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

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

Brie Wolfson: Thank you for having me.

Brett Berson: 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.

Brie Wolfson: 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.

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

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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.

Brett Berson: 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.

Brie Wolfson: 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.

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

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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

Brett Berson: 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?

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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.

Brie Wolfson: 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.

Brett Berson: 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.

Brie Wolfson: 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.

Brett Berson: 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.

Brie Wolfson: 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.

Brett Berson: 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?

Brie Wolfson: 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.

Brett Berson: 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.

Brie Wolfson: 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.

Brett Berson: That's cool.

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

Brie Wolfson: 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.

Brett Berson: 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.

Brie Wolfson: Yeah.

Brett Berson: 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.

Brie Wolfson: 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.

So it was like, how quickly can you get to the edge idea? Um, that's one thought. Another thought I had when talking to an expert on something recently about how they communicate to beginners is they feel far away from the beginner and they don't know h how to think about how much the beginner knows. So maybe one example of this is, I feel like when I see a child, I have no idea if they're like four years old or 10 years old.

I, they're just, they kind of, I don't see enough children to know the difference or something. And maybe experts are like this in how they relate to beginners. It's hard to tell what a beginner would know. So and so you kind of talk down to people by accident, um, or state things that you don't know are obvious to them too.

Brett Berson: And so then I guess it comes down to sort of the age old idea of knowing your audience.

Brie Wolfson: Yeah, I think so. I think so. Or just having confidence that they will get it. You know, Stripe had a principle around this. We called it talking up instead of talking down, like, assume people will get the complicated concepts. If they don't know a word, they'll just look it up. It's not a big deal. We all know how to use a search.

So just having confidence that your, your audience can sort of rise, rise to the occasion of your big, complicated ideas. And maybe the last part of this is, is there's this essay I love, I think it's called Re Reality, has a surprising amount of detail

Brett Berson: It's the best. It's,

Brie Wolfson: Yeah. It's so good.

Brett Berson: dozens of people. A friend of

mine shared it with me many years ago.

Brie Wolfson: yeah, it's so good.

Um, because it reflects this thing that, you know, when you're deep on anything, which is, there's so much there, there's so much happening. Um, and at strike, we talked about this in terms of kind of turpentine, sort of what's going on at the one inch level. And this comes from a quote, when artists, when critics get together, talk about art, they talk about line and form.

And when artists get together to talk about art, they talk about, yeah, where to buy cheap turpentine. And we really aspire to talk turpentine, you know, talk about things like that are going down at the low level, not like the high level summary that's boring , but like, what's actually going on here? Um, and maybe that's the part that's like the surprising amount of detail.

Like that's what makes something content good or that's what would make a talk good. It like surprises you, you learn something. Like to go back to the, the Stripe operating principles like. Telling me a story about Richard Fineman starting at the lab. I'm like, who is Richard Fineman? Like, what is his lab?

You know, I, it was kind of weird not to know it. So then I just found out the answers or like, who's this Tyler Cohen guy? Um, all these things were sort of new. I learned something through reading and maybe just getting to the surprising amount of detail parts first is like the right way to go.

Brett Berson: when you talk about this, it, it also makes me think of the, um, we often talk about in, in the, um, in the context of founder. There are some founders, and I think this exists for, for basically every role that are simplifiers and there's some founders who are complex classifiers. Um,

Brie Wolfson: the complexifies, does that ever work?

Brett Berson: very rarely.

and and I, and I've, and I kind of wonder why people behave in that way.

I think kind of one take would be like the classic idea that if you can't simplify, you don't truly understand the thing.

Brie Wolfson: Yeah.

Brett Berson: Um, but I also find, and there's obviously gradation of this, but it's amazing kind of this dividing line and in so many cases it actually doesn't have to do with how complicated or technical the

Brie Wolfson: Mm-hmm. . Mm-hmm.

