Lenny's Podcast: Product | Career | Growth
00:14:17 · Lenny Rachitsky, Jessica Fain
[00:14:17] S1: Also former podcast guest. What a run we're on. [00:14:21] S0: Yeah. I've learned so much from Noah. We sat down to write product principles for Slack. And Ethan Eismann, our head of design, was leading that initiative, but really this was a lot about codifying the early ideas that made Slack great, especially from a product principles and sort of craft perspective. And we started talking about this and Noah had been at Slack early on, and he pulls out a small notebook that he kept in his bag and he said, "I actually have a section of this notebook that I've been keeping things I learned from Stewart over the years." Now, he hadn't been keeping that notebook because he said to himself, "Oh, one day we're going to write product principles, and I'm going to want these quotes on hand." Or, "I'm going to show off that I have this." No, it was for genuine learning and growth of his own ideas and place as a product leader that he was taking those. And what it allowed him to do was, reflect back to Stewart ideas and principles that he had, but also grow his own product sense intuition. And as an organization, it then allowed us to scale those principles, and I think was a really, really important part. And we worked with a lot of the sort of early Slack folks and the people that had really developed that culture, but it was folks who had really tried to grow and learn. They weren't trying to politic, they were trying to build great products. And that's the approach we have to take.
00:15:45 · Lenny Rachitsky, Jessica Fain
[00:15:45] S1: Okay. So what if you're not working for Stewart, which most people... Stewart also former podcast guests. I feel like just the alumni of Slack, holy moly, just like this is a... [00:15:55] S0: We had a really good run. [00:15:56] S1: The fact that, just the fact that I have so many of these people on the podcast, what a sign of an incredible team. Okay. So yeah, so most people do not work for a Stewart that has incredible product sense, really cares about craft. And most people are like, "He or she is so wrong about what we're doing, this is such a mistake. They don't listen, they don't know what they're talking about." How do you deal with that?
00:16:19 · Jessica Fain
[00:16:19] S0: One assumption I have of how folks may misunderstand this skill is that they have to be a yes man. They have to take everything that the leader said and do exactly that. That is absolutely wrong. You get paid to have an opinion, you get paid to be a domain expert. And in a lot of ways, your executive is looking for you to be the deepest person in the room, especially if they're good at their job, right? They're looking for you to be the expert. And so, bringing your expertise to bear is absolutely crucial. Ilan Frank, who was my boss at Slack as well, is now CPO of Checkr, he always had a customer anecdote in his back pocket. I can hear him in my head saying, "I was just on site last week with so-and-so and they said blah, blah, blah." He always brought his expertise to bear, and many of the executives at Slack were not from a strong enterprise background, so he could bring that to the forefront. I think that has to be married again with that curiosity and empathy. If you hear something that you don't agree with, this is something that a guy my team does super, super well right now. He'll hear something that flies in the face of the data he's seeing, the insights he's gotten, his experience in his domain expertise, and he'll say, "That's so interesting. What led you to believe that?" That kind of question is actually curious, about this person said something that I think is dumb, but there must be something behind it. And so if I actually care what's behind it, and what you end up doing in that question is co-creating with the person who offered the opinion in the first place. You're able to say to them, "I'm interested in what led you to that belief, your experience. Did you have a meeting last week? Are you getting pressure from the board right now in a certain way? What is leading you to that belief?" I think one thing that really trips people up is execs are so good at seeming certain. They say things in an authoritative way with confidence, with surety, because so much of their work is having to make those ultra-fast decisions with little information. But if this is someone who is also a learner, who also has a growth mindset, then if you are able to help them unpack why they believe something and then respond with your own domain expertise, you are able to get to a better solution together.
00:18:50 · Lenny Rachitsky
[00:18:50] S1: I love these very tactical phrases and tips for how to deal with someone, say a leader. Let's just say this is like they're a director of product, VP of product, CEO that you're trying to convince to agree to plan. So the phrase you're suggesting here is, "That's so interesting. What led you to believe that?" Anything else along these lines, say you're pitching a product or an idea to say a VP of product and they're just like, "Hmm. What else works?"
00:19:17 · Jessica Fain
[00:19:17] S0: The earlier that you can understand the belief system and the things that are important to them, the better off you're going to be. So very, very early on in this process, what is top of mind for them? I can count on one hand when I was chief of staff, how many people asked me for advice before going into a product review with our CPO or our other executive team to say, "What do you think is most important to them right now?" Use the people around them, their EA, their chief of staff, the people who have successfully pitched ideas in the past and say, "What worked? What do you think they're worried about? What are the risks?" And in an age of the tools of AI that we have, this is so much easier than it's ever been, right? You can ask Slackbot, "What has Rachel been posting about lately? What do you think is most important to her?" A colleague of mine, a peer on our product leadership team, trained at GPT on a bunch of transcripts from past product reviews that are all publicly available, and we expect that our PMs are running their PRDs or their pitches through that, to say, "What's Rachel going to push back on? Where are their weaknesses in these ideas?" You can also train things on, "Where are your own weaknesses? I know I've gotten feedback in the past that my data is a little thin or that this kind of UX thinking is thin. Give me feedback on that." Claude's amazing for this. And so, I think that the first step is actually just saying, what's important to them? What do they want to hear and anchor on that? I think the second piece is going in to learn not to convince. And the earlier on you do that, the better. So we have something at Webflow called Office Hours. As early as you can, you are having these conversations to align on strategic direction, maybe even before you have a one-pager. We implemented something at Slack with Stewart Butterfield, because we realized we were coming to him with done designs and he was like, "What the fuck is this? This is completely different than how I had this in my mind." So Ali Rayl, early Slack employee implemented something called, "Hey, Stewart Butterfield, what do you think?" And we would just sit with him for half an hour and say, "What do you think on this topic? What's your belief system? What's your past experience?" And we started with a user interview, right?
00:21:31 · Jessica Fain, Lenny Rachitsky
We started with, "We actually want to download your expertise here." And I think that when you engage execs in that way, it's really, really valuable. One of the things I see people do poorly is, they don't ask for the time. This is sort of in counterpoint to what we were talking about before with how busy their calendars are, but they're afraid to ask for more time to get that insight. But sometimes if you don't, you miss the point. [00:21:57] S1: Something that we hear a lot on this podcast, is as a product leader, as a leader of any kind, you want to have a point of view, you want to come into a discussion with, "Here's our options, here's what I think is the right solution." And then at the same time, as you're describing, you want to come across as, I want to learn. I'm not here to convince you. I'm here to just help understand your worldview and where you think the right path is. How do you think about just those two, that balance of, I have something I believe is right and, okay, but I'm here to learn and get your feedback and see what you think makes sense.