Lenny's Podcast: Product | Career | Growth
00:51:31 · Jessica Fain, Lenny Rachitsky
[00:51:31] S0: Yeah, absolutely. This is going to be our new big bet. And this comes back to aligning with what the company's trying to accomplish and also the urgency. So some things, if you added a dozen more people or perfect alignment with go to-market, yeah, you could get them to market faster. But is that the most important thing for the company goals? Is right now the answer? Is accelerating this in this way actually going to do more? Or is it something else that's actually more aligned? And so I think it's still being so rooted in the company goals and what the exec is trying to accomplish and what your users really need to be successful so that you can say, "In order to accelerate our goals, here's what we can do." [00:52:13] S1: Like if you were in charge of a company, you'd be so excited if someone came to you with a 10X idea that's going to change the trajectory of your product. That's what everybody wants. And so that is a really powerful way of approaching all these things. Obviously not every idea is going to be a big idea. Not every idea is a great idea. A lot of times these take time also. Maybe speak to that. Just like say you have a big idea and they're like, "Nah," what are some expectations to set for people that come up with a big idea that just isn't getting any traction?
00:52:47 · Jessica Fain
[00:52:47] S0: It really depends on what kind of organization you're working in. If you're working in a smaller organization, if that big idea is something that you can build on your own or you can build within, versus if you need a large scale investment ... I think the real thing about building toward a big idea, towards something net new, the key is really outside and around the executive. So if the executive is the decision maker on whether we're going to invest here, they also want to understand from their peers, from other experts, why this actually matters. If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates, or the marketing team thinks that signups would be 10X because of this, if you have that cross-functional alignment, and this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but that if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf, I think that we now have more tools than ever to, as product folks, build out the V1, prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in to the point that the exec can't say no to the funding.
00:54:19 · Lenny Rachitsky, Jessica Fain
[00:54:19] S1: Along those lines, it feels like to me, the biggest reason that a leader doesn't buy into your pitch is you just have different information. They don't see what you see, you don't see what they see. They have all this other stuff that they're looking at and trying to decide. Maybe speak to just that skill of trying to clarify information on both sides. [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.
00:54:43 · 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?