Brett Berson: Um, and you know, there's a meaningful portion of meetings that we go. you know, somebody's building, pick any topic and you leave in a lot of cases more confused than when you went in. And it's also disconnected with like how long the person has been working in the space. So, and, and there are people that would be considered expert. I think that you still leave and you're more confused. I dunno. Anything come to mind when you think about that?

Brie Wolfson: Oh yeah. Yeah. A lot comes to mind. Um, maybe the first thing is this talking up thing where it could kind of be a status game to be like, I know so much about this thing. Someone like you would never understand it cuz I'm so deep and I know everything about it and I can articulate all the crannies and all the complexities.

And someone like you, who's not an expert like me, would never understand. So there's kind of a status game associated with confusing someone or something. I, that, that part is resonant to me and I've, I've encountered this a bunch and I always just wanna say, well, try me explain something hard.

Maybe I'll get it, maybe I won't, I don't know. Um, . But I, yeah, I, I feel this on the other side of things, it's like a curious person that likes to encounter experts. I feel I'm in over my head a lot, but the very best teachers, the very best communicators. Yeah. They're simplifiers. They make them intelligible, they make ideas intelligible to anyone.

Um, yeah. Richard Fineman an expert at this for sure. Um, yeah, I'm thinking of this story of Steve Jobs. Apparently he had this, uh, this neon sign outside of his office that was quoting, I forget who, but it, the quote is, simplify, simplify, simplify. And he had the first two simplifies crossed out . Yeah. I just love that.

Even the most simple idea can be simplified.

Brett Berson: If someone is a complexifies, what do you think they should do if they want to get out of that space?

Brie Wolfson: More time. More time. Distilling a lot more time. Yeah. This is a probably more apt place for the quote. I would've written you a shorter letter, but I didn't have the time. It's really hard to distill ideas. It's really hard and it's really worth it. It's really worth the time. And often I think the complexity in communicating Yeah.

Reflects the complexity and thinking. So there's probably, you'll probably learn by spending time with it. And then the second piece is feedback. Gosh, I sometimes I'm like, I have no idea what that person was talking about. And then they'll just Walt away, like, we had a great conversation or something. And yeah, I think sticking with the ears that you wanna fall on and ask if you were understood.

Um, people who I think are great communicators will often ask, um, You to like play that back to them or something to make sure that you're on the same page. But yeah, it's hard.

Brett Berson: When you think about the process of, of like distilling something down to a new framework or something that is memorable, do you think that's also kind of just a function of, of editing and workshopping, or maybe some people are better than others? I, I'm always intrigued by sort of people that come along and.

They kind of wrap an idea in a very specific way that that sticks in people's brains.

Brie Wolfson: Yeah.

Brett Berson: So like, um, a super simple sort of example that comes to mind is that Kim Scott came up with the sort of language radical candor and sort of has this x y plane. And in a lot of ways it's an idea that that's intuitive to a lot of people, but it caught people's imagination in a certain way.

I think when, when we published the original article, you know, before she wrote the book, I don't know, something like millions of people read it.

Um, and, and I, I'm, I always fall in love with sort of that type of stuff. Um, and so much of the things that I find. That have like these step functions in the way that I think about things are packaged in that way.

The, the, the essay reality is a surprising amount of detail is, is a really good example of that for me. And you think some people are just better than that or at others, or, or, or, the ritual of distilling kind of increases the chances that you kind of can take something and package it in a way that that sticks in people's brains.

Brie Wolfson: Yeah, I, I think the latter is true. I think the, the best way is to sort of just like keep honing and keep the chisel out and hitting it. And the other best way is just to play things off people and see what they say back to you. You know, the famous story of Stripes mission statement, which is increase the GDP of the internet, is that the company didn't come up with it.

I think of some reporter said it and it was like, oh, okay. That's what you heard. Cool. Um, and now that I'm building this company on my own and I'm trying to understand how other people see the product, I'm always listening for cool language about how they describe me. Um, when someone asks like, what does consulate do?

