Lenny's Podcast: Product | Career | Growth
00:54:43 · Jessica Fain, Lenny Rachitsky
[00:54:43] S0: I'm thinking about a tool April Underwood taught me. She said she used to go into product strategy meetings with Stewart and was really trying to extract some of his ideas, but she was always holding the whiteboard marker. And so there was this back and forth between them in the conversation of, I'm trying to understand deeply what you're seeing in the market, what you're feeling in the business, what your instincts are, but I'm also going to package that in a way that is translatable, is actionable, is in a framework that you might not have had in your head. And so that is like a great tool for marrying that leader's instincts with your ability to sort of not synthesize their approach, but really take that approach and accelerate it for marrying what you know about the world and what they know about the world. [00:55:41] S1: So what I'm hearing is take it upon yourself to help them to kind of align your world view with their world view. And there's this question coming back just like, "Help me understand what I don't ... What was the question you had? Oh, that's so interesting. What led you to believe that?" These are the kind of questions that help you extract what you don't know that they know.
00:55:41 · Lenny Rachitsky, Jessica Fain
[00:55:41] S1: So what I'm hearing is take it upon yourself to help them to kind of align your world view with their world view. And there's this question coming back just like, "Help me understand what I don't ... What was the question you had? Oh, that's so interesting. What led you to believe that?" These are the kind of questions that help you extract what you don't know that they know. [00:56:01] S0: Yes. And I think there are also really different phases of a relationship. There's a phase when you're new, you may not have so much face time with that person, you don't really know them that well, but I think that this is a place where time spent together really just accelerates your trust with them, your ability to speak freely, to ask difficult questions, to get real feedback. And so especially if you're in a position where you can ask for that time, more casual time, less fraught, that you're not always pitching an idea, but you can have real conversations, that is also the groundwork for the pitch down the line. I think people devalue that, that time upfront spent together, because it pays dividends for the later pitch.
00:56:01 · Jessica Fain, Lenny Rachitsky
[00:56:01] S0: Yes. And I think there are also really different phases of a relationship. There's a phase when you're new, you may not have so much face time with that person, you don't really know them that well, but I think that this is a place where time spent together really just accelerates your trust with them, your ability to speak freely, to ask difficult questions, to get real feedback. And so especially if you're in a position where you can ask for that time, more casual time, less fraught, that you're not always pitching an idea, but you can have real conversations, that is also the groundwork for the pitch down the line. I think people devalue that, that time upfront spent together, because it pays dividends for the later pitch. [00:56:48] S1: Yeah. I'm glad you went there. That's exactly where I was going to actually go is this idea of trust and building and giving the person a reason to assume that you know what you're doing. Obviously hard to build trust. And the reason I think this is important is sometimes you have the best idea and they just don't buy it because they just don't know anything about ... They don't know what you've been up to. They don't know how awesome you are, how smart you are, how successful you've been your whole life and career, maybe because you're new. What are some tips for trying to build trust with the leaders so that these things become easier?
00:57:20 · Jessica Fain
[00:57:20] S0: I think in terms of building trust, it's really important to ground yourself in what they believe. If you are pitching an idea that is wildly different than something they believe, don't bother. You probably have nine other good ideas that are more aligned with the beliefs that they already hold. Follow those instead. So there's something about just engaging from a baseline assumption. If they feel strongly about something, okay, maybe you can come back to them once or twice and say, "Are you sure you feel strongly about that? I really see this data." And if they say, "Yeah, I feel really strongly," you probably have to drop it. But in terms of building that long-term trust, I think the biggest things that do that are really hearing them out and actioning on the feedback that you've gotten in the past. Having results. It cannot be overstated that impact in the organization, building great products, shipping amazing things quickly, feeding that back to the leader to say, "Hey, we worked with you on this. We shipped it. It went well. Here's the results." That builds you momentum to be able to go back with the more novel approach or the scarier one. I think the other thing I would say is one of my favorite ... Well, actually one of the only business books I've ever liked is called Switch. It's about change management, and they talk a lot about shrinking the change, which is this brilliant idea. If something seems scary and overwhelming, how do you make it so much smaller so that it's an experiment? It's a one week proof of concept. It's something that feels really small that can get people over the hump of, "Well, I'm not going to invest in six months for this project if I don't know if it's going to work." So shrinking the change is a huge way to build momentum and trust. And I think this applies to the way that we develop all products, especially if you're doing something that lasts longer than a month. What are your milestones? What are the chunks at which you're showing outcomes and fit? And this is easier than ever to do with the tools that we have at our disposal. How are we showing that we are taking a much more iterative approach so that you can build that momentum, build that buy-in, and get that trust to do the bigger thing?
00:59:36 · Lenny Rachitsky, Jessica Fain
[00:59:36] S1: That's an awesome, very tactical piece of advice here to convince someone to do something, is just reduce the risk essentially, reduce the investment to help build trust in, okay, this is showing success because obviously it's much easier to bite off on something that's going to take two weeks or- [00:59:52] S0: Absolutely. [00:59:52] S1: ... have a very low risk and impact if it's not a good idea.
00:59:52 · Lenny Rachitsky, Jessica Fain
[00:59:52] S1: ... have a very low risk and impact if it's not a good idea. [00:59:55] S0: Yeah, I think that's absolutely right. And I think what is the type of risk that they are most afraid of too? Is it wasting time? Is it time to market? Is it that they don't actually think this is going to work with customers? So if you can start to, and you can and should ask this, what are the outcomes you're most afraid of? What would a failure state be for you in this experiment? There's a concept of red teaming, which is originally a military tactic and now being applied to businesses. How do you take an outsider's perspective to your idea and not just be so obsessed with your own thinking, with your own concept? Because so often we get wrapped around the axle, especially ... I actually find this happens even more with prototyping. You build a prototype and you're like, "Oh, it looks so beautiful. I would've never been able to build that before." It's actually not a very good idea, but you get obsessed with it and you're unwilling to accept that it could fail. I think one of the biggest things you can do to build trust is kill things, deprioritize things. That is a very, very senior way of thinking, and it shows that you have the same aligned incentives as the executive who's thinking about the good of the company outcome, the user outcome, and not just your own.