Dianne Penn

speaker

606 appearances 1 recordings 1 series first heard Jul 2026 last heard 26 Jul

Dianne Penn’s voice in public audio — every appearance, attributed to the second.

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Recordings per month over the last 12 months — 1 in all, peaking in Jul 2026 with 1.

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Lenny's Podcast: Product | Career | Growth · Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn · 26 Jul 2026 podcast

Here, you have to sweat the tokens as much as you sweat the pixels.

And so one activity we have on the team is reading the transcripts and understanding what was the trajectories that failed

very deeply to then say, was this like a hallucination?

Was this cloud being overconfident?

So like the theme of the failure actually has a lot of nuance.

And then that allows you to build a description, a like sustained description of that pain point.

So that could be essentially in a new eval.

And is it eval on distribution, right?

Is it capturing both the positive situations where this is failing and also areas when it should actually not fail?

And then bring that back to, let's say, research so that we can make the improvements and actually measure the quality of, okay, when we have Opus 5.5, is this area improving or not?

Is Claude now able to identify the right places in the document?

and pull the right synthesis out.

So it's just the actionability and shorting the distance to actionability for our stakeholders and partner teams like researchers to take action on.

We actually pioneered this concept within Anthropic.

So one of the early examples is the early Cloud models were not very good at following specific schemas, so things like outputs and JSON.

And now that is fundamental to Cloud being able to be a good agent.

If you can't output a certain format, you don't know how to access APIs, you can't call tools, et cetera.

And so the initial end-to-end was I was hearing feedback around, you know, cloud two days.

Cloud was not very good at following instructions.

So then digging in with users, what do you mean by cloud is not good at following instructions?

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