Lenny's Podcast: Product | Career | Growth
00:22:30 · Jessica Fain
[00:22:30] S0: Okay. So my advice on this may be a little paradoxical, because I think people make mistakes in both directions on the polls here. On the one hand, I think there's an error people make of trying to show too much work, trying to tell too much upfront proof point. We talked to 16 participants from these 15 GOs and this is the statistically significant and the exec is like, "I'm so bored, I'm going to die." I remember I did this in a review once and literally the person I was most trying to convince glazed over, got on their phone and I totally blew the meeting because I was trying to prove that I had done my homework. Put it in the appendix, right? They don't need to know every single detail. The baseline expectation is that you did your job, and that this is built on a solid foundation of your domain expertise. On the flip side, I think there's some balance of showing your work, that helps elucidate why your solution is best. So one of the mistakes I see people is doing is giving only one option. I think that people, if you say, I mean, this is also like classic pricing and packaging strategy, give three options and the Goldilocks in the middle is the perfect one, right? But I think that what that actually allows you to do is say, "Hey, we considered. We are not dumb. We did not miss something. You think we missed something, but no, no, no, we actually considered this." So we had a recent product review with my manager, Rachel Wolan, she was a recent guest on How I AI, and- ... she was a recent guest on How I AI, and we brought a doc, a sort of reasonable approach to what we thought was the sort of problem and strategic space we were going after. It didn't go well. It really didn't match her expectations. And the feedback she gave us, which was really, really the right feedback, was I don't understand how you're thinking about the permutations if possible here because we had only given one option set. And so what we did following that review is we said, "Hey, we really want to sort this out. We want to get moving. We want to show that we can really get building on this product. And alignment is the next stepping stone for that. Can you meet in two days?" And we turned around a new doc in two days that actually showed all of the options we had considered, but hadn't brought to that first review.
00:24:53 · Jessica Fain
And once we elucidated all the things we considered, and why we thought they would or wouldn't serve the outcomes we were driving and the technical complexity behind them, she was like, "Oh yeah, okay. I see why the solution that you're proposing makes the most sense for what we're trying to accomplish." But in the first version, in the first meeting, we hadn't shown that and we hadn't workshopped it through her. And so sometimes really tactically you want to have that available to you. It's not necessary to put all 15 options you considered, but at least be ready to show them. Have them in an appendix, have them in a draft Figma file, whatever it is. We used to have this rule after a design review with Stewart Butterfield. We'd go through the design review and he'd say, "No, do it exactly like this. I want the button here and the interaction to be this." And frankly, he always had better ideas than we did, but we would come back and we called it Stewart Butterfield plus two more. So we did exactly what he asked for and then two other versions that we felt good about. And then it gave us a forum for conversation to debate the merits of each type of approach.
00:26:06 · Lenny Rachitsky, Jessica Fain
[00:26:06] S1: Awesome. Okay. So there's a bunch of advice here. One is the default is don't go in with, here's our whole process that landed on this suggestion, but have that ready because they may ask for that if they don't buy into it. Another is present options. And then there's, here's my point of view, here's why I think this is the right one. And then if they dig in, you have to be ready for more options. Have you ever looked into the Minto Pyramid way of presenting stuff? [00:26:31] S0: No, I don't know what that is. [00:26:33] S1: Okay. So there's this lady Barbara Minto. She's like from the 50s, I think. She was the first female consultant at McKinsey or something like that. And she figured out the best way to present information to execs is backwards. Essentially, it's instead of here's our process, here's all the things we did, here's our set of conclusions, and then here's our recommendation. It's flip it, start with, here's our recommendation, and then here's the things we explored, and then here's the evidence behind that. It feels like that's what you're describing.
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?