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Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

26 Jul 2026 39 published claims 2 attributable people
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Speakers in the public record

Diane PennLenny Rachitsky

Claim mix

belief 15evaluation 12recommendation 6uncertainty 3observation 1prediction 1commitment 1

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Every row below preserves an exact excerpt. Identified speakers are linked; unresolved voices are labeled and excluded from people counts.

Claim ledger

The useful parts, with receipts.

39 published records

01 / recommendation

Likes How to Raise an Adult.

“One personal one, I really like How to Raise an Adult. So I'm a mom. I think a lot about what is the things that I want to instill in my kids. And that book is really helpful for describing, we're not trying to raise children, we're trying to raise adults. So just the framing of what does that mean? And what does it mean, what are the characteristics that we want to hone and harness and foster in our kids? The other book that I was listening to on Audible recently is Incorrigible by Eric Reese. So the author-”
Speaker
Diane Penn
Publisher
Lenny's Podcast

02 / recommendation

One personal one, I really like How to Raise an Adult. So I'm a mom. I think a lot about what is the things that I want to instill in my kids.

“One personal one, I really like How to Raise an Adult. So I'm a mom. I think a lot about what is the things that I want to instill in my kids.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

03 / evaluation

Yeah. I think some people are like, "What's the big deal?" The fact that everyone at Anthropic is raving about it tells me something important is going on here.

“Yeah. I think some people are like, "What's the big deal?" The fact that everyone at Anthropic is raving about it tells me something important is going on here.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

04 / evaluation

It used to be the way founders push people like, what if we 10X this? And I love what I keep hearing is it's like, how do we go 1,000X from this idea?

“It used to be the way founders push people like, what if we 10X this? And I love what I keep hearing is it's like, how do we go 1,000X from this idea?”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

05 / evaluation

And my grandfather always says, no matter how far you go, there's always another level, which is, I think, a really good way, though a pretty intense way of describing his life philosophy.

“And my grandfather always says, no matter how far you go, there's always another level, which is, I think, a really good way, though a pretty intense way of describing his life philosophy.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

07 / evaluation

So what we actually look for and the traits and how we evaluate generalists like PMs, generalists like research, product managers have actually been the same. So I think some of those traits, number one is first principles thinking.

“So what we actually look for and the traits and how we evaluate generalists like PMs, generalists like research, product managers have actually been the same. So I think some of those traits, number one is first principles thinking.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

08 / evaluation

I love how many of these answers connect. So what I'm hearing here is just working with other people, relying on other people, helping each other out when things get crazy, which is a similar answer you had for just how to find the joy and fun in this work.

“I love how many of these answers connect. So what I'm hearing here is just working with other people, relying on other people, helping each other out when things get crazy, which is a similar answer you had for just how to find the joy and fun in this work.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

11 / belief

One thing that I think I feel pretty strongly about is in order to be good managers of teams and PMs working with this technology, you have to be really hands-on yourself and have spent not just time tinkering, but actually shipping with this technology.

“One thing that I think I feel pretty strongly about is in order to be good managers of teams and PMs working with this technology, you have to be really hands-on yourself and have spent not just time tinkering, but actually shipping with this technology.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

12 / belief

What does it mean then to have a discontinuous bet? And I think one approach that we're taking this year is you can be very strongly held opinion about the theme or the area, and then more weakly held about the exact prototype.

“What does it mean then to have a discontinuous bet? And I think one approach that we're taking this year is you can be very strongly held opinion about the theme or the area, and then more weakly held about the exact prototype.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

13 / belief

Now that that's improved a bit, then it's, well, now it's these other areas actually become more of the rough edges. And so I think we're in one of those moments worth writing where we need to actually just focus and prioritize on training the models to be great at this area.

“Now that that's improved a bit, then it's, well, now it's these other areas actually become more of the rough edges. And so I think we're in one of those moments worth writing where we need to actually just focus and prioritize on training the models to be great at this area.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

15 / uncertainty

I remember when Anthropic first launched, this was, I don't know, the first model when it launched years ago, three years ago, something like that.

“I remember when Anthropic first launched, this was, I don't know, the first model when it launched years ago, three years ago, something like that.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

16 / belief

We know that the models could write great essays or could write long form writing, but individual pain points of what can you actually solve with that and bring it to a user level that people can use, I think is something that is more exploration or experimentation based.

“We know that the models could write great essays or could write long form writing, but individual pain points of what can you actually solve with that and bring it to a user level that people can use, I think is something that is more exploration or experimentation based.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

18 / belief

Most traders, I think, are in front of a terminal. They're much more doing analyses on their computers, but it's still very, I would say, male-dominated.

“Most traders, I think, are in front of a terminal. They're much more doing analyses on their computers, but it's still very, I would say, male-dominated.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

19 / belief

I think the role of people who are user-centric, who go into the details of understanding what users are trying to accomplish, bubbling that up in an actionable manner and doing the relentless work to do that, that, to me, is a core of a product person.

“I think the role of people who are user-centric, who go into the details of understanding what users are trying to accomplish, bubbling that up in an actionable manner and doing the relentless work to do that, that, to me, is a core of a product person.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

21 / belief

I think the folks that would be most successful, regardless of their level, are people who love working with AI and are exploring and experimenting. And carving out the time, not just for the experimentation, but actually hands-on shipping end-to-end, getting the user feedback, I think has to be fundamental for everyone.

