From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson 

 Thank you so much for joining us. I'm excited for the conversation.

 there's so many different places that we could jump off and, and ideas to explore together. I thought maybe one place to begin, um, and it's some of the stuff that you've written about and I think thought a lot about, or kind of different parts of culture and rituals across different companies and how they become inputs ultimately to the company's success.

And then kind of one example , is you've written about, and a lot of people have talked about the, the culture of writing and documentation at Stripe where you've spent a number of years. And, and maybe you could start by explaining what that looked like and why you think it was so, impactful to the company.

 Yeah, I think that's a really good question, and it's been a pretty neat evolution, I think, in people's attitudes towards written cultures or cul cultures that focus on, on writing. Um, especially now that we move to a more hybrid model. I think the, the virtues of writing focus cultures have just become more and more clear and more and more true.

Um, so I'm really excited to, to talk about this thing in particular. So the, the thing I'll say that I think made the greatest impact about stripes writing culture is twofold. Um, one is that I think at first blush, people think about the impact of writing as sort of like the artifact it creates for the readers.

And that writing is sort of a benevolent or a generous act where you're spending a bunch of time producing something that's so, so that somebody else can benefit from that. That artifact. Um, but what I learned from being in this culture of writing is that actually there's a ton of intrinsic value to writing too.

Um, when you set out to write something, you actually are sort of crafting the way you, that you think about something. So it's really becomes like a, a, a path towards more rigorous thinking. So I think it just made us better thinkers as an organization and not just better communicators or cross-functional collaborators.

 And was that just emergent from the founders or there was some intentionality behind it?

 Yeah, I think a good amount of this comes from the founders, just like sort of any core cultural staple. And one thing I'll say about this and is that John and Patrick are fantastic writers themselves. So they modeled this behavior a lot and we all got to receive the benefits of it. I think the thing I missed the most about working at Stripe is Patrick's emails.

Um, and just before when we were ramping up to this, we were talking about what a wacky time this is. And I found myself sort of wondering what Patrick's been saying to the company about that. Um, so the, these writings amusing. They, they stuck with me. They stuck with a lot of us. So I think just feeling the virtues of writing helps.

Um, and also that they are prolific readers. Um, they just read a ton so you can trust that if someone writes something, it, they might just read what you have to say.

 When you kind of reverse engineer, let's take Patrick's writing inside the company. and, as you articulated it was really exceptionally good. how would you describe it to someone who hasn't read, maybe a memo he shared with the company or something else like that?

 Yeah, I think George Saunders has a nice little shtick about this, which is good. Writing is just, you just want to read the next sentence, . Um, and I think it just says it's shorthand for, it's compelling, it's interesting. It's full of stuff, you know, the, or full of juicy stuff. There's just a lot to latch onto there and to the point I was making before, like it, it reflects.

real interesting thought. Um, it's not just a piece of writing it, it says something else. Um, and yeah, I was thinking about just in prep preparation for this, how I knew that Stripe was a writing focus culture, sort of what gave me something to chew on when I got started. And I was thinking of my first day and just receiving this how we operate document.

And I'd never received anything like this before at a company I worked and I just like went to my desk and got started. But we got this how to operate our operating principles and it had quotes from Tyler Cohen and it had a story about Richard Fineman and it taught me what a trap door decision was.

I mean, I didn't know anything about these people or these frameworks, but I was totally hooked. I was learning, I was curious about these new characters that sent me down, sort of other rabbit holes. So yeah, I think these qualities of good writing is, it's just, it's just compelling.

 how do you think about, you know, if a friend of yours is working at your company or someone reaches out to you and says, I wanna become a better writer o, other than maybe just reading great things, what would you tell them to do?

