Lenny's Podcast: Product | Career | Growth
00:32:33 · Jessica Fain
[00:32:33] S0: And in building products together, your incentives should be making your users successful, making your business successful because of that. And so what do they actually believe about that? It's not just about, oh, they want a promotion or they don't want to get fired or they want to hit their KR. Those are very, very real human things. But in an ideal world, in product work, it is really based on building incredible products for your users and therefore great outcomes for your business. And so I think a big part of this is actually understanding their strategic insights and what they believe is going to move the business forward most effectively. So after I was chief of staff, I took over Slack's core product team. We worked on channels and emoji and search and messaging. And there was a real feeling from our executive team that we had a bit lost our mojo around product craft. And we talked about painting the insides of the cabinets. We really wanted such an amazing experience for our users. That was one of the things that made Slack great in the first place was just it really felt like a product that took that usability to a 10X place. And there was a sense that I had heard from our leadership that we weren't quite there, and we had lost some of that. And that was so, so important to who we were and how we showed up for our users. And so we implemented something called the customer love sprint. We said, "Okay, engineering, stop what you're doing. As an entire team, we're going to spend two weeks just painting the inside of the cabinets." The only rule was engineers got to pick what they worked on. We supported them from a PM and design and customer support perspective. We gave them tons of ideas that engineers could pick what they worked on. The only rule was that you had to ship something. You had to ship something that was good for users. And what we did is you could call this a bugbash. You could say, "Okay, you got to fix these rough edges, these misses in the product." But we made it a huge deal. We made it really exciting and fun, and we had a big, really fun judging competition that our executives took part of. And we really brought back that part of our culture that we had lost out on a bit.
00:34:53 · Jessica Fain, Lenny Rachitsky
And it spoke to what our executives believed was a differentiation for us and how we were going to show up in the market, show up to our users, grow our user base by making it feel special. And we were able to say, "Oh, we shipped 65 improvements this week, this sprint." And that felt really, really aligned with what they were trying to accomplish from a company perspective as well. [00:35:18] S1: Okay. So to summarize the tactics so far, one is align your pitch with the person you're trying to pitch is incentives. I don't know if the grammar on that sentence works, but what does success look like for them? Connect the thing you're pitching them with that success.
00:35:18 · Lenny Rachitsky, Jessica Fain
[00:35:18] S1: Okay. So to summarize the tactics so far, one is align your pitch with the person you're trying to pitch is incentives. I don't know if the grammar on that sentence works, but what does success look like for them? Connect the thing you're pitching them with that success. [00:35:37] S0: Yeah. I think that aligning your incentives is, yes, really, really important in a product pitch. If you're thinking about a product pitch, how does it connect to the company goals? Are you trying to improve conversion rates? Are you trying to grow enterprise customers? Are you trying to be perceived in brand? Are you trying to break into some new category? Of course, you have to align on a new pitch. I think the inverse of this is how do you use that incentive structure to also inform regular roadmap, not just net new product ideas or net new pitches, but you're actually imbuing your entire team and your thought process with that incentive structure. It's a deep understanding. How did the OKRs get to be the way they are? How did the positioning statement get to be that way? How do I understand that and deeply embed it into my team's culture, so that we're reflecting what our exec team, our leadership has said is important? [00:36:35] S1: So basically everything should feel like it's a cohesive set of priorities based on some outcome y'all agreed to in the mission.
00:36:35 · Lenny Rachitsky, Jessica Fain
[00:36:35] S1: So basically everything should feel like it's a cohesive set of priorities based on some outcome y'all agreed to in the mission. [00:36:43] S0: Yeah. And I think a big part of this is also metrics and data and what you're actually measuring your own teams on. We talk a lot about leading and lagging indicators. Or in the nonprofit world, this is called theory of change. There are many steps. You yourself and your individual team may not be able to directly move enterprise revenue or directly move conversion rate, but you believe, and the company has a belief, that painting the inside of the cabinets, having an exceptional customer experience will be the thing that leads to customer retention, customer conversion, user satisfaction. And so how do you make sure that your metrics and the things that you are proposing to actually shift ladder up really, really clearly to those and that your executive agrees to that? [00:37:34] S1: Okay. And then a second lever is trying to not go into a conversation, even though you are trying to influence them. It's to go into it with an open mind and a learning mindset. You use this phrase. That's so interesting. What led you to believe that?
00:37:50 · Jessica Fain
[00:37:50] S0: Right. And I think in that is a disarming of the executive. Again, going back to how do you get the best out of them? You want them to feel comfortable. You want them to feel like they can be honest with you. I think something I see people miss often is they don't follow the subtle threads that executives lead them, the sort of breadcrumbs of opinions. In a more clear cut scenario, your leader, your executive will say to you, "Okay, I'd like a brief on exactly this thing. Write it generally this way. Let's review it in a week." That's a very clear cut ask. But very, very often the asks are more subtle. I wonder if I'm thinking about, have you considered? And what I find is that people don't take the bait. And the best people do. So I'll give you an example. Just last week, we've been working a lot on as skills get democratized across Webflow, everyone can do design, everyone can ship code, everyone can write a PRD. How are we enabling people to move as fast as their brains and tools will make them? Rachel, our CPO said, "Hey, Kev." Our head of design, "We're going to have to think about design reviews at some point." And within an hour, Kev had had a loom put together of, "Hey, here's a framework of high risk design changes, low risk design changes, blast radius, release processes, and how we might allow anyone in the organization to have designs shipped to production." That was a thread. She didn't ask him to do that. He didn't need to follow up in that timeframe, but he recognized that the organization's incentives are to keep empowering people, to keep everyone moving fast, to keep everyone really excited about what they're building as well. And he knew that he could slot in and respond to this feedback really, really quickly. A lot of times I see people don't take that invitation from the executive to actually engage on the subtle feedback they're giving. An example from my past where this didn't go as well was we were in a strategy review, sort of a quarterly strategy review, and it was probably the fourth time I had heard Tamar ask, "I'm interested in seeing the top 10 use cases on X." And the fourth time it happened, she got really frustrated. She said, "We've talked about this so many times before.
00:40:14 · Jessica Fain, Lenny Rachitsky
Why don't we have this documented?" And I think it's because people are not picking up on the cue that there's really something deep underneath. There's really an important piece of feedback or a question that they're not pulling on. Maybe you think that that's not an important thing to do, and then you need more information about why they think it's important. Because if you just let it go and you don't respond to the feedback or respond to the ask, that person loses faith in you, that you're going to follow up on a thing that they believe is important. [00:40:51] S1: And it also sounds like a really good way to influence is you take the reins and here's where I think we could go with this, and here's the answer to your question. [00:41:00] S0: Absolutely. I think if you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset? You have to act like a CPO. You have to come in with that perspective. You have to come in with a solution. You have to follow the thread that they've asked about. You have to do it quickly. One of the missteps here is people treat these interactions as so high stakes. And sometimes they are, but one of the ways that you fail at that interaction is you wait too long to engage on the feedback. If you wait a week for the follow-up items that you discussed in the meeting, that exec has moved on. And you've missed your chance to actually respond to the feedback in a quick manner, you will get so much more excitement, enthusiasm, brain power from them if you keep the ball rolling in a timely manner.