I will turn to anybody next to me and say, what does it do? Cuz I wanna hear how they talk about it. Um, it's so convoluted in my head sometimes, or I, I don't know if the things I'm saying is landing. Actually just hearing how things bounce off others is probably the most effective way to see what worms will stick in other people's ears.

 So, yeah, I think you gotta play in the idea maze a little bit.

Brie Wolfson: I think you gotta bounce things off others and just get a sense of what sticks, what sounds cool to you, what others report they think sounds cool. Um, it's a process.

Brett Berson: So let's go in a little bit of a different direction, kind of building on some of the conversations about Stripe. I guess, what do you think are interesting parts of the culture that maybe don't get the same amount of attention or that you kind of studied, didn't feel like some of the inputs to the success of the business?

Uh, maybe outside of, of, of writing and, and documentation.

Brie Wolfson: Yeah. Yeah. The, the. the first one I'll say, and maybe this seems obvious or a little meta or something, but it's just the focus on culture, the intention behind it, the idea that culture is a real thing and you can talk about it with real words and you can bend it in a direction, um, was like a huge unlock for me and I think really helpful for the company.

Um, a lot of teams or companies treat culture as a sort of like ethereal thing, but just the very idea that you could grasp it and talk about it was helpful. So writing down the operating principles, talking about the culture as a thing, um, that was like a huge insight and I think helped a lot. And the, the second piece of that is of the intentionality is actually doing something about the culture.

the culture was expressed in every single corner of the organization. This like polish and meticulousness and leveling up. And the best example I could think of for this is that at some point in the company's history, the, instead of like music playing in the bathrooms, it was language learning tapes.

And it's just, it's kind of funny to think about, like, I don't think anyone's gonna learn a language in there however many minutes a day in the bathroom. But just the idea that the sound in the bathroom is like a corner of the org to express yourself in is just, there's a lot, there's a lot there. Um, and I think some people can find this exhausting, but I think it said a lot about just how kind of meticulous and corners focused the company would be and how far of a length they would go to be intentional about things.

Um, Yeah. Any reactions to that? I'm curious if you think, that sounds like ridiculous to spend any time thinking about the music in the bathroom.

Brett Berson: I think that peculiar stories have just extraordinary impacts on culture, like right the way that we behave, the way we accomplish work together. who gets hired and who gets fired, and maybe that's kind of an example of something that seems trivial, but can live as a story that reinforces a specific set of behaviors

Brie Wolfson: Yeah, I think so. And maybe this relates to what you were saying about like how do ideas carry as they're, they become memes. people like to talk about them as part of the mythology and yeah. That, that resonates. It gives you something to talk about.

Brett Berson: and then that, that is one of the most effective ways to get people to behave in that way and effectively kind of live the value.

Sort of on the theme of, of articulating culture, operating principles, what advice do you have for, for companies that are trying to do this, maybe that would be fresh or, or maybe folks haven't heard as they're thinking about the process of codifying how to behave.

Brie Wolfson: Yeah. Yeah. It, I think there's a really strong relationship between language and behavior and we've been talking all about just, yeah. How do ideas proliferate or prom. Um, and kind of setting up the language is a great way, and operating principles are like the company's best chance to make this happen, um, is to create a set of language that helps guide behavior.

Um, the coolest thing about operating principles is they, they, they're meant to cross power lines. Anyone should be able to say it to anybody else, um, as a, as a way to correct behavior. And I think the thing I see a lot of companies tripping up on is they don't make these things fun or interesting to say.

Um, so actually focusing on like, what's the Mimi version of this? not do hard things but move fast and break things is way more fun and interesting. Um, so like, what's the Mimi way to say this thing? Or what's the US way to say this thing? Um, Stripe had one that was front page test, which is about, i, it comes from more in Buffet.

