Steering, Not Rowing: Tara Seshan on Building ChatGPT Work for the Era of AI Coworkers

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Overview

Tara Seshan leads product for ChatGPT Work at OpenAI. Host Lenny Rachitsky also introduced her as leading product for Codex. She joined OpenAI after more than six years at Stripe, where she was one of the first five product managers, and after roles at Watershed and as an entrepreneur-in-residence at Sutter Hill Ventures. In this conversation she lays out how she thinks AI products are evolving. She describes a first era of chat, a second era of agents, mostly coding agents so far, and a possible third era of persistent AI coworkers that people steer together. She also discusses what this means for product managers, why she thinks ambition has become the bottleneck, how OpenAI decides what to build ahead of model capabilities, and why she refuses to let AI do the writing she uses for thinking.

30 min read
2:46

"Founders-led" rather than founder-led

Asked what surprised her most after about a year at OpenAI, Seshan said much of it felt familiar. The talent, urgency, and hyperscaling intensity resembled the fast-growing companies she had worked at before. The difference she noticed was structural. Every previous company she had worked for was founder-led. She described OpenAI as "founders-led": nearly everyone acts as a founder within their own area, and top-down direction is, in her words, extremely limited compared with her past employers. She found this energizing, partly because she came from a founding background herself. She also said the distance between an individual and the market is very thin. Unlike at some large companies, where teams can feel insulated from user demand, at OpenAI each team does whatever it takes to find product-market fit for its own product.

The second surprise went against her expectations. She had assumed there would be a "treasure trove" of secret OpenAI strategy, something like the internal "payments bible" she might find at a payments company. Instead, she said, "OpenAI is open." Nearly every idea about how the world should look, how products should be built, or how models should behave quickly becomes part of the public product or public messaging. When Lenny joked about a secret room with an AGI and a master plan, she replied that she is "at least not in that room." What inspires her, she said, is that the cycle from internal thinking to something users can touch is faster at OpenAI than anywhere she has seen.

6:45

From theoretical to empirical product work

Lenny asked what a longtime PM loses in this new environment. Seshan contrasted it with slower, more established markets. She used payments as an example of a dynamic but established market. There, she argued, you can do "grand strategy" work: reason rigorously from first principles, anticipate a competitor's likely bet, and map out next moves. In such markets, she said, rigor is mandatory. Winners out-think everyone else, and a lack of rigor looks like carelessness, because many outcomes could have been predicted.

In AI, she said, what will emerge is very hard to predict. The market is emergent and fast-changing, and above all it has to stay closely tied to research. So being prolific and empirical matters much more than being academic or theoretical. She described many of her past companies as academic, theoretical places. At OpenAI, instead of writing something like "a PhD thesis" on the plan for the coming period, the question became how to get to something testable with users as fast as possible. She admitted the switch felt jarring. At first she worried she wasn't doing her due diligence or being thoughtful enough.

The thinking hasn't disappeared, in her view. It has become more concentrated. The key step is defining the core hypothesis as sharply as possible. She cited what she attributed to Shishir Mehrotra as the "eigenquestion": the single most important thing to test. Any other grand strategy you invent, she said, is not relevant.

9:05

What hasn't changed about the PM job

Seshan argued that the core of product management has always been the same loop. You identify the question that will decide whether your product works, figure out how to test it, read the results, and feed them back into a sharper hypothesis. Building that hypothesis means combining an understanding of users, the market, and the technology. She said this loop has become the most important capability in the company, and that engineering managers, engineers, data scientists, and designers all now work this way. For PMs, she said, this is good news. Many of the job's "trappings," such as managing execution timelines and producing documents and presentations, have fallen away, and the part that remains is the part PMs have always cared most about.

10:53

From rowing to steering

Lenny raised "loops," the idea of telling an AI what success looks like and letting it iterate until it gets there. He asked whether that pattern would spread from software engineering to all knowledge work. Seshan answered with her central metaphor: work will increasingly look like steering rather than rowing. Agents will do more of the rowing, and people will point the ship in the right direction. She expects the level of steering to keep rising. It started at the level of accepting a line of code with Tab, moved to directing larger tasks, and may move to the goal level and beyond. Still, she said, a person has to decide which direction to go and where to take the work next as new feedback and data arrive.

She stressed that steering is not only about reading data. Much of it is making an opinionated call. She said we underrate intuition and what she called a kind of positive determinism about the future you want. You might choose a product direction not because the alternative is less viable but because you want the world to move that way. For now, she said, that opinion still has to come from a person. She also predicted that steering will become social: groups of people steering a shared set of agents together.

