Editor’s note: I originally wrote this document for a workshop with David Perell’s Write of Passage. Thank you to everyone that attended for being so engaged and thoughtful. Your questions, stories, and ideas are reflected in this updated, and much-improved, version.

A Culture of Writing

I’ve come to believe that Stripe’s culture of writing is one of the organization’s greatest superpowers. As startup whisperer, patio11 puts it, “Stripe is a celebration of the written word which happens to be incorporated in the state of Delaware.”

Half of the story of what makes this so would be obvious to onlookers–Stripe has always treated documentation as a first-class product. People from every corner of the company author blog posts. The company publishes a magazine about building and operating software (Increment) and books about technological and economic progress (Stripe Press). But what most people don’t see is the massive library of content produced inside the company for Stripe-employee-eyes-only. And that’s where I think the real magic happens.

People say the same about many of the great companies. Books have been written about Amazon’s writing culture. There’s an entire section in their 2017 Shareholder Letter dedicated to espousing the benefits of the Six-Page Narrative. Bill Gates already had his finger on this pulse in 1999 when he published The Speed of Thought: Using a Digital Nervous System. The entire essay is worth reading but the gist on his take on why writing is important is this:

“A collaborative culture, reinforced by information flow, makes it possible for smart people all over a company to be in touch with each other. When you get a critical mass of high-IQ people working in concert, the energy level shoots way up. Knowledge management is a fancy term for a simple idea. You’re managing data, documents and people’s efforts. Your aim should be to enhance the way people work together, share ideas, sometimes wrangle and build on one another’s ideas–and then act in concert for a common purpose.”

Many Stripes that go on to found companies make writing a core part of how their company operates–Cocoon has “we write things down” as one of its four values on their jobs page. I don’t know a single Stripe that hasn’t advocated for implementing Stripe’s email transparency norm at their next company. I’ll also add that many Stripes that move on from the company and find themselves at companies that don’t embrace the written word to the same extent. I count myself among them. We all report feeling a bit lost and disconnected from their colleagues without it. This is all especially true in the remote work environment. When we catch up over coffees and meals, conversation often drifts to how surprised we are that a 200 person company can feel so big when Stripe still felt so cozy even as we crossed the 1,000 employee mark. We, somewhat embarrassingly, talk about how much we miss reading a great shipped email.

Through my work on The Kool-Aid Factory, founders often ask what steps they can take to cultivate a culture of writing in their companies. Like any cultural norm, if it’s going to stick, everyone’s got to find their own way of embracing it. And that requires setting up infrastructure that anyone, in any corner of the organization, can plug into and rely on.

So, here are some ways anyone can start wielding the proverbial pen. Consider this your invitation to get writing!

Table of contents:

• Thinking in papertrails and curations
• Papertrails
• Curations
• A system of editors
• A quick note on distribution
• Bonus: Other docs I keep, mostly for funzies

Thinking in papertrails and curations

Writing shows up within a company in two primary ways: papertrails and curations. Papertrails are documented accounts of what happened, typically produced in the run of work while it’s happening. Meeting notes are the most obvious example. Curations are artifacts of work produced to contribute to the system of shared knowledge. These are typically editorialized summaries of work that has already happened or an outlook on work that will happen soon. The audience for curations is those who might not naturally encounter the work, but might benefit from knowing or understanding more about it. A 6-Page Narrative at Amazon would fall into this bucket.

A reliable papertrail system:

• Feels like a well-enforced virtual open door policy. People feel welcome in the conversation on things that affect or are affected by their work.
• Keeps the record straight. Not even a simple message can survive a game of telephone in an organization. Getting things down on paper ensures that everyone has the same understanding of what actually happened.
• Supplants and improves meetings. When there is good documentation around a meeting (briefs, meeting notes, etc.), meetings can be leaner and more productive because people don’t have to be in the room to know what’s happening. So, only those who are actively contributing to the discussion need to attend.
• Connects practitioners to the work. Those who produce the work have control over how it is represented. Papertrails also provide an opportunity for backlinks to the work itself. No one has to summarize or represent your work for you.
• Makes the company less-political. Take it from Succession’s Kendall Roy, master of Machiavellian tactics, “words are just, what? Nothing. Complicated air flow.” Without meeting notes and documentation, companies become reliant on unreliable verbal accounts, 1:1 updates, and needing to be in the room to get things done.