You know, if, if we did something, could it end up on the front page of the New York Times? There's, that's more interesting to say than be high integrity or something. So, yeah, I think thinking about the Mimi version of the, of the phrase and what language people might use in the run of work,

Brett Berson: When you use the term operating principles, is it interchangeable with the idea or, or, or word values, or you think about those two things differently in some way?

Brie Wolfson: I prefer the term operating principles. And my, my rant on this is that I think values feel very kind of core essence. They, um, they're meant to sort of be static and stable and a foundational belief, whereas operating principles are meant to evolve. And the whole point of these companies is that they are evolving and growing.

Um, the ones that, that we work in at least, and having principles that can change as the need needs of the company and the business and the team changes is super important. So move fast and break things is a great example. Made a lot of sense for Facebook or for meta in the early days. Didn't make as much sense in the later days.

And I think they actually changed it to move fast with stable infrastructure or something. Um, but operating principles, it gives the, it, it gives permission for them to change.

Brett Berson: I, I often wonder, you know, some of these Mimi things or the weird ways that companies operate. how do you disentangle if they enabled the, the company to be successful or the company was successful in spite of those things?

Brie Wolfson: Yeah. Yeah.

Brett Berson: I also think about that like in the continuum, how the company grows because what you tend to see is a lot of the weirdness in the early days goes away at scale.

So like the classic example would be, well, we have no managers. And Google was famous for this, right? They had, you know, an ang manager that would have a hundred direct reports, for example.

Brie Wolfson: Mm-hmm.

Brett Berson: And then the company grows and grows and, you kind of converge on these, you know, models that have probably been around since Drucker before.

Um, and it, and, and then you start to say, okay, well take the Google example. Or maybe Stripe was famous for no product managers for a very long time, I think.

Um, and then you're like, maybe Google was successful in spite of having a hundred engineers report to an engineer, but, but because it also is very Mimi, then you see a bunch of other companies sort of adopt that thing that may have actually inhibited the company from being successful.

Brie Wolfson: yeah. Yeah. Well, I do think there's such a thing as culture market fit or something. Where the company or the culture sort of has to match what the needs of the business are like. Stripes culture of meticulousness was appropriate for a financial infrastructure company. We have to get everything right to the hundredth decimal place.

Um, and if we're gonna do that in the product, we might as well do that on the blog too, so that the whole company has the whole habit of that. Sigma didn't have as much of this culture cuz it made sense for Figma because it was all about work in progress and opening up your files and showing the mess.

So a culture of meticulousness in some ways was sort of less relevant or less true. So I don't think culture is always best imported from, from place to place. Um, and I do think these stories can be pretty powerful. But to take it back to the writing stuff again, any great writer knows you gotta kill your darlings.

The stuff that works one day might not work the next. And being willing to get rid of those mechanisms is, is hard but important. Um, companies aren't often very good at that, but. The self-reflective ones are, yeah, I'm laughing. My coach, my soccer coach would always say this, are you, are we good in spite of this or because of it?

And I think it's a good question to ask.

 taking a little bit of a turn when you zoom out. How would you compare the cultures of Stripe and Figma? You know, both are really wonderful businesses that have been created called in the last decade that you got to study relatively closely. in what ways would you say they're quite similar and in what ways would you say they're like, diametrically opposed, or quite

Brie Wolfson: Yeah. Yeah. This is actually what got the whole Kool-Aid factory project. Started, which is that wow, there's so many ways to build an amazing company. Like there's just so many different ways to do it. And a little bit of that is, has to do with the leaders and a little bit of that has to do with the product and the team and all this other stuff, but a lot can work.

So what do I think the companies had in common

that would be non-obvious? Maybe it's just like people that really cared a lot, just really cared. Um, just wanted to do a great job or just obsessed with making it work. 

yeah, that was a quality of both places at, at both Sigma and Stripe. If you were to just sit at the lunchroom with anyone, you would just go on and on and on about what's going on at the at work. Which is awesome. People are really deep on stuff. They really felt it. And what was different?

