Lenny's Podcast: Product | Career | Growth
00:27:04 · Jessica Fain
[00:27:04] S0: Yeah. I think that's a really good way of doing it. I think my only gloss on that would be that people are really different. Execs are people too. And so one of the things that I think is really important is understanding what is the literal format, storytelling, pre-work that is going to work for that person. Some people hate a PowerPoint and it's just going to crush their soul if you start doing that. Some people only want to see the data and not the qualitative research. And so I do think it is about really understanding their communication style. And execs, if you're listening to this, it's really fucking helpful if you tell people, because you actually know what you like and don't like. And so just tell people, "I prefer a doc. I want no upfront explanation. I want 10 minutes of quiet reading time, and then we can come back together." That's a particularly effective means for very busy people and short meetings, and especially in remote work where presentations just don't work very well. Some execs are willing to do pre-read, some aren't. And I think you just have to be willing to accept that they are also human, and you're trying to give them the best shot at inculcating the information in the way that is meaningful to them.
00:28:23 · Lenny Rachitsky
[00:28:23] S1: So there's a bunch of tips here that I want to summarize for how to set yourself up for success. One is what you just described, which is just think about how do they respond best? What kind of setup do they respond best to? Is it a presentation? Is it a here's what we recommend, here's three options. Is it data, something else? So there's just understand, here's what this person likes. They want a five minutes fast conclusion. Why? Then there's your advice of ask people that know them, what is top of mind for them right now? Because they may be like, "This is the big bet we're making right now. If it's not aligned with that, they're not going to care." So it's like either ask them or ask people around them, what's top of mind for them right now. And then there's this idea of simulate almost, simulate them, feed all the previous meetings with them into say a Claude project or something like that, create a little GPT and run your idea by them. And like, what would you say?
00:29:22 · Jessica Fain
[00:29:22] S0: I will tell you, I am not a big fan of the what's top of mind for you question. This is a hot take because I think that what often people do is they think through their top priorities, their top experiences. If we were trying to do a research study to understand the day-to-day lives of our users, we probably wouldn't say what's top of mind for you. We'd say, "Tell me how you spent your day." We'd say, "What's the most urgent priority for you right now that you're really scared about messing up? What pressures are you facing?" And so I think there's ways for us to ask much more interesting questions of our executives. I recently did this with our CEO. I said, "Tell me what the board is pushing you on because everyone's got a boss. And even a CEO who seems so powerful and competent and sure is getting pressures, right? What are you seeing as the key inputs to your success?" The other thing people don't realize is execs want to be successful too. They want to be good at their jobs. And how can you help them? In the best case scenario, your incentives at a local team level or product organization level really closely align with their incentives that you're working on something that really matters to the company. If you're not, you really should be having that conversation because you'll be in misalignment from the start. But if you actually have alignment, point out that alignment. How is the metric that they're trying to move, the OKR they're responsible for, the board pressure that they're under going to be improved by the thing that you are proposing and how do you get there together? So I think that one of the things people really miss out on here is what are the success criteria for an exec? And how do you model your world to amplify that success so that both of you can be more successful?
00:31:25 · Lenny Rachitsky, Jessica Fain
[00:31:25] S1: Okay. And that is such an important lesson before I follow that thread. Just to clarify this question of what is top of mind, your advice was ask people around them, what is top of mind for them? Don't ask them directly this question. [00:31:37] S0: Top of mind has become this sort of trope, right? It's execs write a weekly writeup of what's top of mind. And it becomes this generic, uninteresting, neutralized frame. And so I think the question, what's top of mind for you has actually lost some of its firepower. And instead, we have to get at what is the emotion, the drive behind it, and what's the spicier question that'll get a more interesting answer. [00:32:11] S1: So then going back to this incentives piece, such a powerful lever for basically to get anyone to agree to what you want, which is what are their goals? What are they trying to do? How are they measured? How is the success for them? And then how's the thing you're pitching them aligning with that and will help them achieve that specific goal?
00:32:33 · Jessica Fain
[00:32:33] S0: And in building products together, your incentives should be making your users successful, making your business successful because of that. And so what do they actually believe about that? It's not just about, oh, they want a promotion or they don't want to get fired or they want to hit their KR. Those are very, very real human things. But in an ideal world, in product work, it is really based on building incredible products for your users and therefore great outcomes for your business. And so I think a big part of this is actually understanding their strategic insights and what they believe is going to move the business forward most effectively. So after I was chief of staff, I took over Slack's core product team. We worked on channels and emoji and search and messaging. And there was a real feeling from our executive team that we had a bit lost our mojo around product craft. And we talked about painting the insides of the cabinets. We really wanted such an amazing experience for our users. That was one of the things that made Slack great in the first place was just it really felt like a product that took that usability to a 10X place. And there was a sense that I had heard from our leadership that we weren't quite there, and we had lost some of that. And that was so, so important to who we were and how we showed up for our users. And so we implemented something called the customer love sprint. We said, "Okay, engineering, stop what you're doing. As an entire team, we're going to spend two weeks just painting the inside of the cabinets." The only rule was engineers got to pick what they worked on. We supported them from a PM and design and customer support perspective. We gave them tons of ideas that engineers could pick what they worked on. The only rule was that you had to ship something. You had to ship something that was good for users. And what we did is you could call this a bugbash. You could say, "Okay, you got to fix these rough edges, these misses in the product." But we made it a huge deal. We made it really exciting and fun, and we had a big, really fun judging competition that our executives took part of. And we really brought back that part of our culture that we had lost out on a bit.
00:34:53 · Jessica Fain, Lenny Rachitsky
And it spoke to what our executives believed was a differentiation for us and how we were going to show up in the market, show up to our users, grow our user base by making it feel special. And we were able to say, "Oh, we shipped 65 improvements this week, this sprint." And that felt really, really aligned with what they were trying to accomplish from a company perspective as well. [00:35:18] S1: Okay. So to summarize the tactics so far, one is align your pitch with the person you're trying to pitch is incentives. I don't know if the grammar on that sentence works, but what does success look like for them? Connect the thing you're pitching them with that success.