I had to write emails every day for 4 years in a high-pressured sales environment. During that time I screwed up a lot. I let my emotions show in emails, made the mistake of being too casual, and sent novella-length emails that were probably never read and should have been conversations in person.

I pissed people off, wasted time, and pressed “send” by accident one too many times.

Eventually, with lots of trial and error, as well as real-time feedback, I got better. Towards the end of my 4 year stint at my previous company I certainly wasn’t starting any fires. Well, at least not by email.

Here are 38 lessons I picked up along the way. Some of these are related to my line of work but most are applicable across industry.

Always say thanks. People’s blood sugar levels are constantly fluctuating as the barrage of messages flood in. Simply showing your appreciation at the end of each email, especially when someone has taken the time to help you with some thing (however small) is a step to building trust. These add up over time and good karma will come back to you.

Cut out one word from each sentence. The purpose of writing is to get your point across, not to send cryptic messages or practice your literary prose. After you finish your email systematically remove one word that you don’t need. Trust me, it’s there.

Cut out one sentence from each paragraph. Similarly, if you find yourself writing more than 3 or 4 paragraphs, you should ask yourself if they’re really necessary. Systematically remove paragraphs that are redundant. Shorter the better. If you feel like you can’t, ask a colleague to check it for you.

Don’t give ultimatums. When you are stressed to meet a deadline and need to convey this in an email, the key is not sounding threatening as you risk disrupting the entire relationship. Sending a client an email saying “Please respond immediately or else we will have to reconsider our terms” might be acceptable as a final straw, but often I sent this too soon. Using decisive but soft language is usually more effective— “The final deadline for this contract is approaching on X date, which won’t be possible to extend. I’m looking forward to receiving your confirmation shortly and feel free to call me at…”

Never reply when you’re upset – wait 24 hours. The biggest regret in my career of email-writing has been sending that emotional “I’m important and pissed-off, so listen to me” email. Take 10 deep breaths, get away from your computer, and look at it tomorrow. The greater your anger, the greater the wait period. If the email doesn’t totally upset you, but just irritates you, then come back to it an hour.

Ask a colleague to double check if it’s an important email. Find a colleague that isn’t scared to give you direct feedback. A fresh pair of eyes is always beneficial.

Be careful about CCs — dropping and adding randomly or passive-aggressively. Be conscious of who is on a CC, as sometimes they will be important to the email chain and if dropped unknowingly can annoy others. Also, don’t drop people from CC on purpose without saying so. I usually put an astrix at the bottom or top of the email when doing this in smaller letters, *removing John from CC as not to flood his inbox.*

Use CCing as a negotiation tactic. On the other hand, CC’ing can come in handy when you’re not getting any response or traction from your point of contact. Like the time an HR director from Airbnb ignored me for a month, I CC’d Brian Chesky and they responded with 5 minutes. Huh, funny how that works.

Ask: Is it worth it? Do I send this email? Whether it’s feedback, a question, complaint, request, negotiation or otherwise, sometimes we forget what’s at stake. How will the relationship be affected if I send this email? Sometimes the issue can be brought up at a later time or in person.

The cardinal rule: you will get more emails if you send more emails. In an ongoing effort to reduce my inbox, I simply sent less emails. It worked.

Enable the unsend/undo button. This function in gmail is an absolute lifesaver. I believe you can set it from 10 second to 1 minute intervals. I would yell “oh sh*t!” and press undo almost daily.

Spell check. While it’s very superficial, unfortunately people do judge you on grammar and spelling. Try not too make too many errors or else people will think you’re drinking or incompetent.

Categorize priority – end of day, end of week, etc. I get newsletters and interesting stuff that I read at the end of the week. Other emails aren’t urgent and can wait a few days. Make sure you have a system (I simply starred emails that were important) that works for you. You don’t want to be spinning wheels responding to and reading low priority emails all day.

Shit sandwich – consider it. When delivering feedback the classic management technique never fails to disappoint. “I liked this, but X needs improvement, oh and Y was a nice job!” The bad stuff in between two slices of good. Remember, you should be giving more thanks and praise than negative feedback or else the ‘feedback jar’ becomes overflowing with shit and people will pick up on the stench.

Are there questions in your email? Why not? Emails can turn into declarations and statements rather than two people actually communicating. Especially when dealing with an unfamiliar person by email, you tend to have very little context. Don’t assume anything.

Should this be in person or by email? This is the million dollar question. Are you flushing out the details of an idea or project and find it is communicated more efficiently by email? Or are you hiding behind a screen because you don’t want to have a difficult conversation?

Never be mean — it will bite you in the ass. Life is short and there’s already enough misery in the world, why make it worse? As the saying goes, people won’t remember what you said but they’ll remember how you made them feel.

