Async Collaboration: How to write well at work

Async Collaboration
How to write well at work
By Brie Wolfson 
🐦 @zebriez 
👀 koolaidfactory.com 
✉️ brie.wolfson@gmail.com
🐌 Quick on the summary, slow on the edges
The stuff everyone already knows/agrees on is important context and might help tee-up your writing, but it isn’t the most interesting thing about it. 
Get the state of/summary out fast so that you can spend the majority of time on the more controversial, lesser-known, lesser-considered, bits. 
📝 Edit like it’s going out to 4,000 readers
If you’ve ever worked in email marketing, you know the terror that is hitting the big green ‘send campaign’ button. Before you hit send on any piece of writing, imagine thousands of people were going to read it then edit like you’ll be punished with a pile of emails if you’re not crystal clear. (If I can, I’ll ask at least one other person without context to read it to help!). 
This could be anything from typos to broken links to factual errors to unclear phrasing to weird language. Then, I edit like I will be punished with a pile of emails if I’m not crystal clear. Because, hey, you might be.
😃 Be positive and enthusiastic
Great writing often starts from a place of pain. But the hole-poking, tear-it-to-shreds kind of writing isn’t the most effective if you want to get something done. It’s tempting, and potentially a good place to start, but challenge yourself to go a step further. 
Use that thorn in your side and write with positivity, enthusiasm, and optimism about what can be done instead of what can’t. Something that orients towards solutions with an upbeat tone will make others more likely to want to learn from you and work with you. Make your writing a source of light, not darkness.
📜 Use metaphors, similes, stories, and examples
When it makes sense. This helps you be memorable and it adds texture to the piece. It also helps you avoid platitudes. I’ve found these are particularly helpful when you want to build empathy, bring something to life in a new way (especially if the original idea might feel dull), change minds and behaviors, explain something that is a little esoteric.
🌈 Panache, personality
The weird quirks and isms that your friends like about you is exactly what you’ll reader will like about you. Have a voice. Have a personality. Do it with penache. It’ll make reading more pleasant, make you more memorable, and in turn, increase the likelihood that the ideas stick and that they stick to you as the author. Don’t be overly chatty or punchy, though. That can be a little irritating. 
4️⃣ Write with four people in mind
This is not four imaginary people or archetypes of people (ex- B2B enterprise CEO, ecommerce user in Brazil) but rather four very specific people (ex- Tara, the product manager on the billing product with a knack for Nike sneakers, or Gregoire, the CEO of our largest user in France). Ideally, you’d pick people that are in your target aspirational audience for the writing; someone who will be interested but be particularly discerning. 
Now, before I write anything, I write four names at the top of my doc. When I think the piece just about done, I refer to those names and I imagine them reading. How would they react? What would they expect more of? Less of? What would they tell me to amp up? Tone down? What would they roll their eyes at? What would pump them up? And then, I edit, edit, edit.
👀 Get someone else to read it before you publish
Ideally, get a few people. I’d suggest 1-2 people that you want to impress/that you think would definitely read the piece once it was published and 1-2 people that you don’t think would be naturally drawn to the material/aren’t familiar with the subject-matter, but might enjoy it anyway.
🙌 Talk up to your reader
Respect the intelligence, resourcefulness, and curiosity of your reader. Referencing a complex idea or technical specification is appropriate if it is the best way to get your point across and/or connect with your audience.
If your reader doesn’t know what it means, trust that they’ll put that intelligence, resourcefulness, and curiosity to good use and figure it out. Along these lines, assume that someone who might not agree with you are just as intelligent and thoughtful on the topic. Thinking of your skeptics this way will only enhance the quality of your writing–if you can persuade even your toughest critics, your writing has done its job.
🤸 Don’t be stuffy
From The Economist’s Style Guide: “To write a genuine, familiar or truly English style”, said Hazlitt, “is to write as anyone would speak in common conversation who had a thorough command or choice of words or who could discourse with ease, force and perspicuity setting aside all pedantic and oratorical flourishes.” 
Use the language of everyday speech, not that of spokesmen, lawyers or bureaucrats (so prefer let to permit, people to persons, buy to purchase, colleague to peer, way out to exit, present to gift, rich to wealthy, show to demonstrate, break to violate). Pomposity and long-windedness tend to obscure meaning, or reveal the lack of it: strip them away in favour of plain words.”
💬 Start with normative observations, then reflections
State truths; the exact things that happened. This includes both inputs and outcomes. 
Then, editorialize them.
My three favorite style guides
My Favorite Style Guides
The Economist's Style Guide
Do not be stuffy

Use the language of everyday speech, not that of spokesmen, lawyers or bureaucrats (so prefer let to permit, people to persons, buy to purchase, colleague to peer, way out to exit, present to gift, rich to wealthy, show to demonstrate, break to violate). Pomposity and long-windedness tend to obscure meaning, or reveal the lack of it: strip them away in favour of plain words.

“To write a genuine, familiar or truly English style”, said Hazlitt, “is to write as anyone would speak in common conversation who had a thorough command or choice of words or who could discourse with ease, force and perspicuity setting aside all pedantic and oratorical flourishes.” 

Do not be hectoring or arrogant

Those who disagree with you are not necessarily stupid or insane. Nobody needs to be described as silly: let your analysis show that he is. When you express opinions, do not simply make assertions. The aim is not just to tell readers what you think, but to persuade them; if you use arguments, reasoning and evidence, you may succeed. Go easy on the oughts and shoulds.

Do not be too chatty

Surprise, surprise is more irritating than informative. So is Ho, ho and, in the middle of a sentence, wait for it, etc.

Do not be too didactic

If too many sentences begin Compare, Consider, Expect, Imagine, Look at, Note, Prepare for, Remember or Take, readers will think they are reading a textbook (or, indeed, a style book).

Strunk and White's Elements of Style
Use the active voice

The active voice is usually more direct and vigorous than the passive. 

“This region was surveyed in 1900.” over “A survey of this region was made in 1900.”

“These reports cannot be confirmed.” over “Confirmation of these reports cannot be obtained.”

Put statements in positive form.

“He usually came late.” over “He was not very often on time.” 

“He thought the study of Latin useless.” over “He did not think that studying Latin was much use.”
George Orwell’s Politics and The English Language
Never use a long word when a short one will do. 

If it’s possible to cut a word, always cut it out.

Never use a foreign phrase, a scientific word or a jargon word if you can think of an everyday English equivalent.
Favorite Writing Resources
The Pyramid Principle
Barbara Minto
Working Backwards: Insights, Stories, and Secrets from Inside Amazon
Colin Bryer & Bill Car