Lenny's Podcast: Product | Career | Growth
01:01:13 · Lenny Rachitsky, Jessica Fain
[01:01:13] S1: That is such a good one because everyone's always just trying to acquire more resources, more investment, just like more features and showing that, "Okay, this is a terrible idea. I know I spent months on this, but no, we should kill this because it's not working." [01:01:26] S0: Right. It's not working. And here's how I'm going to know that it's not working. Here's when I'm going to come back to you with a decision. So sometimes we don't know that. Well, a lot of times we don't know the outcome, especially with AI native products. And if we can say, "We're going to test this. Here's how we're going to know it's working. We'll come back to you on X date." I think one thing that really spirals people out of control is a desire for certainty. As human beings, many of us have a huge desire for certainty. Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now. I don't know if this is going to be successful. I'm going to check in with you on X date. That's when we're going to come back and have another conversation." And so at least there's certainty about the next check-in point, and that can be a really powerful tool for deescalating the fears and risks around a given initiative or idea.
01:01:26 · Jessica Fain, Lenny Rachitsky
[01:01:26] S0: Right. It's not working. And here's how I'm going to know that it's not working. Here's when I'm going to come back to you with a decision. So sometimes we don't know that. Well, a lot of times we don't know the outcome, especially with AI native products. And if we can say, "We're going to test this. Here's how we're going to know it's working. We'll come back to you on X date." I think one thing that really spirals people out of control is a desire for certainty. As human beings, many of us have a huge desire for certainty. Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now. I don't know if this is going to be successful. I'm going to check in with you on X date. That's when we're going to come back and have another conversation." And so at least there's certainty about the next check-in point, and that can be a really powerful tool for deescalating the fears and risks around a given initiative or idea. [01:02:28] S1: Okay. Before we get into AI's impact and all this stuff, are there any other common mistakes people make when they are trying to get better at the skill of influence or just any other really powerful tactics for increasing your ability to influence leaders?
01:02:28 · Lenny Rachitsky, Jessica Fain
[01:02:28] S1: Okay. Before we get into AI's impact and all this stuff, are there any other common mistakes people make when they are trying to get better at the skill of influence or just any other really powerful tactics for increasing your ability to influence leaders? [01:02:45] S0: Something people miss is the extremely broad context that execs bring to bear from not only their experiences, but the things that they are hearing in their day-to-day life. They understand what other product teams are working on better than you. They understand the conversation at the e-staff level. They've been to executive round tables and [inaudible 01:03:08]. And one of your jobs is to extract that insight and information and apply it to your ideas. And they want to feel like you care, like you respect that, like you can apply it to your own thinking. And so this keeps coming back to that curiosity and empathy. What do they know that you don't, that you can actually apply to strengthen your thinking or inform the direction that you want to take your team? And I think people just often don't ask those things of their executives. They don't show a curiosity for the expertise that that person has brought to bear. And frankly, I think often they don't really care, which is the chief mistake. They should really actually take it into account to strengthen their own thinking.
01:03:59 · Lenny Rachitsky
[01:03:59] S1: Yeah. So much of this is about just coming into it with like, here's what I ... It's just like having the same information. And I think there's a point about just believe they know what they're doing is so underappreciated. There's a reason they're in this role. There's a reason you're not there. There's a reason this company's doing as well as it is. And even if they are wrong, they believe they're right. So it's important to understand what they think and know and what information they have access to.
01:04:27 · Jessica Fain
[01:04:27] S0: Yeah. And I think the other piece of this is for anyone thinking about how they grow their career, how did that person get into the role that they are in? They broadened their context. They saw, sort of had great peripheral vision, and that is a way to show up in a room that is much more senior than you are, is keep your domain expertise, keep the things that you know best, but broaden your perspective, broaden your vantage point to think about it in the context of the whole ecosystem, the whole organization, the whole industry, which you often don't get a chance to stay in. And what happens at that point is you get seen as a strategic thinker. You get seen as somebody who really cares about the company's success and not just your own. And so it is actually a really, really important tool for growth, especially ... I had told April when I originally pitched her on being our chief of staff that I wanted to take the job because I wanted to know if I wanted to be a CPO when I grew up. And it's true. I still don't know because it's a really, really hard job and I have just way more respect than I ever did before that. But I think that if you want to grow into a product leadership role, expanding your viewpoint, expanding the way that you see problems, and thinking about it from a global perspective is a way to show up as that strategic leader that you say you want to be.
01:05:58 · Lenny Rachitsky, Jessica Fain
[01:05:58] S1: I love this advice. Just to make it very clear for people, because it's easy to just like, "Yeah, okay, I'll just expand my horizon," basically, the advice here is just think on behalf of the entire business, not just your feature, not just your little goal. It's like, what is the business trying to do? Here's how this fits into it. Here's what the CEO broadly is thinking about. The epitome of this to me is Jeff Weinstein, I think is how you pronounce his last name, or Weinstein, at Stripe. He's just like a PM on a product and he's just constantly tweeting and sharing Stripe as a business. He's just thinking about Stripe as the company and then here's this thing I work on that helps the company. [01:06:40] S0: Absolutely. And Jeff and I worked together at Box. [01:06:43] S1: Oh, you did? Oh, that is so cool. [01:06:43] S0: Yeah. [01:06:44] S1: Okay. So would you agree he's like the epitome of this?