Figma was very silly. It was zany and wacky and colorful and bold. And stripe is pretty earnest, serious. And again, I think this has a lot to do with the kinds of products they're building, but that part felt really different. Um, yeah. And virtues both, both have their own virtues.

one thing you said that's super interesting is this idea of, you know, there's just a bunch of people at the company that care a lot, what. What does a company do in the early days, in the dozens and the first few hundred employees to create like a lot of care density?

Brie Wolfson: Maybe there's something around, and I don't wanna focus, writing is not the only way to express oneself in this, but maybe it's just a creating places for people to do that sort of deep dive flavor of work. Um, you know, I've noticed a lot of companies. away from the all hand style presentation and more towards like the demo and tech talky thing.

And maybe this has to do with that where it's just, Hey, come and show us what you do. Like what are you getting into right now? And making that exciting and visible. And, uh, a way to get org points is just like show when you're deep on something. If you can talk for 20 minutes about something nonstop, I think you probably care a lot about it. So the company's saying, Hey, come and talk about this thing for 20 minutes, nonstop. Or like, host a luncheon, learn on this, do a tech talk on it, write a doc, and we're all gonna, I'm gonna reforward it to the company as the company leader and be like, this is an example of amazing stuff.

Maybe it's just allowing space for the details and the weird corners and crannies of the work. Um, whereas like we were saying before, a lot of sort of the cross-functional stuff often, or like the high level stuff often goes to the summary place, the high level place, the not too much detail place, but instead allowing people in the corners of the organizations room, on the company stage for the really deep stuff.

Um, and, and maybe this is where the talking up comes too, is like, it's okay if not everyone will understand the math that went into it or not everyone will know all the technical terms, but just like wax and wax and wax and go on about it. Um, and we're gonna listen.

Brett Berson: I guess it kind of makes me think about the role of narrative and rituals inside of a company relative to the people that you attract and hire and like, how do those two things fit together? One thing that, that I've been thinking a lot about is like our, our missions in, in, in, in Tyler Parlin overrated or underrated Like I think care's a really interesting topic and most people don't really explore it.

But if you just, I just think if you have a bunch of people that care more about the thing that you're doing or the company or the customer or whatever, the upside there is kind of unbelievable. And I wonder if people, maybe if you look at the first 250 people that stripe a lot of people, yeah, they like the idea of increasing GDP at the internet, but maybe there's all sorts of other stuff going on that got them to care that they could be

selling, you know, all sorts of stuff. 

Brie Wolfson: I think in under, kind of disgusting about Stripe is how do you get people to care about payments, especially a bunch of smart people? And Patrick has a good shtick about this, I think, uh, maybe Keith oi interviewing him. Um, and he says that they didn't look for people with passion about payments out of the gates, because who comes out the womb caring about payments this much?

But instead was sort of drawn to a hard technical problem. Um, and, and Patrick Success talks about sort of falling in love with payments over time for this reason, but he didn't come to it interested in payments, like he backed into it through another way. And like working for a company that has a compelling mission statement, that's a good way to recruit, but it's easy to forget about the mission statement when you're just clickety clocking on your laptop.

You know, it doesn't, it's not always at the forefront. So I don't know if passionate about this specific mission is the vector, but yeah, I think this, like this capacity to care, there's something there. And I also have a sense, or in my experience with folks, people who caring is contagious. If they care about things in one area of their life, they're like, they're prone to caring about things in others.

So people who, yeah, I guess it's described as like a twinkle in the eye or something. Someone can get it one place, they can probably get it somewhere else. So maybe that's a good way in, just like what do you care a whole heap about?

Brett Berson: the caring is, I, I strongly agree with the caring is contagious and lack of caring is contagious.

and a lovely place to end. Thanks so much for joining us in this, uh, kind

of, uh, sprawling and wandering conversation. Hopefully there were some. Little tidbits that might be useful to others, but this was really fun.

Brie Wolfson: Thank you Brett.