“I think the folks that would be most successful, regardless of their level, are people who love working with AI and are exploring and experimenting. And carving out the time, not just for the experimentation, but actually hands-on shipping end-to-end, getting the user feedback, I think has to be fundamental for everyone.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

23 / belief

I think there's product overhang and user overhang, to maybe put it in our PM language, even on today's models. And I think there's a lot that we could be exploring on our current opuses and definitely with Fable, for example.

“I think there's product overhang and user overhang, to maybe put it in our PM language, even on today's models. And I think there's a lot that we could be exploring on our current opuses and definitely with Fable, for example.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

24 / belief

I think that's also why Twitter is so useful for a lot of this is you see other people sharing what they've done, and it inspires you to come up with your own little ideas.

“I think that's also why Twitter is so useful for a lot of this is you see other people sharing what they've done, and it inspires you to come up with your own little ideas.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

28 / belief

I think a lot of the most successful researchers and research leadership at Anthropic are folks who are really strong first principles thinkers about problems.

“I think a lot of the most successful researchers and research leadership at Anthropic are folks who are really strong first principles thinkers about problems.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

29 / belief

I think the best way to find my work, my team's work is really the Anthropic blog and when we're publishing new models, new product experiences.

“I think the best way to find my work, my team's work is really the Anthropic blog and when we're publishing new models, new product experiences.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

30 / prediction

I think the product question and how we interact with these internally is, I think as you mentioned, as frontier models become more capable, the safeguards and the ways of red teaming and testing and the pre-release process also needs to evolve and adapt quickly to address that.

“I think the product question and how we interact with these internally is, I think as you mentioned, as frontier models become more capable, the safeguards and the ways of red teaming and testing and the pre-release process also needs to evolve and adapt quickly to address that.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

31 / recommendation

If you only measure revenue and then that's how you're going against. But if you have other better metrics, that's actually the way to sustain the values you care about.

“If you only measure revenue and then that's how you're going against. But if you have other better metrics, that's actually the way to sustain the values you care about.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

32 / evaluation

Here's what they're talking about computer use; here's what they're talking about with this limitation of this UX situation. And you made this really interesting point that you have to have fun with it, which is not easy for a lot of people because they're pushed to use AI or they just don't know exactly what to do with it.

“Here's what they're talking about computer use; here's what they're talking about with this limitation of this UX situation. And you made this really interesting point that you have to have fun with it, which is not easy for a lot of people because they're pushed to use AI or they just don't know exactly what to do with it.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

33 / evaluation

I think there's some really interesting graphs in the original scaling law papers. And I think folks are very familiar with the scaling loss in the lens of as you add in more compute and data, what's called loss, AKA the loss from next token prediction goes down.

“I think there's some really interesting graphs in the original scaling law papers. And I think folks are very familiar with the scaling loss in the lens of as you add in more compute and data, what's called loss, AKA the loss from next token prediction goes down.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

34 / recommendation

I think one area that it's not more recent, but one that I bring up a lot with the team and I think we could do more on using AI is just how to use it to also have better conversations with each other, to be better managers.

“I think one area that it's not more recent, but one that I bring up a lot with the team and I think we could do more on using AI is just how to use it to also have better conversations with each other, to be better managers.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

35 / evaluation

I think one example is I think you think of a product manager as I own product strategy and delivering user value, but I demonstrate day-to-day by writing a PRD or writing a product vision doc.

“I think one example is I think you think of a product manager as I own product strategy and delivering user value, but I demonstrate day-to-day by writing a PRD or writing a product vision doc.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

36 / recommendation

How do we invest in explaining the differences to users? So a lot of the experiences I think of being in that exponential is that pace, understanding how you operate and make better decisions, and then applying that first principle's thinking to then do something that maybe we pull up a plan that we're expecting a few months from now, but now the model can actually do and work on and actually bring that to users.

“How do we invest in explaining the differences to users? So a lot of the experiences I think of being in that exponential is that pace, understanding how you operate and make better decisions, and then applying that first principle's thinking to then do something that maybe we pull up a plan that we're expecting a few months from now, but now the model can actually do and work on and actually bring that to users.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

37 / commitment

That to me was one of those maybe hidden inflection points of we were starting to find our identity, that we could build products, build experiences that were different from what our competitors had seen, what was already out there. And I think that obviously Labs, Claude Code, et cetera, we then started to identify ourselves as would we actually think the world, how to think about AI, how to bring that closer to the public.

“That to me was one of those maybe hidden inflection points of we were starting to find our identity, that we could build products, build experiences that were different from what our competitors had seen, what was already out there. And I think that obviously Labs, Claude Code, et cetera, we then started to identify ourselves as would we actually think the world, how to think about AI, how to bring that closer to the public.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

38 / evaluation

On some of these other areas, we're not quite there yet. And so I think you're seeing us shift things like Claude Science investing in these areas because those are areas that I think is just bring this technology to society and having a positive benefit for society.

“On some of these other areas, we're not quite there yet. And so I think you're seeing us shift things like Claude Science investing in these areas because those are areas that I think is just bring this technology to society and having a positive benefit for society.”
Speaker
Diane Penn
Publisher
Lenny's Podcast

39 / recommendation

Mentions personal use of Claude.

“A lot of actually thinking process and writing process are tied together for me personally. And so I think there are ways where I use Claude to augment my thinking, but what I want to make sure, and maybe this is what you're describing, is Claude doesn't take over all of my thinking for me.”
Speaker
Diane Penn
Publisher
Lenny's Podcast
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