Written Communication

"Maybe in 10 different one-on-ones with people on the team, I had to explain to them a strategic thing that we were doing... Well, you know what? That should probably be a document, right? If the same idea worked for 10 different people... now I'll write that document in 30 minutes and now I have it as a memorialized thing that other people can read on their own time without having to involve me."

"Communication is the job... it is exclusively done through the creation of artifacts or verbalizations that affect other humans. That is all there is."

"One is multimodality... I will give an all-hands and then write a post with the content of the all-hands, because different people are going to respond differently to these modalities."

"It was the writing process itself that actually allowed me to solidify those mental models and those frameworks in my mind. And so I wasn't ahead of the game in any way. It was just I think I really wanted to disambiguate the chaos in my mind about what my job was."

"They were like, "What's your confidence level on your key results? What did you do last week? And what are you doing next week?" And the last week, next week is great because it allows you to start noting down what stops you from getting shit done."

"Whenever I do write something down, I'm glad I did. So I probably do more crystallizing by writing than I would admit."

"Having really smart communication practices is something that I think a lot of companies don't invest in early... Do you have a newsletter? Do you have founders do like a message or a quick video, whether that's on Slack or email. There's a lot of smart tools. You can learn a lot from social media in some ways, but you actually need a strategy for it."

"His advice was write what you repeat. If you say something more than once, just write it down. And then the next time someone asks you, you can just hand them."

"It's the megaphone issue. Someone will pass you in the hall... they'll ask you a question, and as it turns out... people will take that and over-index on what was an opinion... flash tags are literally... an escalating set of what I call the dying on the hill spectrum."

"Stripe had a very strong writing culture. All communication was along from writing business reviews, strategy memos, product reviews... I don't think you can be a good writer, unless you're a clear thinker."

"I take notes in leadership meetings and I share those notes with the whole organization. And that is sometimes it includes candor around reflections on things that aren't going well or problems we need to solve."

"I would say my most successful pitches are three sentences and anytime... Sometimes it needs to be longer than that, and generally I feel like my pitch is weaker for that reason. Attention spans are short, and so the more concise you can make it, the better."

"When I email a reporter, I love to make the subject line just as clear as possible as what the goal is and why I'm emailing them. And so let's say it's for a recurring column that they have, I'll put the name of that column and the person that I think should be included in the subject line."

"To write that post, it takes at least a few days or sometimes even longer. Sometimes it takes a week or two for me to research... I write a first draft. I get some feedback from people who I trust often... And then there's an editing phase where I work with an editor who helps make sure that it's just correct."

"I wrote four or five books' worth of content just last year. It's because I have these deadlines... I also know that thousands of people are paying me, they have expectations of me."

"The best way of doing that is to shut down your laptop, take out a piece of paper, write the question as simply as possible at the top of the paper, and just spend time just thinking about how to answer that question."

"I think business writing, I spent a lot of that time doing that at Amazon, is so valuable because you've got to be a clear thinker to be a clear communicator. And so there's two tests in writing well or communicating well. It's both those things. So I found it's pretty valuable in kind of sharpening your ax."

"Avoid weasel words, answer first and then explain, own your problems... if you can get in the habit early of answering a when question with a date, knowing how to use numbers to answer questions and honestly just learning from feedback and grade yourself after you get feedback on a doc or after a meeting."

"What you want to do is write something that makes it pretty clear to me that this is targeted to me. That's step number one... Don't fake it. People fake it all the time. People email me and they tell me they're fans of my work, they've never read my work. It's very obvious, right? Don't do that. But if you've read something, or if you're familiar with something, if you're familiar with the publication in some way, any signals of that are good."

"The first one is this book here, so Several Short Sentences About Writing... It's an extraordinarily good book about writing and it's all about the sentence, beautifully written, fun to read, really great."

"Every employee goes through actually like a business writing class after they start at Amazon. They give you a little card with five tips that you're supposed to keep on your desk about concision and specificity in the words you use. For example, you should never write the word great in an Amazon press release. You should write user friendly in X, Y, Z way and will save customers time 20 minutes each day through this."