 Write a lot. You know the, I think the thing that gets in the way of a lot of people writing is it's so uncomfortable to open up a document and see that cursor blinking at you like that. It's sort of just like an excruciating feeling of like, wow, this blank canvas is, yeah, it's empty and I have to fill it with my ideas, and it creates a, yeah, there's a real high barrier there to just get going.

but all the best writers I know have a habit around it. They will just like get their ass in the chair and write. Um, and I think it's hard to do and if you read a lot, like you said, um, you will also sort of notice the flaws in your own writing. So just spending a lot of time writing, reading, editing, um, there's that, that quote.

I like, I would've written you a shorter letter, but I didn't have the time. It's just kind of getting in there, getting the words on the page and then editing your own stuff.

 Is that how you end up sort of writing? Let's say, you know, you're putting together a, I don't know, a project proposal or something at a company and you start by opening up a blank Google Doc or Notion Doc or whatever. What do you tend to do?

 Oh yeah. I just write and write and write. I very much think through my keyboard. I cannot think about anything clearly until it's written. And I think this made me maybe like a particularly good fit for. Stripes writing culture. But yeah, I, I very much use it as a tool for thought. Um, and usually kind of like the organizing principle around it will reveal itself over time.

It's kind of like sculpting or something. You know, artists say they like see the, they see the sculpture in the block of marble or something. And I think eventually if you have enough words on the page, you find the ones that are the most interesting.

 Can you bring to life, like when, when you use the term Stripe had like a very strong writing culture, maybe what that looked like on a daily, weekly, or monthly basis. And maybe how you might contrast that with maybe a quote, normal company or a company that maybe doesn't have this level of, um, intentionality around writing.

 Yeah. Yeah. So, . I think the shocking part about stripes writing culture is just how much internal documentation, and I don't mean like, here's how to use this thing. I mean like, here are my thoughts on how this thing goes. Like just how much of that exists. Um, patio 11, you know, longtime Stripe and sort of startup whisperer, he says, he called the reading the Library of internal documentation, one of his favorite job perks,

So what it looked like tactically, and I wish I had saved screenshots of this or something because it was truly wild, but we did most of this in email. Um, and again, I should say that this is, Stripe is probably very different today then it was when I left it. But the, the way that it looked to me at this, at, at the time I was working there is a bunch of Google groups and these might have names like PJ notes as in Patrick and John notes or retrospectives or a state of or org changes or announcements or new hires.

and those were all on the left hand sidebar. Um, and they bolded up if they're, if someone wrote something new to that thread. So I could click into the retrospectives Google group and anyone at the company who had produced a retrospective about something they had worked on would be in there. So this really led to a ton of cross-functional and like, I mean, like, people in distant parts of the org, I could just read about their musings on something.

I think you would be surprised at the frequency of these kinds of documents. So when I said like, you can click in to see if there's a new retrospective, there was always any retrospective, somebody was always writing up their learnings about something they had shipped. These were very high frequency mechanisms, and I probably should have said this earlier when we were talking about the virtues of writing.

Um, is that at Stripe, the practitioner set the record for the company. It wasn't just managers reporting on what their teams were up to. It was the ICS who were doing the work, doing these really fantastic write-ups of what was actually going on. Um, and it's completely democratic. Anyone can publish to any of these listservs and they did it often because you kind of got org points for doing this stuff.

Um, and the better your doc, probably the more people who read it. So yeah, the frequency was very high.

 And it was, it's sort of related to any, any part of the business.

 Yeah, exactly. Um, I think one way to think about this is paper trails versus a curation where a paper trail might be just like, Hey, these are notes from the meeting or, um, these are the actions that came out of this thread. And a curation is just, okay, I've like done this body of work and now I'm gonna talk about it in a way that's more interest that a cross-functional person who doesn't really have context on the details of this work stream might find interesting.

So one example I like to, to give, so I published into the company a state email when I was working on straight press and state emails have this quality of like, here's the state of the, here's the state of the project. So I had published one of these into the company and there was a section at the bottom with kind of questions I was struggling with.

And the particular question that was on my mind was, how should stripe press pay its authors? The traditional advance on royalties model didn't seem like quite the right. Fit for what we were up to, but I was kind of stuck on what was, so I just published this into the company open question, and an engineer I had never met in an office across the country had previously worked at a record label.

