Lenny's Podcast: Product | Career | Growth
00:07:25 · Lenny Rachitsky
[00:07:25] S1: Is there anything that you learned from that experience to to survive in that role for three years? You know, I imagine you have a lot of skills and you're very valuable to the company, but I don't know. Any... Someone that's in that role, maybe right now, just like, here's something that I did that maybe you should do.
00:07:40 · Casey Winters
[00:07:40] S0: The first one I can think of is a big change from being a product leader to a, you know, a CPO or or something equivalent is you're actually a comp exec first and a product exec second. So I think some mistakes I made, you know, early that I I corrected successfully is you wanna show that you are caring and paying attention to the overall business first before just taking care of your own, you know, product designers, product managers, researchers, whoever. So that's that's advice I found myself doling out to other product leaders a lot more now that have, you know, gone through it. You have to not only truly care, but create the perception that you care about sales, about marketing, about, you know, legal, etcetera. Because first and foremost, you're expected to leave the business, you know, at at that level. So I think that's something that I think is really important, and I think something else is really trying to diagnose without as much bias as possible where the strengths and weaknesses of your team, where the strengths and weaknesses of your product, lay that out with your peers and say, here's where we are, here's where I think we need to go, here's the timeline on which I'm gonna work to get us there. Because I think product's such a confusing, discipline for people who aren't in it, a sales leader, many CEOs, you know, marketing leader, that they don't necessarily know what great looks like. And the things they know about great leadership, they don't know if you know those things. So you have to make it really clear. Yeah. I know our OKRs are not as quantitative as they should be yet. That's because this team isn't ready for x, y, and z. This is where we're gonna get them to, but it's gonna take some time. So one of the things we did at Eventbrite that I thought was really helpful is, you know, when you go public, you tend to rotate over your executive team and get public company execs versus startup execs. So a few of us were new, and it's just like, hey. Let's do a deep dive on product. Let's do a deep dive on customer support. Where is it at right now? What do you feel like your job is? What do you feel like are the issues you're facing? Where do you wanna take it over the next three to five years? And then let's talk about it.
00:09:55 · Casey Winters, Lenny Rachitsky
And just forcing you to, like, write it all down is is really helpful, but then it forces you to explain it. And it helps the rest of the executive team get better company execs because, you know, now they really understand product a lot more deeply or understand finance a lot more deeply, whatever the function is. [00:10:15] S1: Speaking of, gaps and opportunities for people in the company to level up, you've kind of been, highlighting this trend that I thought was really interesting, something you call the zero interest rate phenomenon product manager. Can you talk about what that is and what you've been noticing?
00:10:32 · Casey Winters
[00:10:32] S0: Yeah. Sure thing. So this is something I started noticing while managing, you know, PMs and product designers at Eventbrite, and it's now coming up with, with Whatnot as I hire... Help them hire new PMs, is the environment in which a lot of product managers have come up is is very distorted from when you and I started doing this kind of work. I think we used to always describe PMs as, you know, this gang of misfits. We all started in different functions. We all had different strengths and weaknesses, and the PM team, you know, gained as a whole from that diversity of skills and and previous experiences. So what I noticed is when we started doing product reviews at Eventbrite, if there was any sort of, like, uncertainty in a problem or a solution, the product manager, instead of, like, shipping to learn, would talk about all this research they have to do to to really learn the problems, really learn the solution. You know? And and my feedback would be like, no. Like, we... You know, user research is a scarce resource. We have to reserve it for the areas that have extreme uncertainty and a high leverage for getting to certain. So if you're redesigning the login page for Eventbrite, you don't need to use that resource to learn what to do. Just go see what FAANG and the top unicorns did. They probably did a good job. And, you know, even if they didn't, all of our customers also use those products, so they're gonna be familiar with us copying any approach that they've taken. So I think we sort of forgot in the industry that many times the fastest way to learn is to ship. So then if you actually get them to skip research and just go look at competitors, another thing I was noticing is I get, like, a list of options other companies have done, but there would be no analysis of why those companies chose different options and what's, you know, most applicable, you know, for us. So it got me thinking, like, okay, every new person in the product team is acting like they work at Google and have these infinite resources and infinite time to make sure everything is perfect. And there became such this focus on the right way of doing product management that no one's taken any risk. And I felt like, oh, am I responsible for this? Like, I've created a bunch of, you know, frameworks on Reforge. You know, I'm onboarding these UPMs.
00:12:46 · Casey Winters
It's like, is this is this my fault? But, you know, you know, in Reforge, we're building frameworks that are tools in a in a toolkit. You pull them out when relevant. They're not a coloring book, you know, to stay, you know, inside the lines of. So at one point, I got so fed up. I wrote, like, an internal blog post, and I called it on best practices and breakfast rituals. And I talked about how there were these articles about the morning habits of the most successful people. And if you try to do all those things, it'd take you, like, six hours every morning. And there was this article, I think it was on Business Insider or something, about this futurist at Google, and he talked about all the pills and food heats for breakfast every morning to try to live longer. And the reporter estimated that it cost him 1,000,000 a year to have these habits. So I was like, hey. I wanna make it clear. At Eventbrite, we don't have that much money. We don't have that much time. There's no framework that allows you to not use your brain at this company and just follow some sort of process for success in in this profession. So I I adopted this thing into, like, a a public blog post that's on my blog now. But now that I've had some time outside of Eventbrite, I feel like I at least partially missed the mark on what's really going on. You know, I see this with, like, whatnot because one of the things I'm helping them with is interviewing ICPMs again, which I haven't, you know, done in a while. And it's fascinating interviewing a PM or managers early in their career because Whatnot is a startup. And and, you know, you know better than most of us as a former founder of one. Startups typically require us to wear lots of hats. You have to write SQL. You have to talk directly to customers. You have to prep marketing and sales. And most importantly, you have to make a lot of decisions under uncertainty, which you wouldn't necessarily expect a PM to do at, you know, say, at Google. But it all boils down to using your brain in different ways. You know, Lisa, who's on our legal team, she called Eventbrite a public startup because the pandemic basically erased her business, and we had to build it back from scratch.
00:14:52 · Casey Winters
So now that I'm doing these interviews, and whether they come from a small startup, a unicorn, or a public company, they all sort of look the same because there's been so much funding to all these companies. Every company's been acting like they're Google with Google margins, meaning a lot of engineering support, a lot of design support, a lot of research support, lots of analysts around them. And they actually seem pretty ill prepared for a real start up or even a public company with some uncertainty around it, like Eventbrite. So you start getting these weird responses in the interview process. You ask them to solve a problem, and they'd say things like, I can't even begin to come up with solutions until I see all the data and talk to customers. And I'm like, yeah. I get that that's something you would normally do if you took the job, but, like, you don't have the data. You can't talk to customers. Make a decision now. What would you do? I wanna see how creative you are. I wanna see how much you're intuiting about the real problem and solution, and they can't really answer. And then, you know, my follow-up, which I don't ask, but what I really wanna ask is like, so when's the last time you used your brain versus followed a process someone else designing your company? Because, like, I want the former, not the latter.