Lenny's Podcast: Product | Career | Growth
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.
00:09:06 · Lenny Rachitsky, Jessica Fain
[00:09:06] S1: Essentially, this is how to help someone in this world that is running around from meeting to meeting without context on most things, maybe hasn't have time to go to the bathroom. How do we help them see what you want them to see, and maybe buy into your vision and suggestions? [00:09:21] S0: Yeah. I think that one of the ways that I phrase this is, how do you get the best out of your exec? How do you help them be their best selves? We often think about how we show up in a meeting, or the doc that we wrote, or the prototype that we've got ready, but we don't think about how they can be at their best. How do we give them the right kind of information in the way that they communicate? We as product leaders have to be communication chameleons. We have to be speaking their language, like love languages, but appropriate for work. And you have to think about, do they really turn a spark with a design, with a customer story, with a dashboard, with an experiment? And how do you understand how their best brain, how their best expertise, gets turned on to give you the best of themselves? But part of that is literally just setting up the meeting effectively, so that they can have the context, the wherewithal, the sort of breadth at the beginning of the meeting, to dive into it.
00:09:21 · Jessica Fain, Lenny Rachitsky
[00:09:21] S0: Yeah. I think that one of the ways that I phrase this is, how do you get the best out of your exec? How do you help them be their best selves? We often think about how we show up in a meeting, or the doc that we wrote, or the prototype that we've got ready, but we don't think about how they can be at their best. How do we give them the right kind of information in the way that they communicate? We as product leaders have to be communication chameleons. We have to be speaking their language, like love languages, but appropriate for work. And you have to think about, do they really turn a spark with a design, with a customer story, with a dashboard, with an experiment? And how do you understand how their best brain, how their best expertise, gets turned on to give you the best of themselves? But part of that is literally just setting up the meeting effectively, so that they can have the context, the wherewithal, the sort of breadth at the beginning of the meeting, to dive into it. [00:10:23] S1: The other thing I always tell people I managed is, it's your fault if the leaders didn't buy into your idea. You can't just be like, "Ah, they just don't see it. It's not my fault." They agreed to do something else. I always tell them, "That's just you're not able to influence them and convince them that you're right." [00:10:40] S0: Yeah. And Annie Pearl, who was my first PM manager back at Box. [00:10:47] S1: Also former podcast guest.
00:10:48 · Jessica Fain
[00:10:48] S0: Also former podcast guest, former CPO at Calendly and Glassdoor and now at Microsoft, and Annie's just the best. She always said to me, "It's not my fault, but it is my problem." And I think that that's the vantage point that a product leader has to have, especially if they're trying to put themselves in the shoes of an executive. 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 or to a stakeholder, we forget those skills and those talents, and we begin to think about our ideas, getting that approval, getting to the next meeting, whatever it might be, the incentive that we are driving. We don't think about the curiosity and empathy for what they're thinking about, for what their incentives are, for how their day has been. And, if we can take some of those skills of building great products and think about our executive as our key user here, then we can have a much, much more productive conversation. I think one of the most disastrous things you can do is going into a meeting just looking for approval for your plan. Instead, if what you go in with is, how can I learn? How can I strengthen this plan? How can I use the domain expertise, the context, the experience that this person brings to the table, and imbue that into my product work? Both the executive will like you better, because they will feel like you have actually built product alongside them. But, you will also end up with a better product. I often hear people say to me, "Oh, they just don't get it. They don't see what I see. They're not in my meetings. They don't know how hard this is." Fine. If you don't respect that person, if you don't believe they know something you don't, you need to quit. You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to the place that they're at because they learned and they developed a skill that you're trying to gain, awesome. Take the feedback, take the insight, ask questions, and don't just treat it like a rubber stamp, because that's a failure state, and it's a failure state that they don't like.
00:13:00 · Lenny Rachitsky, Jessica Fain
[00:13:00] S1: I want to dive deeper into this stuff, but first, something on my mind is some people might be turned off by this topic in terms of, it may feel icky of just like, "Oh, I don't want to try to be this manipulative person, and deal with politics and influence. I just want to do awesome work. Why do I have to do this?" Speak to that person that's kind of just feels icky about building this and working on this and being this person. [00:13:24] S0: Yeah. I think that when people frame this as politics, they're completely missing the point. Politics is manipulating outcomes and people for your own gain. Influence is about increasing the odds that your good ideas survive. And I think what happens is people actually let ego and let their own narrative, their own scope of influence, get in the way of empathy. So, this isn't politicking, this is learning. If we treat our stakeholder conversations as discovery interviews as a way to strengthen our ideas, then we end up in a much, much better place. And if we do that in a genuine and low ego way, I'll give an example here. Noah Weiss, who succeeded Tamar Yehoshua, CPO of Slack and also former podcast guest. [00:14:17] S1: Also former podcast guest. What a run we're on.