Lenny suggested that if everyone has the same tools, the human becomes the differentiator. Seshan compared it to fashion. Functional clothes do the job, but what you wear makes a statement partly by contrast with what others wear. She cited a line she attributed to Patrick Collison, or possibly John Collison: software is not like real estate, where money in reliably produces value out. It is more like filmmaking, where a big budget doesn't guarantee a good film and there is an auteur-like element of opinion and artistry. That, she said, depends on you or your team having something interesting to say. Lenny tied this to Marty Cagan's point that an initial product idea is rarely what ships. Seshan agreed and added that these discovery loops are getting faster, so the ability to form intuitions, gather what you need to form them, and act on them with people and agents is the key skill.

What agents need beyond intelligence: persistence, collaboration, and plumbing

Asked what internal ways of working might become common in the next few months, Seshan pointed to two shifts. First, people are working with agents at higher levels of abstraction. They give some steering and then "let the agent cook." Agents are starting to feel like persistent teammates. You work with them the way she works with someone on her team: they do a block of work, she gives input, they continue, and the two sync up at intervals and review each other's work in progress. She called this coworker model a much more natural interface and said OpenAI already sees a lot of it internally.

Second, most agent work so far has been one-on-one. It's her and her agent, maybe spawning some subagents, cut off from what colleagues are doing with their own agents. She described a period when people inside OpenAI would send each other screenshots of their Codex threads on Slack to explain how they had arrived at a number. That isn't a natural way to collaborate, she said. As more work runs through agents, the question becomes how people can work with agents together, and what interface makes that natural. She described the ideal as "a multiplayer game."

Lenny described the pace of progress as a "slow takeoff" of gradually growing trust. Seshan countered that the models are very smart, but said many of the gains that let agents take on larger tasks come from "meat and potatoes" work rather than intelligence alone. Local agents are convenient because they can see everything on your machine. Making an agent work in the cloud requires a large amount of infrastructure. Agents also need access to third-party systems where your data lives. She compared it to hiring a colleague and locking them in a room with no Google Docs, no Slack, and no company database: they wouldn't be very useful, and neither would an isolated cloud agent. She said data access, cloud infrastructure, and reliability feel more prosaic than questions about intelligence, but matter just as much for real-world effectiveness.

20:11

Ambition as the new bottleneck

Lenny brought up a recurring theme on his podcast: when easy things become trivial, what separates people and companies is how ambitious they are. Seshan said the people she sees using AI most effectively don't just automate rote tasks. They expand what they can do. She pointed to the old "unicorn" hire, a PM with strong product sense who could also code and design, and who was valuable because they removed the translation layers between functions. She said everyone now effectively has that superpower. She can generate designs, build a first prototype, work out a pricing model, and model scenarios herself. This lets her act more like an auteur and realize her vision at higher fidelity. Your ambitions, she said, are no longer limited by what you can personally execute or communicate.

The hardest part, she said, is expanding your own sense of what's possible in an "unreasonably short" time frame. She pointed to Patrick Collison's page at patrickcollison.com/fast, which lists historical projects completed with remarkable speed. What stands out to her now is that all of those projects happened before anyone could learn to build something almost instantly, summarize a difficult book in one question, or produce a CAD model of an idea. Her reasoning: if those projects were possible with older capabilities, we should expect an exponential increase in such work with what AI provides.

She also cited a point she attributed to Tyler Cowen: people underrate the effect of asking someone, "What's the more ambitious version of what you're doing? Could you do it faster, or at 10x the scale?" She said raising other people's ambitions has become a major part of the PM role. When a team proposes a timeline or a first version, part of the PM's job is to ask whether the ceiling is actually much higher.

25:14

Three internal memes: accelerate, mainline, feel the AGI

Lenny mentioned a meme that former guest Nick Turley had described: "Is this maximally accelerated?" Seshan confirmed it is an OpenAI meme and added one she and Andrew Ambrosino often ask their team: "Are you mainlining it yet?" That means: are you using the product all day, every day, to do your actual work, and bringing all your taste to judging whether it works? She described three questions as the memes of product development she wants to spread. Are we being as ambitious as possible about scope and scale? Are we moving as fast as possible? Are we mainlining it? Lenny called mainlining the new dogfooding.

She added a broader cultural one: "feeling the AGI." She described it as awareness that AGI is coming. She acknowledged there are many views on what that will look like, but said a shared belief in making AGI both real and beneficial for humanity is a big part of what brings people to the company.

