Lenny's Podcast: Product | Career | Growth
00:52:26 · Tara Seshan, Lenny Rachitsky
[00:52:26] S0: For sure, for sure. [00:52:34] S1: Help us know all these things. That's why podcasts like this are also useful. Can't put it all in the product. I'm going to go in a totally different direction. I'm going to talk about writing. I asked Brie Wolfson, who knows you well, what to ask you. Funny enough, she suggested questions for the previous podcast conversation I did with Adam Ward from Cursor. So she said, "Okay, you should ask her about writing/thinking. A Tara brief is iconic." Help us understand just what makes your writing your briefs iconic and any tips that might be helpful for people that are maybe trying to get better at writing and writing documents.
00:53:13 · Tara Seshan
[00:53:13] S0: I really strongly believe that I do two types of writing at work. One is writing as thinking, and the other is writing as reporting. Writing as thinking is me writing a brief about why we should build a certain product or why we should take a certain strategy or why maybe a spicy take. But writing as reporting is things like, oh, I'm summarizing the status of what our team has been up to this week and I'm sending over a report about it, or this is our plan for this particular launch or announcement or something like that. Writing as reporting, I happily automate or I use the models all the time to make that as simple as it can be. But writing as thinking is something I never will automate. I really strongly believe that, at least for me, the act of going through and outlining something, turning it into some level of pros, cutting it and editing it, continuing to iterate on it is one of the most important steps for me to get my ideas in line. I think most people actually will paint with a really broad brush, like, "I will never use the models for writing," or, "I always use the models for writing." And actually to me, both those broad brushes are wrong. I think you should use the models as much as possible for writing as reporting. And in as much as you think with writing, as I really do and I think a lot of people do, you should not use it. You shouldn't replace your thinking with it. But my briefs in the past, because I write so much as a way of thinking, is that I will go into a hole, write a brief for a new idea or a product, spend a ton of time refining that particular idea, shop it around with people and have them attack the ideas in it as much as possible and poke holes, make it stronger, and then take it to the next person and do the same thing. And so at Stripe, this is something I did many, many, many, many times over, whether that was to kick off a new product area or to suggest a big change in direction or to analyze a problem and suggest a path forward. And Stripe is incredibly oriented as a writing culture. And there are many people, like Jeff Weinstein, who are also very into writing and sharing briefs at Stripe. Stripe is one of the few places where a brief will go viral inside the company. And so writing as thinking there is really prized, and that's where I did the majority of that writing work.
00:55:47 · Tara Seshan
At OpenAI, I think I still write as thinking all the time. But the shareable artifact here is not really a long doc or a proof of work in that way, partially because times have changed and a long doc is not a signal that you thought through something. Because you could easily produce a long doc that indicates that you haven't. Maybe one of the biggest changes I've experienced personally in my day-to-day, which has been a big, maybe jarring change, is I used to think in a document and then do some translation of that into a presentational artifact, and that would be my indication that I thought through a problem and this is what we're going to do and the team moves in that direction. And now I am way more on mocks not docs, or prototypes not docs. And if I have something that people can try and interact with, or even better, I have results where we tried this, we ran an AB, here's the results, this is why I think we should go in this direction, that is a way better communication tool than the doc itself. And so I still write hundreds of docs all the time, but I do it for me and I no longer do it for other people really. That no longer is the best way to talk and communicate. That is probably the biggest change I've experienced personally in this era versus the previous era.
00:57:12 · Lenny Rachitsky, Tara Seshan
[00:57:12] S1: It is so interesting. I really liked your tip of getting tons of feedback on a doc. It sounds obvious, but you can get to an iconic doc/brief by just cheating almost and getting lots of feedback on it as you're iterating it to make it stronger and stronger stronger versus, cool, here it is first time and it's rarely going to be amazing. [00:57:29] S0: I previously had a manager who told me that the right thing to always do is write a doc to 70% completion and then take it to the people that you need buy-in from and get it from 70% to 100%. And that still is a thing that I do all the time. Because very few great people want to interact with a perfectly polished finished idea. A perfectly polished idea, their new ideas just bounce off of it versus something that has more crags and more rough edges that they too can polish with you together. And I think that bringing people into the process that way where a doc is an underlying artifact for that is one of the best ways to collaborate that I found. [00:58:08] S1: How do you think about AI brain rot and starting to over rely on AI that's just a challenge everybody's going to have? Why not use this magic to help look at something and then we start to lose our ability to write, read long documents? Is there anything you do that you are trying to avoid that?
00:58:08 · Lenny Rachitsky, Tara Seshan
[00:58:08] S1: How do you think about AI brain rot and starting to over rely on AI that's just a challenge everybody's going to have? Why not use this magic to help look at something and then we start to lose our ability to write, read long documents? Is there anything you do that you are trying to avoid that? [00:58:28] S0: Yeah, I think this writing as thinking discipline is one of the main pieces that I employ in my day-to-day to make sure I'm not overly atrophying my thinking abilities. I think I will, again, outsource all writing as reporting as much as possible to the model. But writing as thinking I have to do myself. I have this personal belief that, if I'm going to make someone read my document, I have to at least write it first that number of times. Or I think about this in meetings too, that if I'm going to call a meeting with a set of people, I need to have prepped the collective amount of time that people are going to spend in that meeting before the meeting. And so when it comes to keeping my thinking sharp, I do that writing for the document myself first and make sure I've invested the collective amount of time I expect people to read it at least in writing it and producing it. And I don't really rely on the model either for polishing my prose, which I don't think it really does, or especially not in generating the first version. But I do, of course, have the model help me a lot when it's summarization or translation of content from one format to the other all the time.
00:58:28 · Tara Seshan, Lenny Rachitsky
[00:58:28] S0: Yeah, I think this writing as thinking discipline is one of the main pieces that I employ in my day-to-day to make sure I'm not overly atrophying my thinking abilities. I think I will, again, outsource all writing as reporting as much as possible to the model. But writing as thinking I have to do myself. I have this personal belief that, if I'm going to make someone read my document, I have to at least write it first that number of times. Or I think about this in meetings too, that if I'm going to call a meeting with a set of people, I need to have prepped the collective amount of time that people are going to spend in that meeting before the meeting. And so when it comes to keeping my thinking sharp, I do that writing for the document myself first and make sure I've invested the collective amount of time I expect people to read it at least in writing it and producing it. And I don't really rely on the model either for polishing my prose, which I don't think it really does, or especially not in generating the first version. But I do, of course, have the model help me a lot when it's summarization or translation of content from one format to the other all the time. [00:59:42] S1: So what I'm hearing is write the idea, the brief, the plan yourself as a human, write it yourself, don't start with AI, and even don't use it to improve on the writing, just keep that all human. [00:59:56] S0: Yeah. At least for me, I start myself and I end myself. I might use AI in the middle to research specific elements or drop in some data or go pull some data or help me with-