The Skip Podcast
00:17:34 · Dianne Penn
[00:17:34] S0: I think it's relatively product development is relatively more bottoms up because there are so many ways that this technology and products around it can generalize. For example, even on something like Claude Code, there were customers or there were API customers who utilized some models for autocomplete for a long time before it. Right. So it wasn't that just one day coding became agentic. It was that there was a different sequence into people experimenting both internally and externally. What you saw was in particular the paradigm of the terminal and having allowing the model to actually do more agentic loops really started working with a combination of a product experience harness and also the model. I think in terms of product priorities, I think it's very around like what are some themes or areas that we are really stubborn about and how do we quickly get learnings into is the user experience or the outcome with the current set of technologies feasible? And are people finding like the magic, like we call it like finding the magic enough? And we have been also much more concentrated in terms of our approach on prioritizing for business, for enterprise, which tends, I think also to have a more stable set of needs and requirements compared to, let's say consumer, which is very dynamic and changing quickly. But even within the enterprise side, like there were times where we debated, should we have a fine tuning API? And one of the philosophies that we ended up with was, well, the model, the core models are improving so quickly. So by the time it takes a team to figure out how to post train themselves to then make it really good and then deploy it, you might be two to three model generations behind. So you'll have to start over. So is that the right investment for us or the users and customers? And so allowing to kind of asking ourselves a question, what might change in three months? What might change in six months? Helps us figure out like what might be worth shipping. But I think a lot of the actual prototypes, like there's a lot of prototypes internally that actually we don't end up shipping externally because we're trying to mostly create ideas or experiment, first.
00:20:05 · Nikhyl Singhal
[00:20:05] S1: You know, I love this term that you used around we want to be stubborn in certain areas. I think that's to some extent a better phrasing than we know we need to be opinionated as strategists, product leaders, executives. Your comment, I can imagine, you know, asking our audience, like, what are you stubborn about when it comes to areas of investment in the next six to twelve months, and then perhaps what are you more loosely held on, or perhaps what you know is going to change and you have to be more dynamic. This notion around stubborn opinions and deep execution are two areas that I think come through with both your career, as well as maybe the type of team that you're building. I'm curious around, you know, there's a number of folks that are listening to the call. Some are early in career, some are maybe ten, fifteen years, and they have held a product management role that they know is changing quite a bit. And, you know, one goal of today's conversation would be to help counsel them both on what you see within Anthropic and what has succeeded when it comes to product management, but also how does that influence your opinion on what product management maybe you need to do in other companies? So when you think about what's worked and what may have not worked as you've hired people over now several years, you know, give us a little bit of a flavor of, you know, the skills that you look for and maybe what resonates in an organization like yours.
00:21:37 · Dianne Penn
[00:21:37] S0: A lot of my PMs actually come from pretty diverse or different backgrounds. There's actually many people who have kind of similar to me, what might seem like a like meandering walk of different careers rather than like one clear, this is the ladder of like done the same job, but at higher levels within the same company. I think what that allows people to bring is like adaptability, agility, because we're constantly learning. Our assumptions are constantly being challenged. And so there's a layer of folks who are really good at learning or picking up new things or have a track record in their career of either being the first product manager at X startup. I tend to find that to be like a really powerful profile because you're a product person, but you're likely also the first customer success person. And you're also potentially have been the IT person. And you've also might have had to do business development. Just a number of hat wearing that somebody has to do as a first PM with an x has been like a profile that's worked really well because of that specific, like, agility. I've hired folks who were former researchers, folks who actually have been at the same company for a long time, but with the recognition that like they want to try to lean really far out of a set of assumptions about how product or how work and having impact for users could look like. I think it's not necessarily day one where you come in and you do the exact same job. And what I tell the team in their onboarding plan is the first two months here should feel like some of the hardest of your career. That actually means you're doing it right because of the velocity and pace that we're working, the ways of working to how to hold the short term with the medium to long term. And with a medium to long term that is changing dramatically. And to deliver on a product plan or a set of outcomes or a strategy for your area, a roadmap for your area. That type of challenge is stretched, especially stretching people in the beginning. What I've seen being successful are those who really try to rise to the challenge. And I try to give actually really hard initial ramp ups. And for folks who really then ramp up quickly, then they kind of get onto the acceleration. And for folks who are like, this is really hard. I have these reasons why I couldn't do X, Y, and Z.
00:24:16 · Dianne Penn, Nikhyl Singhal
That's who ends up struggling more. Like I kind of start to get a sense of that within the first one to two months. It's really like a growth mindset. [00:24:26] S1: What's an example of folks that when they say to you that, Hey, I'm finding it really a struggle. Is it, are there skills to unlearn? Is there boundaries that they have? Is there sort of a way of thinking a mental model? Like what's, what's the barrier? What's the prison you find themselves in?
00:24:41 · Dianne Penn
[00:24:41] S0: I think part of it is, especially for PMs who are coming from large companies, it's very hierarchical from what I've seen where, you know, if your VP says X, then you do X all the way down all of the chain. And there's less of questioning of like, is the right x still the right thing? And I think that's very different than like a traditional academia, which is like the closest analogy to how research works, where like the junior first year PhD student might question their advisor. And so for folks who kind of put aside the hierarchies of how to work that they are used to, and they actually come in and say, hey, I Jared, who's our chief scientist, hey Jared, I know you wrote about X. Here are some assumptions that I think you are missing. This is the reason why. This is why it might actually be more useful for users. Like being willing to kind of speak up very early to kind of enter the discussion rather than assume that like everybody has it figured out and doing that in a way that is curious and trust building, right? Cause what you don't want is people to have very hot takes of like, you're wrong and doesn't really go into details. And so what you really want is folks who join the Discworlders, add to it, build on it, change it in some way, push on people's ideas. Those tend to be like, I think really impactful because that means they've like done their own thinking and come up with like sort of the so what to just three steps when either even others haven't or be willing to try. Like, it's just that persistence on trying. Because the first couple of ideas everybody comes up with might be things we thought about two to three years ago. It's just there was a history of why we didn't do X, but willing to go beyond the surface ideas to do the hard homework, question assumptions in a graceful manner, and then coming up with like a unique point of view, those folks tend to be successful.
00:26:53 · Nikhyl Singhal
[00:26:53] S1: Yeah. So it's the soft skills of communicating that and influencing it's the desire to be both curious as well as opinionated, as well as perhaps a little stubborn. But also I think that you didn't say that those opinions are always right. I think your point was the characteristic is to question the answer of we've considered it and it didn't work out might be an okay resolution. And perhaps now there's another time to look at the answer or the question again. But I think your point is that that is the pattern and the skill that tends to then play out as people get onboarded and they get more comfortable. This notion of questioning assumptions, questioning even authority to some extent, is that because the models are changing so frequently and that's a necessary skill for this type of work? Or is this a anthropic cultural observation that this company tends to promote that type of value?