"I remember writing the first draft... and he wrote back, 'This doesn't sound like you yet.' ... I rewrote it completely, and I made it sound like me, and I've tried to make things sound like me since."

"The most powerful takeaway from that book for me was if it's in your head, you're screwed because it's like you're trying to keep track of stuff and be creative and come up with the future of transportation and remember to pick up something from the pharmacy. It's a recipe for disaster. This whole idea of empty mind, beginner's mind, well, you have to empty the mind of all the to-dos first. Just get that out of the head."

"On the communications side, I read some stuff like Minto's Pyramid Principles. Extremely helpful... Whenever I see a great email exec update or whatever, I literally save it in a special folder."

"Novelty, I define, as new idea, so something I haven't heard of before, that's also significant, so it's not some trivial fact about Kim Kardashian, and it's something that I wouldn't have easily intuited on my own. When you have those ingredients, it's new, it's significant, and you wouldn't have easily thought of it on your own, that's when you trigger that dopamine hit reaction"

"I believe that your likelihood to follow through on something you start writing is a function of the objective you have with writing that piece and how strong your motivation is for seeing that objective to fruition... I'll pair one of those objectives that I've selected with a motivation."

"I approach my writing then and I still do now as letters to myself. This is the framework. This is the advice that I need to give myself that I need to go and really do better, and that is what my writing became for me, and it was hugely helpful for clarifying my train of thought."

"I actually like word count goal even better than time goal because sometimes you can spend 30 minutes and then still just produce a sentence, and so, that was always how I approached my writing. I was like, 'All right, I'm going to sit my butt down. I'm going to write for 30 or 45 minutes, but it's going to be, whatever, like 250 words.'"

"I wanted to get better at in the moment communicating more clearly and being just a little bit sharper, a little bit crisper in the points that I had to make... what if I just push myself to communicate in a much shorter form which is going to force me to really strip away all that ornamentation and focus on the core idea."

"Writing is clarity at scale, and a key component to a PM's job is creating clarity both internally and externally... if you can't sell or support your own product, I don't trust you to build the product. And so that's where I think writing is the foundational component there."

"Good writing comes from consuming as much good writing as possible... the more you index towards developing your own taste for what you think is good by consuming others, then you can shift into producing your own and then comparing them and riffing it off other people."

"I think there is a lot of value to saying, 'I need 20 minutes of focused time to interrogate something that I've done. We're not going to talk. I'm literally going to force us into a room or Zoom. You're going to read this doc, I'm going to watch you comment on it in real time.'"

"The thesis is that we're in the midst of a new phase, which is essentially two-way writeups and that's where it's more conversational and feedback and discussion is actually part of the content itself... you have a done reading button at the end of a writeup... making sure that you're actually addressing the most important question... and then probably the most valuable is sentiment or pulse, which is, well, how do you feel overall about this particular proposal?"

"It's called Smart Brevity... I've always been big on writing crisply and being very tight and not having three-page memos that you're sending off. Especially now that we're remote and we're all doing slack and email and different ways of messaging, how tightly you communicate, how crisp your communication is really important."

"OpenAI has such a slack heavy culture and it really... The instantaneous real time communication on Slack is so crucial. And I just love being able to tag in different people from different teams and get everybody coalesced."

"When you write something, read it out loud, literally just read the thing you wrote out loud and half the time you'll realize it's way too complicated... Just say that thing. The thing that you said to me in conversation is the thing you should write."

"The Minto principle is something that I would recommend everyone do, which is put the headline, the full conclusion first and then you're supporting argument second."

"The structure that almost everybody listening in is familiar with is one that comes from the world of advertising. Most advertisements are set up as problem, solution, benefit. There's some problem in the world, here's how we solve it with our product or service, and here's how you benefit from it."

"I really like is a three-question structure: What? So what? Now what? ... What is your product, your service, your offering, your update, your feedback? ... The so what is why is this important and relevant ... And then the now what is what comes next."

"I have CEOs write two-pagers on where did the company come from? How is it different today? What are our external treats to our market? What's our competition? How do you view our competition? What should we care about? What should we not care about?"