A reliable curation system:

• Democratizes ideas. Anyone with an insight or idea can write it down regardless of status or access. And, anyone can read writing, regardless of status or access. Great ideas will bubble up. I’ve seen documents written in a corner of an organization make their way all the way to the CEO and meaningfully influence top-level decisions.
• Is a forcing-function for thinking and communicating more clearly. Have you ever had the feeling you know a thing inside out, but then as soon as it comes time to talk about that thing in a meeting, the words come out all wrong? I have. In those moments it can be hard to tell whether the gap in clarity is in the idea itself or the communication of it. But the truth is, in the work context, it doesn’t matter. When you codify ideas in a piece of writing, you also codify your thinking.
• Is a forcing function for thinking more globally. When the potential audience for something is ~everyone at the company, team members are much more likely to incorporate more perspectives and wider-reaching implications.
• Makes the hivemind go buzz. Team members can self-serve on making connections across work and each other. They don’t need managers or a meeting or another intermediary to do it for them.
• Makes it more satisfying to get the work done. The inquisitive, context-seeking team members typically end up producing better work and working better with others across the org. This creates a positive feedback loop system. The work gets even better and it feels more satisfying to do it.
• Is a job perk! Patio11 calls access to the library of documents “his favorite job perk”! In the time you normally spend scanning Twitter, you learn a whole heap from your brilliant colleagues about the work they are doing right next door. You can feed your curiosity and level up, for “free,” by diving in deep on anything anyone at your company is working on.

The most common resistance to this approach is the time investment required to produce it. People may say writing is “metawork.” But I say give it a try. The throughline on all these benefits is more organization-wide trust. I can’t think of a single greater driver of organizational efficiency than trust. And I can’t think of a faster, more reliable way to get there. 

So with that, here are some examples of writing you can produce and encourage others to produce in each of these buckets.

They’re accompanied with best practices to consider, anecdotes that bring their implementation and benefits to life, and templates to help you get going fast. The documents I’ve found particularly high-leverage have an *, and may be a good place to start or experiment.

 

 

Papertrails

When you’re producing any papertrail:

• Bias towards normative descriptions/observations over opinions/editorial. Remember, the goal is to keep the record straight for all.
• Make sure everyone that’s represented cosigns any artifact before publishing ‘publicly’
• Remember that these run orthogonally to the writing done to advance the work–emails, Slack messages, JIRA tickets.

 

*Meeting Notes

• Taking notes in a meeting is perceived to be a low status job, but I don’t think it is. Not only does the notetaker control the narrative, it also decisively puts your name on the work.
• Anecdote: Former Secretary of State Madeleine Albright credits her career jumpstart to her diligent and reliable notetaking.
• Template: I share meeting notes with three sections: 1/ decisions 2/ actions and 3/ Brie Editorial (where I share more personal commentary/musings/impressions)

Meeting Agendas

• Do everyone a favor and require these for meetings. If you’re running the meeting, but sure you have one. If you’re asked to attend a meeting without one, ask for it! 
• Sending a meeting agenda signals to your colleagues that you value their team and helps them better prepare.
• If shared context is required, try a drafting memo and starting the meeting off with a silent reading period.
• Template: Start the meeting by stating “we should not leave this room without x” Before the meeting ends, check back against your meeting goal

FAQ’s

• If you get the same question 3 times, it’s probably time to document the answer somewhere. That way, your colleagues can self-serve on finding the information they need to do their work. It saves everyone time!
• Anecdotes:
  • I published a document of frequently asked questions about Stripe Press to the company. This included why we do this, how much we spend on it, how we source our books, and more. This helped others better understand talk about our work on Stripe Press in a consistent way, which was especially important for a project that, at first blush, seemed potentially orthogonal to Stripe’s mission.
  • Stripe’s early User Support teams kept very detailed FAQ docs, including canned responses to common questions, that anyone on the team could contribute to. These became useful to all user-facing teams including Sales, Account Management, Partnerships. They also became useful to product, engineering, and design teams because it helped them understand where users got tripped up. One particularly prolific and talented Support Engineer shared a weekly log of insights and learnings after untangling some of the gnarliest issues. These were read widely across the company (including by the leadership team)

Snippets

• This is a simple account of what you, or a group of people, is working on.
• Have a template that everyone uses. Potential formats include a few bullet points or PPP’s (progress, plans, problems) or 5:15’s (named as such because it should take no more than 5 minutes to read and 15 minutes to write.)
  These should be a combination of how things are objectively going and how people are feeling.
• Anecdotes:
  • Patagonia founder, Yvon Chouinard, pioneered the 5:15 format.
  • In 2001, when Google was about 400 people and had a recently-established management layer, Larry Page relied on manager “snippets” for a report of what teams were working on. After digging into the snippets of the IC engineers one level down, he found that something wasn’t adding up. He decided to fire all the managers.
• Snippets Template

