Lenny Rachitsky: evaluation

Transcript context

…Well, I think the best way to coach is actually to do it before the meeting, so I think there's a tendency in product management and product design to want to do meetings where there's kind of this big reveal and an aha to the audience. And it's kind of the opposite of how you want to handle most of these situations. You want to de-risk that meeting not make it a big success or fail moment, so there's a few things that I do. One is if there is a big presentation coming up or something like that, I try to run through it with the team, pretending to be the other members of the audience that are going to be there, so I'll say, okay, well, what the CFO's going to ask about here is X. And you want to answer that question before it gets asked. What Julia, our CEO is going to ask about is why, so you want to weave that into the early story and not wait for her to ask. You kind of role play the entire thing based on the different people that they're going to be communicating with. Something I commonly say is that executive communication is actually executives communication. You're communicating with individual executives that all have different styles and different concerns about the business or about the particular problem you're working on. And you want to anticipate that, and if you don't have enough experience say presenting to the CFO or the CEO, I as the chief product officer do, so I can impersonate them and help you understand what they're going to care most about. The other thing that I push a lot of my team to do is have pre-meetings with some of those key individuals, so that they're going to be less surprised in the meeting about what you're talking about, that you've gotten any major concerns brought to your attention before the big meeting. And that helps de-risk how poorly a meeting like that can go, so definitely at the individual presentation level, doing that pre-meeting. What I'm working on a lot now is trying to have more of a scaled approach to training this type of upward communication. And what types of frameworks, what types of structure tend to work for Eventbrite and making sure that everyone on my team is just really well versed in that and comfortable in it because of course, confidence projection is a key part of these types of meetings as well. This is such important advice that I think a lot of PMs don't recognize how important it is to prepare for important meetings like this. Just to give folks context, maybe that aren't doing this sort of thing when they're working at a larger company, how much time do you spend or an ICPM should spend on preparing for these things just to set a little bit of a reference point? Well, it's an interesting question because I think different people have different styles on how they want to handle this. I'd say the way my brain works in these situations which I think is a little bit atypical, is I'm actually a little bit better if I am free forming a lot of elements and just speaking from confidence in areas I know versus specifically trying to lay out every exact bullet point I want to hit. I'm going to show up as more comfortable, I'm going to show up as more dynamic, and I'm going to be able to engage in a more thoughtful conversation, so for me, my approach to these sorts of things is I write a lot. I write a lot of notes. I write a lot of documents. And then in general, for any of these types of communications, I am just pulling from things I know deeply because I've written them down, I've thought a lot about them. For a lot of other people they really just need to spend a lot of time on prep to make sure they nail the communication they want to nail. And I found it requires a different amount of investment for different people on my team, so the point is not as much how much time you spend, it's how well do you really know the material, and how well do you really know what your audience is going to care about with that material so that you are prepared for every question you might get. I'll give an example from my Pinterest days, the primary way with which you interfaced on any key strategic topic was product review, right? You'd go in and you talk to Ben, our CEO and Jack our head of product. And Ben and Jack had very different styles of communication. Jack in particular would very early on ask a few different data questions to get context on the problem. And if you, as a product leader or an individual PM or an individual designer didn't know the answers to any of those, it cast doubt on the entire rest of that meeting. Because, the team wouldn't be confident that you had all the right context to understand the problem, so a lot of what I would coach my team on is, okay, I'm pretty confident Jack's going to ask this question, then this question, then this question. Based on the material I'm seeing from you, how well are you prepared to answer those questions? Different execs might be somewhat different in that regard, but if you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present, you're not prepared enough, right. You need to know the entire universe of how that meeting can go. And that may take you dozens of hours, it might take you three hours, but the most important thing is that you've asked what possible questions can be asked and am I prepared to answer all of those? Do I have all the data in front of me to answer all of those? But because if I don't the chances of the meeting you're having a negative outcome just increased dramatically.…

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