Lenny Rachitsky: uncertainty

Transcript context

…Yeah, I would say I still believe those things I said. It was funny. A product leader who will remain nameless emailed me when I hit year three at Eventbrite, and they said, "Congrats. You didn't get fired after two years. What's your secret?" I think it's very hard to keep product-market fit as a CPO within a company for a long time. The needs of the business shift over time, and of course, we all have different strengths and weaknesses in our game. No one's perfect at everything. In general, as an executive, it's just impossible to do everything perfectly, and any little misstep, mistake, or something you just missed can blow up in a major way. Frequently, CEOs have visions that can change and get misaligned with the product leader. Also, with leadership roles, you don't get put on a PIP. If a CEO loses confidence, it's over immediately. Nothing like that happened at Eventbrite. I started to see that the areas of leverage for a product leader were just less in my wheelhouse over time. I just talked to my boss about it, and we worked out something where I continue to advise on the things that I'm uniquely good at, and find other people who are better at some of these other things that were maybe more important at the time. Yeah, I'd say it's a really hard role, or a really challenging role. It can be a lot of fun. I learned a lot from doing it, but yeah, I still believe, and I think I've still yet to hear someone say they've really crushed it. Is there anything that you learned from that experience to have survived in that role for three years? I imagine you have a lot of skills and you were very valuable to the company, but I don't know, for someone in that's role maybe right now, just like, "Here's something that I did that maybe you should do. " The first one I can think of is a big change from being a product leader to a CPO or something equivalent is you're actually a company exec first and a product exec second. I think some mistakes I made early that I corrected successfully is you want to show that you are caring and paying attention to the overall business first before just taking care of your own product designers, product managers, researchers, whoever. That's advice I found myself doling out to other product leaders a lot more now that I've gone through it. You have to not only truly care, but create the perception that you care about sales, about marketing, about legal, et cetera. Because first and foremost, you're expected to lead the business at that level, so I think that's something that I think is really important. I think something else is really trying to diagnose, without as much bias as possible, where are the strengths and weaknesses of your team? Where are 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 going to work to get us there." Because I think product's such a confusing discipline for people who aren't in it, like a sales leader, many CEOs, a marketing leader, that they don't necessarily know what great looks like. 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 going to get them to, but it's going to take some time." One of the things we did at Eventbrite that I thought was really helpful is, when you go public, you tend to rotate over your executive team and get public company execs versus startup execs. 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's 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 want to take it over the next three to five years? Then, let's talk about it." Just forcing you to write it all down is really helpful, but then it forces you to explain it. It helps the rest of the executive team get better company execs because now they really understand product a lot more deeply, or understand finance a lot more deeply, whatever the function is.…

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