Make it easy to read with different colors and spacing. When emails get long, no one wants to read big blocks of text. Space out your points, cut the fat, and if you’re replying to a long email with various questions then change your answers to a blue color in-line so it’s easier to read.

Don’t spend too much time on it. When someone would send me an email saying ‘thanks’ or one that didn’t need a response, a still felt this urge to respond. I would sit there and wonder what to say, even though anything would have been excessive. Know when an email chain has ended and don’t feel obliged to continue a conversation that has concluded.

Spend a lot of time on it. When there’s a lot at stake it’s best to put some time, a 2nd/3rd pair of eyes and few re-reads before you send it off. Print it out too.

Ask yourself: why am I sending this email? What’s my goal? Often times we are looking for something or want to request something but are too wishy-washy. There’s no action point and we expect people to read between the lines. They don’t. Clarifying your own goal allows you to clarify to others.

Don’t approach it as a checklist/reactively. Prioritize. ‘My goal today is to clear my inbox!’ is not a strategy. Your job description doesn’t (at least I hope not…) include “clear inbox daily.” Something went wrong in your email prioritization.

Don’t send emails on the weekends. Unless it’s an emergency, but it rarely is, and if it is you should call them. No one wants to read your email on a day off and you’re just creating unnecessary stress. You can still write it up, but use the Boomerang app to schedule the email for Monday morning.

Don’t open email if you have to sleep. Turn off notifications. That is, unless you want to spend hours staring at the ceiling thinking about the future which you cannot control and dream about work. I put my phone in airplane mode in a separate room.

Acknowledge a response even if you don’t have a long response (“I saw this and will get back to you in the next 2–3 days!”). Especially if you think it’s going to take you some time to get to the email, don’t leave them hanging. A short message of acknowledgement and perhaps even timeline will manage their expectations.

Don’t read email while talking to people. Our brains are bad at multitasking. You’ll inadvertently mix up your email or send it to the wrong person. It only takes one instance for disaster to strike.

Don’t judge someone’s personality based on an email. Unless you have a long-lasting relationship with the emailer and have a good sense of their personal language, humor and phrasing, it’s best not to jump to conclusions — ‘he’s an asshole or he’s so boring.’ There are too many unknowns.

Negotiating contracts by email is easier than in person. There are exceptions, of course. But I found that especially when it came to contracts, it was much easier to remove the emotion from negotiation and just speak in terms of facts and priorities. If done in person we potentially slip into reactive/emotional responses in particular as a lot is on the line.

Every month clean up subscriptions you don’t actually read. At one point I remember coming to work and spending the first 10 minutes clearing junk…the same junk every day. It was like some mind-numbing pleasure or more likely procrastination. Eventually I just unsubscribed from the trash.

Go one day a week not checking emails. Turn it off and go for a walk in the park. See friends, have a good conversation, get some sunshine. Your happiness goes down as the amount of time on email goes up.

Don’t keep your email tab open, or else you’ll read it. Email is the biggest distraction of the 21st century. Actively remove it from your work when you actually have other stuff to do, or else your dopamine receptors will be firing in anticipation of some oh-so-important email from Jim.

Don’t be obnoxious about using bold and italics and underlining. It’s patronizing. When I wanted to emphasize a point I would go overboard. People aren’t dumb, they’re reading your email already. If something is important, say it’s important. Bold and italics should be used mostly for organizing your email and headings.

Call or ask in person instead. Colleagues sitting next to me would email me with questions when they could have just asked me in 2 seconds. Other times I would be banging my head trying to word an email professionally when I could have just picked up the phone and asked the same question in the exact tone I wanted to convey. Don’t over complicate it and don’t over-rely on email.

Don’t use big words. I would be insecure when talking to big and important people. But I found that the higher up they were, the simpler language they used. The just want to get their point across and have no time for fluff.

Be aware of your audience. Switching back and forth between communication styles is tricky and requires you to take 2 steps forward. Before pressing send simply ask, “Knowing what I know about this person, how will they react?” Anticipate their response, then re-rewrite your email to make it more thoughtful and specific to the receiver.

Smileys are OK. Depends on the audience, but I think nowadays people don’t care so much. Use sparingly though, maybe once every 10 or 20 emails.

Saying Hi with an exclamation point makes you sound like you’re asking for ice cream. I cringe when people send an email with HEY! or Hi! Maybe it’s not a big deal. Also stop using so many exclamation marks. It’s hard to take you seriously.

Share something useful by email without expecting anything in return.Sometimes you don’t have to ask for something or expect a response. A good deed is a good deed…Karma builds up and the universe will repay you one day.

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