Casey Winters: commitment

Transcript context

…Can you talk a bit about how you actually coach PMs on this? Is this like in one-on-ones you revisit a presentation they gave that could have been better? Is it after a presentation, you pull them aside and talk through what they could have done better. How do you approach that? 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?…

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