Lenny's Podcast: Product | Career | Growth
00:00:00 · Jessica Fain, Lenny Rachitsky
[00:00:00] S0: As product managers, one of our best sets of skills is curiosity and empathy and trying to understand our users. But the moment that we're talking to an executive, we forget those skills and those talents. [00:00:11] S1: It's your fault if the leaders didn't buy into your idea. [00:00:14] S0: People completely misunderstand how executives make decisions. What is going on in the head side? Describe an executive's calendar as a stroke light going off. You wake up at 8:00 AM, you've already got a huge list of urgent things going on. They have not had the time, the energy, the wherewithal to center your problems. [00:00:34] S1: What are their goals? What are they trying to do? How are they measured, connect the thing you're pitching them with that success? [00:00:39] S0: There's ways for us to ask much more interesting questions of our executives. Tell me what the board is pushing you on. Execs want to be successful too. They want to be good at their jobs. [00:00:50] S1: Sometimes you have the best idea and they just don't bite. [00:00:52] S0: One of the biggest things you can do to build trust is kill things, deprioritize things. 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 get paid to be a domain expert. Your executive is looking for you to be the deepest person in the room. Bringing your expertise to bear is absolutely crucial. You have to act like a CPO.
00:00:52 · Jessica Fain, Lenny Rachitsky
[00:00:52] S0: One of the biggest things you can do to build trust is kill things, deprioritize things. 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 get paid to be a domain expert. Your executive is looking for you to be the deepest person in the room. Bringing your expertise to bear is absolutely crucial. You have to act like a CPO. [00:01:17] S1: Today, my guest is Jessica Fain, who's been a product leader at Box and Slack and Brightwheel, and now at Webflow. And she has gotten very, very uniquely good at the art and science of influence, and in particular, influencing executives. Influence might be the single highest leverage skill for product leaders outside of AI. We actually get into how AI is changing the skill of influence. I've never heard a podcast conversation get deep into the art and science of influence, how to actually change people's minds, and the mistakes that people make when they're trying to influence leaders. We get very tactical and very specific. There's a bunch of stuff in this conversation that I've never heard before or thought about. I am very excited for you to learn from Jessica. Before we get into it, don't forget to check out lennysproductpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Now, let's get into it after a short word from our wonderful sponsors. [00:04:01] S0: Thanks for having me.
00:04:01 · Jessica Fain, Lenny Rachitsky
[00:04:01] S0: Thanks for having me. [00:04:02] S1: It's my pleasure. Let's set this conversation up. We're going to be talking about the skill and the art of influence, and in particular, influencing executives and leaders. People above you that you want to convince to do things you want them to do. Help us understand why this is worth people's time. Why is this worth the next hour of someone listening to this? Why is this skill so important to people's careers? [00:04:26] S0: I think as product builders, there's almost not a skill that's more important. Influence and building momentum behind great ideas is the way that great products actually get built. And if you don't have that influence, if you don't have the buy-in and the backing of your key stakeholders, of your executives, you can't build great products. [00:04:49] S1: Something that I personally went through is just like... I was in a period of like, I don't need to work on this skill. I'm just like, I'm just going to do amazing work. It's going to show itself, of everyone's going to recognize it. And everyone run into this wall of like, oh man, all these other people are getting promoted. Maybe talk about that because it feels like that's a big trap. People run into you.
00:05:09 · Jessica Fain, Lenny Rachitsky
[00:05:09] S0: I think why I wanted to talk to you about this is, when I was an ICPM, I was putting forth ideas. I was trying to reflect what I was hearing from my customers. I was trying to get sort of buy-in and excitement about the work that I thought was really going to move us forward. And at the time that I'm thinking about, I was a PM at Slack, and some of my ideas got people really excited, got me funding and backing, and just really a sense that we could accomplish something great. And some of my ideas and the things that I really, really believed in died on the vine. They went nowhere. And I was so confused and frustrated, honestly. Because I felt like, "Hey, I really get this user base. I really understand what's going to move the ball forward and I don't understand how these decisions are actually being made behind the scenes." And I was eight months pregnant, eight and a half months pregnant, April Underwood, who had just been named CPO of Slack. She had just come back from maternity leave. We had a two-day overlap and I sort of got up my courage and I said to her, "April, I've admired you for a long time. I love the way you work. I really love the way you think. And I really want to understand it better. If you'd ever consider having a chief of staff, I'd love for you to consider me." And when I came back from that maternity leave, I came into a stint as April's chief of staff and was later chief of staff to Tamar Yehoshua who succeeded April. [00:06:38] S1: Who has been on the podcast.
00:06:38 · Lenny Rachitsky, Jessica Fain
[00:06:38] S1: Who has been on the podcast. [00:06:39] S0: Who's been on the podcast, and is now a CPO and head of AI at Atlassian. Tamar, don't be mad if I mess up your title. And what I learned through that process is that people completely misunderstand how executives make decisions, what is going on in the heads, in the calendars, in the incentive structures of executives. And, instead of really understanding where that exec or stakeholder is coming from, they center themselves, they center their own desires, their own motivations, their own slice of the world. And they end up just not being as successful both in their career, but also in the types of products that they're building. [00:07:21] S1: What's an example of that when you talk about, people don't understand how product leaders actually make decisions, how they decide what to do, what to listen to, what's an example?
00:07:29 · Jessica Fain
[00:07:29] S0: Oh my gosh. I think the biggest example of this is people don't understand executive calendars. A lot of times on Google Calendar, it's blocked. You can't see what they're working on, but I describe an executive's calendar as like a strobe light going off. You wake up at 8:00 AM, you've already got a huge list of urgent things going on. You go from a meeting with finance on a budget, to an interview for another executive, to a people problem, to a legal problem, to a product review. And the product manager coming to that product review, or the leader who's trying to make a pitch, thinks, "I've been prepping for this meeting for two weeks, three weeks, maybe six weeks since we last spoke," but the executive coming into that session hasn't thought about you since. They may not have gone to the bathroom today, right? And you have to understand that they have not had the time, the energy, the wherewithal to center your problems and you have to help them get into that mindset. So this is as simple as, execs are people too, right? They are running around context switching in the most insane ways I've ever seen, and everything that comes across their plate is an emergency. So one of the biggest tactics I think is so important is, just take 30 seconds at the top of a meeting. Why are we here? What happened the last time we talked? Why is this important to you? Why is this meaningful? And really remember that they are not thinking just about you. They are optimizing for a global maximum and not for the local that you're optimizing for.