And he had, he shared the model that they used to pay their artists at the record label, and that one was a lot closer to the one that we ended up working with. So is this kind of like, I would've never found that person without writing this email, but because I had sent this sort of tuning for up to the company, he was able to find me.

Um, and it just created like a very authentic, organic way to collaborate. You know, this didn't show up in anybody's perf, um, he probably didn't report that he was doing this up in his weekly snippets or updates. It was just a true collaborative teammates helping each other moment.

 That's really helpful. And so you mentioned sort of state emails, uh, uh or documents, retrospective emails or documents. Could you walk through maybe 3, 5, 7 of like the, the formats or things that tended to repeat themselves or the templates that were used in some level of frequency?

 Yeah, I think probably the templates would be sort of like, not best described, but maybe like distributed after something. But I think even just the insight to have a template is pretty helpful. Um, the, the main canonical list that Stripe was shipped at, so just what did you ship lately and shipped? Could encompass something that was user facing or internal to the company.

In fact, over time it was became shipped, un shipped. It was also things that you had kind of like removed from the system, um, as a way to prioritize the infrastructure work that the company was doing. And yeah, I think just the insight to have templates for these sorts of things to help guide the hand in writing this stuff.

Um, I think that's actually the most important thing. Every company needs to know a different thing, um, or wants a different set of. Information to be reflected in these emails. So I don't know if the content is as interesting as just the idea to guide the hand in the content in the first place

 So like with the shipped email, what would be like the format of that, or what's the format of a retrospective email or document?

 at Stripe. These were just pros. Um, but I've worked with companies to help them build these templates and they look, they truly do look different at every single one. But here I have one that I give out to companies that I work with. So I'll reflect what ended up in the template for a shipped email if I was working with a company.

So it was the, a summary of what happened, what did you do, how does it help the company? What shipped, what exists now that didn't before? Context and motivation. Why did the company wanna do this work? Why was it prioritized? What other works at the stage? What should be different now? under the hood. The story of how it got here for our eyes only.

Um, so what could, what would go down in the history books about it? Success criteria. How did we know if we did a good job? What were our metrics? What was experimental design? What's next? How does this impact our future? How to keep tabs, if anyone wants to stay up to date on what's going on, where should they look?

Asks if there are any for the readers or onlookers. And then thank you. So the people who contributed.

 What about for. and that was really helpful to kind of bring it to life. What about for when a a, a project or work stream is getting kicked off? What, what's sort of the written collateral or formats that you've noticed are are useful when you're getting something going?

 Yeah. I'm glad you brought off kickoffs because I actually think this is sort of overlooked in companies today. Um, things often don't seem very interesting when they're first getting started. But in fact, one, they are, and two, somebody might have an insight that could help you do a better job. And three, and I see this all the time, even for companies that are super tiny, which is excruciating to me, which is that two groups are working on the same thing.

So anyway, I think just the kickoff in general is pretty, pretty overlooked. But I do have another template for this, So kickoff template and again, this is like the one that I would deliver, um, to, to clients when I was working on Kool-Aid factory. So what is your experimental hypothesis? So what's the overview? What's the issue you're trying to solve? What questions are you trying to answer? , what is your hypothesis?

Um, and how, why did you come to it? What's the baseline information? This is based on other potential outcomes. So what, what could happen in the experiment? What would that teach you? Non goals, what do you think is out of scope? Prior art, has anything already been done in this domain? What worked or didn't work?

Measuring the impact. What are the immediate and long-term metrics or goals you expect? What are the long-term outcomes you expect? And then maybe some stuff around experimental design. So who variations and controls, who are your targeting, when and where? And then scope around the and the project team.