27:25

Building for models two to three months out

The product principle she says she keeps in mind constantly is to build for where the models will be in two to three months. "You fail if you build for where the models are now. You fail if you build for where you think the models will be in a year," she said, and called both outcomes "equally wrong." Build too early and you're wrong. Build around a past model's capabilities and you're entirely wrong. Her conclusion is to put model capability at the center of the product and "get out of the way of the model" in the product constructs you create.

Asked how anyone can know what the models will look like in two or three months, she said it is not a pure black box. Research has focused efforts, such as improving the model at coding or writing in specific ways, so staying in close contact with research and aligning product development with the research agenda and roadmap is essential. Lenny recalled Kevin Weil's line that today's models are the worst they will ever be. Seshan called that reality "absolutely absurd."

29:33

Chat, Work, and Codex: one product in transition

Lenny walked through the current ChatGPT app: a dropdown for ChatGPT versus Codex, and a toggle between Chat and Work. Seshan said the north star is that users shouldn't have to choose at all. You type a task into a box, such as building an app to help podcast guests prepare, and the system picks the right harness and model. Understanding the product's limitations shouldn't be the user's job.

For now, she explained, choosing between ChatGPT and Codex is about whether you want a more development-oriented UI. Codex users aren't missing anything and should keep using Codex. People who come from ChatGPT and are curious about agents should use ChatGPT mode. Within it, Chat mode is the familiar conversation-and-search experience with improving models. Work mode is Codex under the hood, with some coding UI removed. For example, a worktree won't suddenly appear. Lenny asked whether Work mode includes anything beyond Codex, such as harness changes. She said the difference is really at the UI level. If you ask Codex for a complex financial model or a six-month revenue forecast, it will do as well as Work mode. What differs is how the chain of thought is displayed and how much technical detail you see. She gave OpenAI's corporate finance team as an example of Work mode users. She said they have turned tasks that used to be manual, or that depended on one person's deep expertise, into things the whole team can do, and have raised the team's ambitions on timelines and scope.

On balancing a product used by about a billion people with fast-moving experiments, she said a goal of bringing Work to ChatGPT on the web and the desktop app was to give those users the power of agents. This is where she laid out her three eras. Chat was the first. Agents, so far mostly coding agents, are the second. A third era, which she said "might come soon," is working with a persistent coworker that gets things done with you, possibly alongside other people. She said the near-term challenge is introducing agents to a billion people who may never have used one, without making them understand concepts like harnesses.

She contrasted this with her earlier career. At previous companies, "polish was king." Getting every interaction right mattered more than shipping early, because timing didn't change outcomes much, and if every corner wasn't polished you might as well not ship. In this era, she said, when you are convinced something is transformative, getting it into users' hands beats perfect. She acknowledged the team has a lot to do to make Work easier for chat users, including people who use ChatGPT for consumer tasks rather than productivity. When Lenny noted the early confusion around the launch, she added that it's always possible to iterate more before launch and that there is plenty they can do better. The key, she said, is iterating quickly and listening to the right signals, ideally before launch.

Why Codex's reputation shifted

Lenny said he had noticed a shift on Twitter from Claude Code to Codex over the past few months and asked what had changed internally. Seshan cited the saying about chopping wood and carrying water before and after enlightenment. In her account, nothing fundamental changed. The team that built the Codex app had always been user-focused, iterated tightly, and mainlined the product. What changed was that the market and users noticed. She said everyone building the app is a developer who uses it for development and fixes their own problems as well as those of colleagues and users. She gave the team, and especially the desktop team, full credit. She described them as independent, founder-like people who notice something that should be better, build it, test it internally, iterate if people don't use it, and then ship it externally. When Lenny remarked that the answer was about humans rather than AI, she agreed.

42:32

Blurring roles and the unresolved question of craft

Lenny asked about the confusion people feel as roles overlap. Designers, marketers, and PMs are unsure what they are now responsible for. Seshan said she has always liked startups because roles have few boundaries, and she described Stripe as very much that way, with anyone able to do anything. She sees AI capabilities as finally catching up to that mentality. What matters to her is that someone is clearly accountable, a DRI, for whether the product is used, wanted, high quality, and effective. Whether that person is an engineer, designer, or PM doesn't matter, and other work can be picked up based on affinity and capability.

She also expressed real uncertainty. She loves the craft of product management that people like Shreyas Doshi, Marty Cagan, and Shishir Mehrotra have written about, and she understands the worry that fluid roles mean losing the chance to hone a craft. "I truly don't have an answer for that question," she said. Some parts of craft are being abstracted away by models that may do them better than individuals, and craft shifts to applying skill elsewhere in the product or discipline. She said she is still working out how to balance her enthusiasm for how effective people can now be with her love of craft. She noted that engineers used to enjoy handwriting code and rarely do so now, and that people mourn the flow state of writing code by hand. She called it a tough transition.