"Can I make a presentation I can just circulate on email and everyone gets it? Well, that's called a slide doc. You put more words, you put stronger picture... everything they need to see your thinking, it follows behind it."

"documentation. It's a thing. Asynchronous communication, everyone just has to get used to it and better at it, so increasingly just being better communicators, whether it's on a video or written."

"I actually think especially as you get to more senior positions, writing is the only scalable way of having influence on a larger, larger product org... It's the antidote to that to scale your ability to influence the product direction and maybe even the principles and how you develop product at a company."

"I've actually put a lot of effort in this idea of institutional learning, of doing the quarterly meeting of the most surprising experiments. ... Document it. We had a large deck internally of these successes and failures, and we encourage people to look at them. The other thing that's very beneficial is just to have your whole history of experiments and do some ability to search by keywords."

"I took that to heart. And many of the features that the team presented instead of a PowerPoint, you start off with a structured document that tells you what you need, the questions you need to answer for your idea. And then we review them as a team."

"The idea of the super specific how is that most writers, most course instructors spend too much time on the what and the why and not enough time on how. So if you think about people who are reading your writing, most of them probably already agree with the general premise of what you're saying."

"I have a framework that I call start right before you get eaten by the bear. And the idea is that if you're telling a story about camping, don't start talking about going to REI to buy a Patagonia jacket... Start right before your friend left a Clif Bar out in their tent and you all almost got mauled by a bear. Get to the juicy part."

"more people should learn the craft of writing and the technical aspects of writing, not just look at what other people are doing to try to get audience engagement, but to actually improve your ability to precisely say what you mean and convey the level of conviction that you have and not accidentally mislead people with your words"

"in business, you often want to start with here's my conclusion, and then here's why, versus here's all the things I've done, here's all my thinking, here's all my data points, and then now here's my conclusion at the end of that."

"Being concise is not about absolute word count, it's about economy of words. It's about the density of the insight that you're sharing. And so you can have a 300 word memo that's meandering and long-winded and a thousand word memo that is tight and concise."

"I think the blast radius of a poorly written memo is way bigger than most people think. If you are just shooting off a message in a Slack channel with 15 other people, and it's confusing, you didn't include information you should have included, there's going to be a bunch of back and forth."

"Signposting is using certain words, phrases, formatting, and an overall structure in your writing that helps guide your reader and signals what is coming in the rest of the post."

"I also dislike when people overuse bullets and sentence fragments, phrases in bullets when they should use complete sentences that actually show the connected tissue between ideas, that show the logical flow of what it is that you're saying."

"Clarity comes when you write. So I made them write two-page documents. I'll let you go up to four, maybe. But two page documents with insights, your strategy or I use the word approach sometimes and then the big rocks."

"I really believe in frameworks for things that helps drive extreme clarity. I work on a lot of different projects. A lot of times I'm ramping up a new project, I'm like, "Where can I learn what I need to learn about this project?" I ask five different people, get five different answers. That is unacceptable. Of course, I'm sure there's hundreds of docs associated with the project, but there needs to be one canonical doc."

"I never use bulleted lists because you can never refer to a bullet. I always use numbered lists because you can always in the visual in a meeting as referenced in number two, I have feedback on that, versus the third bullet, two up from the second, whatever, that is not extreme clarity."

"Everyone should know exactly where the canonical doc is. That's the one place I can go to get all the information I need about a project and it will link to all the other docs... The basic information that you need to know is what are the discrete areas of work, I call those work streams... Who are the owners on those work streams?"

"Language actually affects the way you think... when I make slide decks... I spent hours obsessing over them because I really wanted to make sure I captured the right essence of what I was trying to say."

"He doesn't believe in PowerPoint. You write a six pager about ... It's like studying for the final exam is writing these six pagers."

"I feel really strongly that you can write a lot more if you write what you want to write... the biggest strength of writing what you want is you get to write where there's energy and you don't have to write where there's no energy, which takes you really, really negative."

"If your goal is to write a lot consistently over time, my biggest advice would be just publish. And so there's a lot of people out there with stuff that hundreds of drafts and they've not published anything. And my thing is I publish almost everything I write."