 

Out of Office Coverage Plans

• As time away goes up, so should the level of detail in your coverage plan.
• Decide for yourself whether you will be hard offline or lightly checking in (hard offline is usually recommended to get the full benefit of the time off). Then, make sure you are setting appropriate expectations with your stakeholders.
• Share a light (but humble!) reference to how you are spending your time away to help show a bit of your personality (ie- in the mountains, in a cabin reading, going swimming, etc.).
• A few guidelines to consider:
  • No one’s name can go onto a coverage plan without their explicit consent.
  • Anything that can wait for your return should. There’s no need to place undue burden on anyone else in the organization.
    Request coverage from the person that has to do the least amount of work to cover you (ie- someone who already has context on the work).
  • Have a single point of contact to help route requests beyond those.
  • If you are the sole owner of something that, if it breaks, could hurt the company, make sure there is active coverage.
• Out of Office Coverage Template

*Decision Logs

• This is simply a record of the decisions that impact the team. Publish these wherever your team actively communicates: Slack, team meeting agenda, etc. and then keep a running log documented elsewhere (ex- company/team wiki)
  • Consider setting up a ding word for these logs so that team members or onlookers can opt-in to notifications about decisions that might affect their work.
• Bias towards over-logging to start, and refine over time as more trust is established.
• This may invite questions or push-back on decisions, but embrace this discourse and treat it as an opportunity to explain the ‘why’ behind the ‘what’ and bring your colleagues along with your work and thinking.
• Anecdote:
  • Many of Stripe’s most effective and efficient Product/Engineering teams published decision logs into their team Slack channels–even if the decision was a small one. Many teams adopted this practice over time.
  • Investor Sam Hinkie advocates for “Decision Journals” in his line of work. He says, “a way to prop up this kind of humility is to keep score. Use a decision journal. Write in your own words what you think will happen and why before a decision. Refer back to it later. See if you were right, and for the right reasons. Reading your own past reasoning in your own words in your own handwriting time after time causes the tides of humility to gather at your feet. I’m often in waist-deep water here.” (h/t David Perrell)

Curations

When you’re producing any curation:

• Make these a joy to read so people actually read them. Think about someone deciding to read this over their morning cup of coffee in place of scrolling Twitter or TikTok.
• You never really know who at the organization should or would like to know about the work. Curations offer an opportunity for anyone to self-serve on plugging into your work. Sometimes, plugging in will be useful to the company or business in some way (for example, someone identifying a use-case for something you’re doing you didn’t even consider). Other times, it will be an opportunity to make a connection with another person in another corner of your organization (for example, someone has a specific skill, insight, or affinity for something you’re working on).
• Use these documents as an opportunity to show your personality, too. It’ll most likely make your document more enjoyable to read and also provide another vector for potential connections to your colleagues.
• Be consistent and particular with the words you use to describe your work. Use quippy words and phrases that will help people repeat things in a way that appropriately reflects your work when you are not there.
• You’re improving visibility on your work while also signaling ownership and care.
• Unless something is explicitly produced to be an ongoing reference document for others, consider these a snapshot of a moment in time. This means there is no real burden to keep these updated.

*The story of a thing you shipped

• Ideas for what to include:
• Context: background, motivation
• What shipped: project/product details, where to look (website, API, blog, etc.), how to use it, also what didn’t ship/why
• Under the hood: cool things to know (for our eyes only) about the process of getting this out-the-door
• What’s next: what we hope to see, asks of readers if there are any, where to go to follow along, ask questions, or get help
• Team: thanks to contributors

The state of a workstream you own

• A thorough representation of how the work is going. Include
  This can often preempt questions or vague curiosities from others, and can help your work get on the radar of company leaders without needing face time. In other words, it prevents people from asking that icky rhetorical question, “what does $person even do all day?
• Experiment Kickoff and Results Template
• Business Review Template

