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Diane Penn: evaluation

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

“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.”

— Diane Penn

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Speaker
Diane Penn
Attribution
Verified speaker
Claim type
evaluation
Recorded
26 Jul 2026
Publisher
Lenny's Podcast

Transcript context

…Yeah, that makes sense. I would imagine you'd want as many customers if people are using this thing as possible. This episode is brought to you by Mercury, radically different banking, loved by over 300,000 entrepreneurs, and now with Command. I've been a customer of Mercury's for over six years. I have never once though about leaving. Mercury is basically what happens when banking is built by product people, not by bankers. They make it so easy. Dare I say fun to send invoices, move money around, set up virtual cards for folks on my team. Does your bank have an API, a terminal native CLI, or an AI-ready MCP server? I don't think so. And just recently, they launched Command, a conversational interface built directly into Mercury, which acts as your financial operator. I've been using Command to transfer money around, to figure out what categories I've been spending the most money in, analyze my cash flows, and just today I used it to find out how much I've made from a specific sponsor over the past year. I just ask, "How much have I made from X over the past year?" 10 seconds later, I have an answer. It is so freaking cool. Visit mercury.com to learn more and apply online in minutes. Mercury is a FinTech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC. I want to talk a little bit about how the product role is changing and who is doing well in this new world now that AI is such a core part of our life. When you're hiring PMs, product people, when you're looking at people that do well in today's world, what are some things that you notice? What are you looking for more most? What are you looking for more? What's trending up in what you find is important and what's trending down? We actually, on my team, have not changed our hiring loop for three years now. 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. And this is really rather than pattern matching what you used to do in, let's say, consumer product or B2B SaaS, but actually figuring out in this moment for this user group with this technology, what is the user value? Is there an example of that? A lot of people hear first principles thinking, they're like, "Yes, I got it." I'm good at this. What's an example of someone having really demonstrated really good first principles thinking?…

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