that pony rental. Since the rental deadline is coming up on the 19th, I wanted to check in and see whether you had a timeline on when the pony will be picked, or whether there was anything you needed from me to make that happen. Let me know if so — I’m happy to help.”

Sanity Check – Let’s Pull In a Cooler Head

Sometimes people are jerks, or they’ve ignored you for the fourteenth time, or they’re making you feel like an idiot and that pisses you off. It’s fine to write emails while angry, but don’t send them like that.

If you know you’re angry while writing the email, get a sanity check from a second party before sending it. You can’t always do your own check if you’re in that headspace. Just let someone know, “Hey I’m getting really frustrated & want to make sure this email doesn’t convey that (to an inappropriate degree)” & ask them to take a look.

Note: When I say “to an inappropriate degree,” I mean that it’s fine to convey (not outright state) “The way you’re speaking to me is unacceptable, and you need to stop.” There are politer ways to phrase it, which is why you should ask for a second opinion, but if you write something angry and then try and soften your tone, it’s possible to soften it too much and risk surrendering your boundaries. It’s important to be polite, but it’s also important to stand up for yourself.

Pushover Check – Don’t Apologize So Much!

And on that note: you don’t necessarily have to apologize! Maybe you want to soften some bad news, or compensate for being angry, or you’re otherwise worried about how your message might be received. If that’s the case, you may be pretty apologetic while drafting. THIS IS NOT ALWAYS NECESSARY, and it can even feel crummy while you’re writing.

Look for places where you are being apologetic or deferential, & decide whether they’re necessary. Even if the situation does warrant an apology, you can keep it to one, maybe two if things are really drastic. But you don’t have to grovel throughout the email. You are allowed to be confident in what you’re saying.

And hey, sometimes there are people that you just can’t win with. And that’s fine. That’s not on you. There are people who will take your words in the worst possible faith, or be short and impatient and skirt the border of being rude without ever technically crossing a line in order to make you feel like you’re the bad guy, and that is not on you and you don’t have to take that.

Don’t write your emails angry, own your actions if you did mess up, try and give people the benefit of the doubt, be sympathetic in a difficult situation, but if someone is being rude & refusing to work with you, you don’t have to apologize just to try and keep the peace. Just because they’re mad doesn’t mean you did anything wrong.

Priority Check – Is This Pressing, or Are You Feeling Pressured?

Jumping off of that pushover check: urgency in someone else’s tone doesn’t always mean the situation is actually an emergency. Sometimes it just means that they’re stressed. In those cases, firing off a quick, “I understand your concerns, and I want you to know that we’re looking at this,” is a good call. This goes back to a core principle: making sure people feel that they’re being heard and taken care of.

However, whether there’s actually a fire that needs putting out is a matter of judgement. When you’re talking to someone who’s close to a problem, their worries may be making them feel like something is the end of the world, even if what’s going on is not time-sensitive and it’s definitely going to be okay.

Remember that even if someone’s stress is making you feel like you should be dropping everything to work on that problem, it may not be the case. There’s an important difference between being responsive, understanding and helpful, and rearranging your priorities because someone else’s stress is stressing you out in turn.

SPaG Check

To make sure all my terminology is clear (hey, gotta put in those details), “SPaG” stands for Spelling, Punctuation and Grammar. This is just about the last thing you do, because if you go back and redraft something, you’re going to have to do another SPaG check once you do. Get the whole thing written and then check the spelling.

This one is honestly pretty self explanatory, since it’s not as intuition-based as everything else I just said. So:

  • Look for red wiggly lines under your words. Sometimes you meant to spell a word like that, but sometimes you didn’t.
  • Look for places where you used the wrong word or phrase, or wrote a word multiple times in a row by accident.
    • If your text editor does grammar checks in addition to spelling checks, then look for blue wiggly lines (or whatever indicator they use). These pick up where you may have repeated a word or phrased something weirdly/incorrectly.
  • If you have any doubts about what a word or phrase means, just Google it & save yourself the stress. It takes thirty seconds.
    • If you have the time and feel like a word isn’t quite evoking what you want it to (see: feeling vague or inaccurate in your phrasing) pull up a thesaurus and search the word you’re using, then use the search results to find the word you want. Don’t use it to gussy up your language unnecessarily, just to try and find the word you’re actually looking for.
  • Use paragraph breaks. Use them liberally. This is both a readability thing & a “making sure they read it thing”: people tend to skim or skip long paragraphs.
    • My rule of thumb is 3-5 lines max, though it varies if you really can’t find a good break. Sometimes I break this rule, but it makes me super antsy. (Look how I broke out this bullet point into its own thing.)
  • Check for really long sentences, or sentences that have a lot of technical info, & try to split them up so they’re easier to parse. This goes along with the paragraph breaks thing — people stop reading stuff that’s too long.
  • Keep an eye out for where you’re repeating words or phrases. If you start one sentence with “However, …” and then do it again two sentences later, maybe change the second one to “That said…”. It creates variety and prevents predictability, which demands attention.
    • (That might be the most pretentious sentence I’ve ever written. Big grain of salt on this one, your mileage may vary, write in your own voice not mine.)
  • Check that you put in all the links.
  • Check that you put in your attachments.
  • If you forget the links and attachments, no big deal, you can send a followup. You can even be a little casual about it (“Looks like I forgot to link this in my previous email, here you go.”) Everyone’s done it, so don’t stress.

Last Little Tidbits

This is the place for the important takeaways and the stuff I couldn’t fit in anywhere else.

First, repeating and rephrasing things that people have said to you makes them feel heard, which makes it easier to help them. (For example, responding to “I’m worried about how many cars will be on the rollercoaster…” with “Regarding your concerns about the number of rollercoaster cars…”). Try to do this before jumping into technical details.

Make sure you know what people want to be called. I’m always hideously embarrassed when it turns out I’ve been using the wrong name (or the long name, if someone goes by a nickname. You can edit this in some systems, like Gmail or our ticketing system, and I particularly try to do this in our ticketing system, since it also future-proofs this for other people.

Once you’ve written your draft, take a second to step back and make sure you’re not making assumptions about what they know. If you’re worried about being too clinical, you can always cut detail later.

If you’re dealing with a known tough cookie, it may also be worth taking a step back and trying to read what you’ve written in a bad-faith light. Having another person take a look can be a huge help, especially since you’ll want to include accurate, honest details so they can’t misinterpret the facts, while not putting in unnecessary info that might confuse or derail the conversation.

Last Thoughts

I said at the top that I didn’t want this to be a prescriptivist checklist, and I mean it. A lot of this stuff is written as instructions, but take them or leave them as you need. Some of it you may already do instinctively; some of it will become easier and easier with practice. Some of it may not work for you, and that’s fine.

Anyway, I’m done revising this. That’s all, folks, and happy emailing!

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