46:09

Where humans remain valuable

Asked where human brains will stay most valuable over the next few years, Seshan gave three answers, while noting she can't predict what the models will do. The first is accountability. You can think of your agent as a report, but a person still owns the outcome and decides whether it was high quality and what was intended, especially in regulated industries or settings that need a direct human interface. The second is expression. She returned to the film analogy: the best films aren't the biggest-budget ones, and software has authorship. Choosing what to build and how it feels is, in her view, a deeply human question. The third is how people care for and relate to each other. Talking with teammates, building shared enthusiasm, learning together, and raising each other's ambitions has become more important in her work than ever.

48:30

How she uses AI: Sites and /visualize

Lenny noted the "overhang" between what AI can do and what people actually use it for, and asked for concrete examples. Seshan said she now builds Sites constantly. She described Sites as a product for creating hosted sites with a database. She uses them as presentational artifacts at work and for much more. She built a game the team played together. For a recent backpacking trip, she built a site showing the route and elevation, where everyone on the trip entered their food. She said Sites realize Alan Kay's 1960s vision of malleable personal software. Earlier tools like Notion tried to get there by configuring blocks, but with Sites, she said, it is literally a prompt. Sites can be shared, can update automatically, and can use internal data for things like metrics dashboards, and she called them a more dynamic presentation surface than a slide deck. You just ask Codex, for example, to "create a site that is a mafia game for my team." Hosting is handled for you, and you can make a site public, team-only, or private. She said you can create them through Work, Codex, the web, or mobile, and that making sites has replaced much of her former habit of producing docs and sheets.

Her second tip was the /visualize command in Codex. For example, asking it to visualize your ChatGPT usage so far pulls in your history and produces a visualization. She said she has lost count of the times she needed to turn charts and data into something that told a clear story, and that /visualize makes this "surprisingly delightful."

During the conversation Lenny started a Site about Seshan. By the end it had produced a designed personal page with quotes and themes such as "big conviction, small teams" and "start with the buyer." She liked it, though she was amused that the header photo appeared to be her Stripe badge photo from when she was about 19.

52:41

Writing as thinking versus writing as reporting

Lenny passed along a prompt from Brie Wolfson, who said a "Tara brief" is iconic. Seshan distinguished two kinds of writing. Writing as reporting covers status updates, weekly summaries, and launch plans, and she happily automates it with models. Writing as thinking covers briefs arguing for a product, a strategy, or a "spicy take," and she said she will never automate it. For her, outlining, turning an outline into prose, cutting, and revising is how her ideas take shape. She thinks most people paint with too broad a brush, either always or never using models for writing, and considers both wrong.

Her process at Stripe, which she described as strongly writing-oriented and one of the few places where a brief could go viral internally, was to go deep on a brief, refine it, then shop it around and ask people to attack it. She would strengthen it and take it to the next person, repeating the cycle. She did this many times to start new product areas, propose changes in direction, or analyze problems. She mentioned Jeff Weinstein as another Stripe colleague known for writing briefs. A former manager told her to write a doc to about 70% and bring it to the people whose buy-in she needed to get it to 100%. Very few great people want to engage with a perfectly polished idea, she said, because their own ideas "just bounce off of it," while rough edges invite them to shape it with you.

At OpenAI, she said, she still writes to think, often hundreds of docs, but mostly for herself. She said a long doc no longer signals careful thinking, since anyone can now produce one without having thought something through. She described this as perhaps her biggest and most jarring personal change. She used to think in a document and then translate it into a presentation as proof of thinking. Now she favors "mocks not docs" or "prototypes not docs," and ideally results: "we ran an A/B, here are the results, this is why we should go in this direction."

Avoiding "AI brain rot"

Asked how she avoids over-relying on AI, Seshan said the writing-as-thinking discipline is her main safeguard. She also follows a personal rule: if she will ask people to read a document, she should invest at least the combined time they will spend reading it in writing it. Likewise, she preps for a meeting for at least the combined time attendees will spend in it. She said she doesn't rely on the model to polish her prose, adding that she doesn't think it really does that well, and especially not to generate a first draft. She does use it heavily for summarizing and converting content between formats. Her summary: "I start myself and I end myself." In the middle she may use AI to research specific points, pull in data, or push back on ideas.