So your timeline, your budget, your constraints, any blockers, any succession plans. And then things around the project team and communication. So who's the dri? Who's in the core working group? Who are your stakeholders? Who are your sponsors? What communication channels will you use? And if you need, what project principles might you want to keep in mind as you work or make decisions?

 what is being, so involved in written cultures, taught you about the role of context in allowing individuals to do great.

 Yeah, that's a really good question, and I like it 

because it highlights an understanding that you don't always know exactly what inputs or exactly what information you might need in order to do a great job. , you don't always know exactly the right doc to look at. You don't always know exactly the right person to go to, but you do wanna set the conditions.

And I, I sometimes I refer to this as like the primordial ooze or something where it's just like you have just like an ambient feeling of things. Um, you have an ambient sense of how your users talk and like what words they use. And you don't need to go to a doc that's like, here's the lexicon of things that our users like to say.

Um, but just if you listen to them a lot, you'll just get a sense of how they talk about things. So I think this kind of context setting, sort of overall vibe of things, primordial, uzi kind of looser stuff, um, is often the stuff that produces the best ideas and it allows you to make connections across seemingly disparate ideas.

 how does that map to the fact that, you know, even if you're at a relatively small company, call it 50 to a hundred people, there might be more things than you could possibly read or consume in any given day. And you kind of have to pick and choose. And one of the things that I've noticed, and I think it builds on some of the things that you were sharing, is that there's a tremendous amount of value in context that at times seems completely unrelated to someone's job. And when a lot of people think about context, I think they think about it in a given role or function, and they think about it very narrowly. and, there's this tremendous upside that you get when there's this kind of amazing amount of cross-pollinization and there's context that seemingly is unrelated to someone's job that ultimately allows them to do a better job.

And you, you could come up with a zillion examples, but it might be a product manager that, has access and understands what the, what the actual p and l of the business is. And like, well, this person's just doing this feature over here. It doesn't matter, but, but there's this magical thing that happens when someone is exposed to this context, maybe in some other pocket of the business. I think the, the challenge is that, from a, how do you disseminate information? How does someone even choose what to consume? Given that certainly when you get into the hundreds of people, there's probably not even enough hours in the day if you wanted to spend all of your time trying to consume this stuff.

So do you have any thoughts on like, how does stuff get organized or, or how does stuff get routed other than maybe just letting the end user decide whatever they want?

 One is that like this information overload, It's a total thing. It's a total experience that a lot of employees have, a lot of leaders have, and I think just humans are like pretty good at this. You're pretty good at figuring out what's interesting to you over time.

 Um, and where I think the company sort of architecture comes into play here is what, what slack channels do you have? Um, is there a retrospectives one, if not the retrospectives will probably get stuck within team channels. So if you're the company leader and you wanna see all the retrospectives, you'd have to follow every single team and keep kind of checking and scrolling to make sure there's nothing interesting in each of these channels.

But if you pull this out and have the retrospectives channel, folks can cross post or it kind of sets the stage for more of this kind of thinking, especially being like this master architect role of this slack channels and communication norms can help a lot with this. Um, and one counterintuitive thing that I've encountered with, with the companies I work with through Kool-Aid is the intuitive antidote to information overload is to just distill, have fewer channels. But actually I advocate for having a lot more channels, um, that way they can stay more narrowly focused and folks can kind of set their permissions accordingly. Um, I will say this takes a ton of work and gardening and it's really hard to be effective at it, and it's really hard to evolve this stuff in the right ways.

And this is where I think the templates you were talking about help too. Um, but it's a hard problem. Um, it's a hard problem, but it's, it's one worth solving and we're thinking a lot about because like you said, the, the working with the right context and the right insight and the right cross-company ideas and global optimization like that is the recipe for the best work.

So figuring out a way to, to incentivize it or to make it easier for folks to do that is super important.

 Are there some examples of the way that you've set up Slack with either clients of yours or at your own company or at at Stripe that maybe is tangible that obviously I think the answer to like what is the ideal architecture that you're getting at is, it depends. Depends on so many different things. But like are there examples of. Most companies would benefit from configuring Slack or notion or something in this way, or experimenting with this channel or organizing in this way that might be useful for others.