*Observations about something you know/care about

• This is your chance to show your stuff and how deeply you think/care about something. Only publish these if you really, really know what you’re talking about.
• These can be shared with the entire company or shared directly with someone close to the work.
• Anecdotes:
  • Stripe ending Bitcoin support started as an internal memo.
  • I’ll never forget this thing patio11 said to me early in my career “grab more stuff and do it. Tell us what you see and think. People will get on the Brie train.” He was right. Soon, I started an internal newsletter focused on industry news relevant to Stripe’s interest. This garnered the attention/praise of Stripe’s co-founder and President, John. I also published a memo on an experiment I ran with my team on how we evaluate candidates. This garnered the attention/praise of Stripe’s COO, Claire.
  • An employee with a surprisingly good rapport with the Stripe CEO reveals he sends an email to him every Sunday.
  • patio11 called the one I wrote for Stripe Press a “crackling memo about the current state of book publishing” and it helped him advocate for me and the work.
  • Bill Gates’ New Rules’ states: “I read all the e-mail that employees send me, and I pass items on to people for action. I find unsolicited mail an incredibly good way to stay aware of the attitudes and issues affecting the many people who work at Microsoft.”

Kickoff

• Let people know that you are getting started on something so that others can chime in in helpful ways before it’s too late.
• Anecdotes:
  • I published a kickoff document about Stripe’s renewed focus on editorial (at the time comprised Increment magazine, spinning up Atlas Guides, getting more people to contribute to the company blog, and a few other internal initiatives). Knowing that the company cared and that there was support for doing it got more people interested in writing. One of the first pieces we worked on was a blog post about the company wiki, which ended up being the third most-viewed blog post of all time when we launched
  • I published a Stripe Press kickoff document with a section titled: The Search for the Right Approach to Author Payment. It was not only an artifact of how deeply I was thinking about something, but a bat signal for those that might be able to help. It turned out that another Stripe had started an indie record label and had some great ideas/research/experience that informed our approach.
• Project Kickoff Template

Retrospective

• While this is an account of something that already happened, they should be ultimately forward-looking.
• Do this for work that succeeds as much as work that doesn’t
• The more intellectually honest, the better. Sometimes, having a neutral facilitator helps everyone get there.
• Try the simple framing of: things we should “stop, start, and continue” doing when it comes to this work.
• Anecdote: Figma and Stripe were both excellent at retrospectives when it came to incidents (example from Figma’s blog, an external artifact of an internal discussion, here). Doing these helped keep trust up with our customers and helped teams stay connected and on each other’s side, even when things hit the fan.
• Retrospective Template
  

*Feedback for colleagues

• People are really good at remembering how others perceive them, and even better at how you make them feel. Help your colleagues build their own self-awareness about what’s so particularly spectacular or challenging about working with them
• I do my best to do a really, really great job on these. Use specific examples. Go deep. Be direct. Don’t be generic. Take time to pick the right word.
• Anecdotes
  • Uber employed a lightweight structure they called T3/B3 (short for Top 3, Bottom 3).
  • Kayak founder, Paul English, pioneered the 5-Word Performance Review. It’s exactly what it sounds like. In this instantiation, concision is the path that makes them not only easier to produce, but also easier to digest. In his words, “I want to be really clear that these are the things that we love about you and these are the things that suck.”

Self-review

• Companies often have a formal process for doing this. Whether it does or does not, I’m a big fan of the personal reflection as a tool for growth.
• Consider sharing this with those you work with closely, especially if there are ways they can help you.
• Anecdote: David Singleton’s Founders Journal has a section for tracking your satisfaction on a given week according to how you rate your week on the following dimensions. For me, it’s a great mechanism for keeping me honest on how I’m actually doing over time.
  • 1- enjoyed it
  • 2- got stuff done
  • 3- progressed goals
  • 4- learned
• Template: I like to do these in three sections.
  • 1- where I believe my particular working style and skills are contributing to my success or holding me back
  • 2- where believe the infrastructure at the company is contributing to my success or holding me back
  • 3- asks for how those around you can help you grow and stay accountable

 

A system of editors

It’s easy to look at a piece of writing and assume that the words flowed straight from the authors head, through his fingertips, and onto the page just like that. In reality, though, all great writing has been poked and prodded and tweaked and twisted into the prose you see on the page.

If you want great writing, you’ll also need a great system of editors that help bring the author’s ideas to their full expression. That means getting your great writers, communicators, and domain experts involved in the writing process.

Editing can be a tough, thankless, job though. As Maxwell Perkins, editor to Ernest Hemingway, F. Scott Fitzgerald, Marjorie Kinnan Rawlings, and Thomas Wolfe, says “an editor does not add to a book. At best he serves as a handmaiden to an author. Don’t ever get to feeling important about yourself, because an editor at most releases energy. He creates nothing.” So, it’s all the more important that there are processes in place that recognize and value the work of the editor.

