Lenny’s Podcast102 min
Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future
Dianne Penn · Jul 26, 2026
Key learnings
- Treat evals as the new PRDs: turn vague user complaints into concrete, reproducible test sets that researchers can act on and…
- Dig into user transcripts, not just pixels, to find where the model actually failed, such as wrong tool calls, bad retrieval, or…
- Keep strong conviction about a theme or area while staying loose about the specific prototype, and revisit bets across one to two…