 So I think the set of channels or spaces that's often overlooked in this master architect's design is the ones about this curation layer that we talked about, the retrospectives, the state emails, the shipped emails, um, It's, it's obvious to organize the communication channels around working groups.

 It's less obvious to, to set them up around these curation layers. So a few channels that I like to advocate for in terms of the curation layers are org or team updates. So this is the one for people updates about like the shape of the organization, where people sit in it, if new people are being added.

Um, and I'll, I'll just like add an annotation on this one, that nothing makes you feel more out of the loop at your company than somebody showing up next to you and like, is your boss or like a collaborator and you didn't even know that they were coming. Um, so this one's super important. Starting line is another one we already talked about kickoffs, leader snippets.

I really like this one. Just like what are the company's leaders up to? Um, and this one's super important cuz if you're working on stuff that's not showing up on any leader's radar at all. There's a good question to ask yourself there Shipped. We talked about what new stuff just launched state of, we talked about how are things going with existing work streams.

Um, some companies can end up having sort of like a neophilia where they're obsessed with new things, but they don't revisit old things ever. So having a state of and retrospectives that would put in this category two notes and decisions, places for people to scan about relevant meetings or insights.

And I do think there's a positive feedback loop here where asking yourself like, Hey, what, what parts of my work might my cross-functional counterparts be interested in kind of reinforces this, like global thinking and helping each other out. Um, job openings super easy. Recruiting is hard to see what new roles are opening.

Um, and kind of a silly one, but board slide review. I really like, um, when companies do this well, they'll, they'll share and sometimes there's a, a redacted version of it, which is totally fine, but just sharing what you share with the board. To this point of just like help let helping people level up, help them understand what the company's talking about with the raw artifacts.

Not like some summary in all hands, but like the raw actual thing you're gonna present. I guess this kind of brings us into an interesting topic and, and sort of really relevant to some of the consulting work that you've done. But, you know, if you're a 30 or 50 person company and you're listing or have read some of your ideas and, and you want to shift your company in the direction that you're describing, where do you begin or how do you get started and how do you think about kind of the steps to get from here to there?

Yeah, I do think there's a pretty clear formula for this, so I hope you will try it and tell me how it works for you and what doesn't if, if you're blocked on anything. But my sense on this is if you build the channel, they will come and post. So if company leader says, Hey, we are now opening up this retrospectives channel, I want our company to be more reflective about how things are going.

Here is the place to post your work. And just creating that channel, create that space for people to post. Um, then be super prescriptive about how to lean on them. So what kind of work do you want retrospectives on? what's the template for that? How often do you want people to post? And then these two critical components that are really easy to overlook but I think are super important is when you launch that channel, seat it with really good content.

So before you open up that channel, tap a few people around the org with work streams that you think deserve retrospectives, help them produce really good examples for the rest of the org. And as soon as you open that channel, have these folks post that way, there's, you don't get this empty shelf problem where you open the channel and there's nothing there, or it's crickets for a while.

Um, and you're modeling good behavior right off the bat. Um, and then, you know, whoop up those posts. As the company leader, if you are paying attention to something, other people at the company are realizing, Hey, this is a way to get leader eyes on this thing. Um, so they will do that too. And then the next overlooked tactic is to appoint, I like calling these like rangers, channel rangers, who's in charge of upholding the standards.

Um, so going around to the company and being like, Hey, this might be a good candidate for a retrospective. or when something is posted, being able to sort of edit or share feedback about like what's working and what's not. Or even being a person that people come to before posting to make sure that the quality is up to snuff.

 Would, would you start with like a single artifact and a single sort of document and, and channel and make that successful and then add another one and another one, or, or what's the path into if kind of the end state is the way that Stripe operates and you know, the starting state is like, there's not that much writing and documentation going on in our company.

Like what's the path to get from one point to the other?