1:00:22

The lesson from Sutter Hill: product-marketing fit

Seshan described Sutter Hill Ventures as intentionally illegible. Its website shows almost nothing, and it operates quietly, yet it is behind major successes such as Snowflake through the incubation model started by partner Mike Speiser. What struck her was that people treat finding product-market fit and building a tens-of-billions-dollar company as a dark art of luck and chance, while Speiser has done it repeatedly, which suggests there is a playbook. In her account, the firm has learned to be right about calling shots and about the daily compounding work of building a company: setting up enterprise sales, positioning, and assembling founding teams. She singled out recruiting and mentioned an internal tool she called Reticle, which maps the people the firm has worked with and the ten best people each of them has worked with. She said she went there because her career has been about finding product-market fit repeatedly, and Sutter Hill had figured out how to do that for B2B products.

Her main takeaway was that she had underrated what she called "product-marketing fit." The way you talk about and position a product can come before building it. It should combine a deep understanding of the technology with an understanding of the enterprise sales process. Before committing to a product shape, you should pitch around 100 people, refine the pitch, and get the narrative of why the product is transformative right. She admitted she used to see product marketing as glue between functions, and came to see excellent product marketing as work that can determine a company's success.

1:05:05

Knowledge work is not coding: verification and the model as collaborator

Near the end, Seshan raised an issue her team is working through with ChatGPT Work: knowledge work and coding are fundamentally different. Coding is output-oriented, so you can check a result with tests or by running it. Knowledge work can't be verified by looking at the final deck. You can't see "90% success" in a slide and simply believe it. You need to see the process, inputs, and reasoning. So, she said, much of the team's work, now and ahead, is adapting the product for knowledge work: making ChatGPT a collaborator, showing work in progress, surfacing citations and inputs, and letting users follow the model's path so they can trust the result. She listed open questions. Should the chain of thought show more citations? Is the thread interface, well suited to coding, the right surface for knowledge work? Lenny compared it to pitching an executive, where showing the steps behind a plan is much of the pitch, and added that context, such as whether the agent can see your email and docs, is part of the same problem. Seshan said that as the team thinks about bringing human collaborators into agent work, it also needs to make the model itself more of a collaborator.

Lightning round

For books, Seshan recommended Barbarian Days by William Finnegan. She took from it that you can devote your life to something without ever being great at it, and can pursue excellence knowing you won't reach it. She also recommended Anna Karenina, which she has read at different ages. At 13 she followed the plot, at 17 the European history and class dynamics, and at 30 she saw it as a story about a woman and about people. She connected this to the need to see the same things through new lenses as we grow and change careers. She also said she loves The Power Broker and suggested reading long classics chapter by chapter with a slow-read Substack, which she said had covered War and Peace and Wolf Hall. Lenny added the 99% Invisible book club series on The Power Broker.

For film, she chose Christopher Nolan's The Odyssey. Her "hot take" is that it is about AI and how it transforms society, and she said Nolan bridges artistry and commercial success like no other modern director. She also recently watched Akira Kurosawa's Rashomon. She noted that it pioneered telling a story through conflicting perspectives while working in black and white in the 1950s, and she drew a lesson about ambition: with a hundred times Kurosawa's tools in her iPhone, "what's my excuse" for not making better work?

For AI products outside OpenAI, she named software her friends build for small groups, part of what she called the "cozy software" movement. A friend named Sebastian built an app that turns any content into a podcast and drops it into your Apple Podcasts feed, and a private social network for their friends, called GATS, which she compared to a private Twitter. Her motto comes from Toni Morrison's essay "The Work You Do, the Person You Are": do the work well, for yourself and not the boss; you make the job, it doesn't make you; your real life is with your family; and you are not the work you do, you are the person you are.

On the Thiel Fellowship, she called it an inflection point in her life and a moment when someone raised her ambitions and told her she didn't have to follow the path she was on. Her cohort's pitches were filmed for a CNBC documentary, so her 19-year-old pitch is on YouTube. She mentioned Dylan Field from her cohort and fellow fellow Ari Weinstein, whose company Sky was acquired by OpenAI and who now leads much of OpenAI's computer-use work.

For her plug, she encouraged listeners to try Work in the ChatGPT desktop app, on the web, or on mobile, for example by asking it to build a Site about themselves or to visualize their ChatGPT usage. She said the most magical experience is starting a task on your phone, going through a subway ride without service, and finding the work finished when you come out, because it runs in the cloud rather than on a laptop you have to keep open. She confirmed that cloud execution works across all platforms, not just mobile.