Lenny's Podcast: Product | Career | Growth
00:19:31 · Casey Winters
[00:19:31] S0: If you're super enterprise, it's kinda the opposite. Right? Each customer, first off, is sophisticated and tend to be rational. They're paying you, like, 6 figures or more, and you could talk to the customers and sales who knows the customers really well directly, And they tell you what they want. They tell you what they're willing to pay for. You build it. They pay you. Bing bang boom. Right? It's not obviously as simple as that, but, you're basically doing the research directly with the customer and with the sales team and and translating that to things that are strategic to to the business. And I I would say those are the two extremes probably most people are familiar with. But we now have a lot of companies in the middle where they have more customers. Those customers are more sophisticated. They're consumers. They're maybe employees at companies or they're small businesses. And that's where you have to be more more nuanced, and and this is, of course, where Eventbrite was on, hey. When do I really lean in on research? When do I lean in on data? When do I pay attention to internal feedback? So, you know, for Eventbrite, we really tried to focus research on the b to b side of Eventbrite where the problems seem big but not well defined enough. Or that problem's well defined but we just really don't feel like we have the right solution yet. And, you know, if research is gonna be, a scarce resource inside the company, which I think it will in most places, you have to figure out where it's a high leverage area, which means either really big problem, we don't we don't understand it well enough, or we know the problem's big, we understand it well, but we're just not sure if our solution's gonna, at any way, like, you know, hit the mark.
00:21:06 · Lenny Rachitsky, Casey Winters
[00:21:06] S1: Makes me think about some of the best researchers I've worked with, and they often tell me, like, we don't need to do research on this. We have enough information. Like, we we have other things we should be doing. [00:21:13] S0: I I love it when they say that. Yes. [00:21:15] S1: Yeah. This would have been a really good segue to another topic I wanna talk about, which is around gut instincts versus team expertise, which we're gonna get to, but I have a couple more questions along these lines. Sure. You talked about interviewing PMs at Whatnot. Can you actually describe Whatnot just because you mentioned a couple times just so people know what we're talking about? [00:21:31] S0: So Whatnot's a a live streaming marketplace, mostly focused on the collectibles market. So, you know, sellers, whether it's like, you know, baseball cards or women's handbags or sneakers, you know, they'll go live on video and show you the products they have that they're selling, and people who are watching the streams can engage with the sellers and bid on, you know, different items. So kind of like Twitch meets eBay would be the you describe it. [00:21:54] S1: Awesome. And I'll just mention I'm a tiny angel investor in that company. [00:21:56] S0: Oh, that's why you brought it up. Okay. I get it. Yeah.
00:21:56 · Casey Winters, Lenny Rachitsky
[00:21:56] S0: Oh, that's why you brought it up. Okay. I get it. Yeah. [00:21:59] S1: I just wanted to make sure people understood what this word was because it's like a a fun word, whatnot. But what I wanted to actually get to is you said you were interviewing a lot of product managers for them. Yeah. What is your approach to interviewing PMs? What do you find is a is a really good signal for someone that's gonna be successful? [00:22:14] S0: I feel like the whole thing's gotten so performative. [00:22:17] S1: Mhmm.
00:22:17 · Lenny Rachitsky, Casey Winters
[00:22:17] S1: Mhmm. [00:22:17] S0: It's like interviewing is handing out Oscars based on who's prepared the best tell me about a time response versus actually assessing, like, who can choose the job we're hiring for. So it's like most PMs are better PM interviewers than PMs now. There's this quote from a movie called The Way of the Gun. I don't know if you've ever seen it. Nope. But Benicio del Toro says in it, it's like, these days, they wanna be criminals more than they wanna commit crime. Mhmm. And I think about that quote a lot when it comes to interviewing. So I would say I'm a bit contrarian here in my approach. I don't ask about your work history. I don't care about your perfectly practiced answers. I'm gonna give you real scenarios that I expect from the role. I wanna hear how you'd approach them. And if you can't come up with a few reasonable ideas, figure out how to test them quickly without analyst support or research, I'm just not interested. And I'm not saying this is a perfect approach. Interviewing is a very lossy format. But the more I can see them do the job we're hiring for with questions, whether it's a presentation, a prompt, that gets me the most comfortable that they know the job they're signing up for, that they've shown in a practice scenario they can do it, and they actually enjoyed it in some way. [00:23:28] S1: Are there, like, red flags you look for in these interviews? Like, one is maybe said over, like, I can't even begin to answer this without research and data. Is there anything else?
00:23:28 · Lenny Rachitsky, Casey Winters
[00:23:28] S1: Are there, like, red flags you look for in these interviews? Like, one is maybe said over, like, I can't even begin to answer this without research and data. Is there anything else? [00:23:36] S0: Some things I pay attention to is if they're talking about solutions that are gonna take a long time to get signal from. [00:23:44] S1: Mhmm. [00:23:45] S0: You know, whether it's months and months of engineering time before you actually, you know, see the impact on users or or the business, I think that's, you know, always great. If they're not factoring in the amount of time it will take, in general is not, you know, a good sign. And not thinking a bit more holistically about the types of metrics they expect to improve versus track to make sure, like, they haven't gone down. Those are some things that I pay a lot of attention to. [00:24:11] S1: How much do you think, they're intimidated by being interviewed by Casey Winters? How much do you think that factors in? [00:24:16] S0: I think you overestimate my importance or awareness in the community. I think most people have no idea who I am when they start talking to me. [00:24:25] S1: Mhmm. Well, I don't know. Another thought is there's this mean that g p t four is gonna... Or five or six or 10 is gonna replace product managers. And anytime some new feature comes out, people put out these videos of, oh, look. They're doing all the PM's jobs. What's your take on the future of PM in in AI, if any?
00:24:25 · Lenny Rachitsky, Casey Winters
[00:24:25] S1: Mhmm. Well, I don't know. Another thought is there's this mean that g p t four is gonna... Or five or six or 10 is gonna replace product managers. And anytime some new feature comes out, people put out these videos of, oh, look. They're doing all the PM's jobs. What's your take on the future of PM in in AI, if any? [00:24:41] S0: Well, I think if you thought the PM job was just filling in the latest, you know, Reforge or Shreyas framework and then getting, you know, that automatic Thang promotion every year and a half [00:24:52] S1: Mhmm. [00:24:52] S0: Then, yeah, you're gonna get replaced by AI. But I think the real PM job is the least likely to get replaced over time because you need, you know, real subject matter expertise. You need to, you know, be trading off a lot of different types of things and and making good decisions for the company and and for your customers. So in terms of using AI now as a PM, I'd actually be cautious in, like, the current iteration of the cycle for PMs. Yep. It's a tool that's trained on sounding smart rather than always necessarily being smart. I was at Eventbrite the other day, and someone was telling me how they were loving the new Notion AI integration. And she asked me if I'd used it. I said, no. She's like, oh, you totally need to. Hey. Go ask you your bio. It's really cool. And I said, alright. Let's just do it on [00:25:39] S1: your screen.