 Yeah. I, I think actually just like, kind of like you would at product, just get a few people using it. Um, so I would start with the place of what do I wanna hear more about? So I keep using retrospectives because I know that companies like sort of, um, , yeah. Becoming more reflective about their own systems and processes.

And that's a great way to kind of learn from yourself and what's going on. But there's other places to start. Like, uh, two teams are working on the same thing and we don't notice all the time. Let's start a kickoff's channel. Um, and then just getting a few people to write for those. And again, as company leader, you're in a, a privileged position to be able to ask for work whenever you want it, in whatever kind of way that you want it in.

So setting up those templates personally, asking people to post to these channels and then just getting it going. Um, not everything will stick. Um, but the stuff that does can make a really big impact.

 how does this sort of, this set of ideas map to who you hire and do you think getting good at this is something that's incredibly learnable or you kind of think about hiring people and you evaluate them based in this case, how excellent their writing.

 Yeah. Yeah. I, I believe anyone can get good at anything. I really do. Um, I think we've all heard the stories about companies like WordPress. I think they even interview completely asynchronously. Like they'll hire someone without even a single, even a single synchronous meeting. And we should do a fact check on that.

But I, I think that's true. Um, but I think people can get good at writing, especially if they're in a culture of writing where there's a bunch of good writing to be read. Um, and then another mechanism that I like and I help companies with sometimes myself, is to just do this thing we call red penning. So if you've got writing, just bring it to a few folks and they'll help you edit.

And it's pretty easy to just spot or appoint your, your great writers to this role. And you can make a big stink about it to the company. Like, Hey, these are the company's red pens. Like, you sort of might do a security review or a launch review or something. You can also do a writing review for internal or external docs.

So I like, I like having this group of red pens. I think I worked with one company who they, uh, they had everyone who was the red pen put the pencil emoji in their, in their slack name. So everyone knew who they were.

 how does the writing express itself in what you think good interview processes look like?

 you can tell a lot just by the way people email. That's a first step. Um, and yeah, it could be interesting to see someone write up a memo on something and I'll say, that doesn't even have to be about a work related thing. It could be about anything. Um, oftentimes that the best writing comes from, um, there's a workshop I actually do with companies called Writing and I Care a lot, memo, and we walk through the writing process to just write about something you care about.

Oftentimes this comes from like, something someone's persnickety about or an opportunity, they notice it at work and then we just draft the memo on that. So anyway, I love, I love starting with just like a thing you care a lot about, um, inside or outside of work and trying to hit some pros with that. Cuz good writing comes from feeling.

 One of the thing I've, I've been long fascinated by is, you know, so, so many of the different things we do at First Round involve helping kind of open source ideas that people have, mainly about different facets of company building.

 And I've, I've found it interesting that like in many cases the more quote senior someone is, the less interesting and practical and useful the things that they communicate at a conference on a panel and how there's often a disconnect between what they're communicating and what in this case, the audience wants to know.

 And, and part of it I think is that the more senior you get, You want to, you feel like you should be communicating big, interesting, visionary type things. And for example, you know, going to a conference or something and explaining the way you run your Monday morning staff meeting feels like very beneath you. And so you need to say something smart and brilliant. And I just, I, I have thought about that a lot.

 Yeah. I mean, one, one thought about this sort of, this, I have a lot of thoughts about this, this, yeah. This. Why, why are, why are conference talks? Why are they so boring or something? Um, and I like your ideas around this, or, yeah. Why someone who's big and important might wanna share a big important idea or something.

And one principle of writing that I try to stress in these workshops that I offer is, That the, the summary is often pretty boring because it's obvious. And the more interesting piece is the edge. But it's tempting to start with the summary because, It seems like the most helpful place to start, but actually the most interesting thing is the, the piece on the edge.

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Former Stripe and Figma leader and founder of The Kool-Aid Factory Brie Wolfson takes us behind the scenes at how company cultures evolve over time, from operating principles to documentation and rituals.