Here are some ideas for what those could look like:

Red Pens

• This group can either be appointed or trained up. Consider biasing towards the former to start, and then having that team design the training for others.
• Working with this group can be opt-in or required. Taking the feedback can be optional or highly encouraged. The scope of this group can expand to approvals, too.
• This group shouldn’t be limited to people that have writing in their official job title, but they should all be great wordsmiths and upholders of the company tone. The more functionally diverse this group is, the better positioned the group will be to serve the many, many things your company will publish about.

Writing Review Channel

• Create a way to reach Red Pens or others that can help with writing. This way, authors or aspiring authors have a reliable channel for getting feedback.
• For asynchronous editing, this could be a Slack channel, Email List, Slack Ding Word, or workflow in your ticketing system. Editing naturally lends itself to async review.
• For synchronous editing, this can be office hours that people can sign up for.

Braintrusts

• Groups of people with a particular domain expertise that can provide feedback on writing in those topic areas.
• Working with this group can be opt-in or required. Taking the feedback can be optional or highly encouraged. The scope of this group can expand to approvals, too.
• Anecdotes:
  • The Pixar Braintrust meets every few months to evaluate movies in-progress. In the words of Ed Catmull “Its premise is simple: Put smart, passionate people in a room together, charge them with identifying and solving problems, and encourage them to be candid. The Braintrust is not foolproof, but when we get it right, the results are phenomenal.”
  • At Reddit, employees organized into topic-focused “guilds” (ex- ML, Kubernetes, Frontend) that met every two weeks. The goal of the meeting was to broadcast learnings/best practices and get early feedback on ideas/projects.

A quick note on distribution

Documentation only gets organizations half of the way in building the system of knowledge shared. Nailing distribution (ie- ensuring the right people can find the information) gets organizations the rest of the way.

To do that, here’s a menu of options to consider for company-wide comms channels that can help improve visibility and context on work across the company. They are all designed such that everyone can contribute and/or follow along. I’ll write more about this soon.

 

Feedback?

What resonates? What are you skeptical of? How have you seen this play out, or not, in your experience? Where would going deeper with stories and examples help paint a picture?

I’d love to hear your thoughts!

 

Bonus: Other docs I keep, mostly for funzies

• Brag document: I call mine “what Brie is proud of” and it includes things I did and things others have said about me or my work that makes me smile. This has helped me establish an actual pulse on what I like/don’t like, versus what I want to like. For example, early in my career, I thought I would go a data/analyst direction. But, I realized after well-documented accounts of what I’m proud of that nothing analytical always showed up. I took a different course!
  • Read Julia Evans’ post on the topic here.
• Personal OKR/Shipped List: An OSR (ongoing/objective stack rank) is simply a list of all projects in the order you will do them. I also include any signs of ongoing impact that can be attributed to these ships. I love this format because:
  • It helps see the forest for the trees. In other words, it’s a great reminder of the overall shape of my work and how it all fits together to drive broader impact (beyond the daily slack messages, emails, meetings).
  • I look at my OSR at the start to my week to create my to-do list; it ensures sure I’m driving major workstreams forward proactively alongside any reactive work.
  • Since time is zero-sum, having an OSR forces me to confront what existing work gets bumped to make room for new work
  • It’s a great tool for a manager 1:1 because it helps: clearly display what I’m working on (and not working on), my manager to point to a line item if she wants dig in, me add new work responsibly
  • It’s lowers the activation energy of identifying big things to work; it’s just the next thing on the list
  • It turns into a detailed record of what you’ve shipped
  • OKR Template
• Note: These two documents combined make self-reviews a cinch.
• What I learned today: A personal FAQ of sorts. Transcribing something usually helps me internalize it better. This turned out to be the first doc I produced that got noticed by a leader at Stripe. The then COO, Darragh Buckley, asked if he could share it with the company as a reference.
• Re-writing my job description: what I actually do. I re-write this every 6 months or so and talk to my manager about this. Something that’s so exciting, but also challenging, about working in a startup environment is that as the company grows and changes, so does what’s required of the individuals in it. Keeping tabs on how your role is evolving helps you (and those supporting you and your development) ensure it’s moving in a direction everyone is enthusiastic about.
  
• “Working with me” document: how I think about collaboration and how to be a good partner (in both directions). Don’t get too fussy/make expectations too high on this, though. Here’s Stripe COO, Claire Hughes Johnson’s.
• (externally-facing) Personal website: someone once told me this made them want to be my friend, which I found to be high praise! Showing my personality has gotten me a lot of business, and almost all from people that I like!