Lenny's Podcast: Product | Career | Growth
00:37:50 · Jessica Fain
[00:37:50] S0: Right. And I think in that is a disarming of the executive. Again, going back to how do you get the best out of them? You want them to feel comfortable. You want them to feel like they can be honest with you. I think something I see people miss often is they don't follow the subtle threads that executives lead them, the sort of breadcrumbs of opinions. In a more clear cut scenario, your leader, your executive will say to you, "Okay, I'd like a brief on exactly this thing. Write it generally this way. Let's review it in a week." That's a very clear cut ask. But very, very often the asks are more subtle. I wonder if I'm thinking about, have you considered? And what I find is that people don't take the bait. And the best people do. So I'll give you an example. Just last week, we've been working a lot on as skills get democratized across Webflow, everyone can do design, everyone can ship code, everyone can write a PRD. How are we enabling people to move as fast as their brains and tools will make them? Rachel, our CPO said, "Hey, Kev." Our head of design, "We're going to have to think about design reviews at some point." And within an hour, Kev had had a loom put together of, "Hey, here's a framework of high risk design changes, low risk design changes, blast radius, release processes, and how we might allow anyone in the organization to have designs shipped to production." That was a thread. She didn't ask him to do that. He didn't need to follow up in that timeframe, but he recognized that the organization's incentives are to keep empowering people, to keep everyone moving fast, to keep everyone really excited about what they're building as well. And he knew that he could slot in and respond to this feedback really, really quickly. A lot of times I see people don't take that invitation from the executive to actually engage on the subtle feedback they're giving. An example from my past where this didn't go as well was we were in a strategy review, sort of a quarterly strategy review, and it was probably the fourth time I had heard Tamar ask, "I'm interested in seeing the top 10 use cases on X." And the fourth time it happened, she got really frustrated. She said, "We've talked about this so many times before.
00:40:14 · Jessica Fain, Lenny Rachitsky
Why don't we have this documented?" And I think it's because people are not picking up on the cue that there's really something deep underneath. There's really an important piece of feedback or a question that they're not pulling on. Maybe you think that that's not an important thing to do, and then you need more information about why they think it's important. Because if you just let it go and you don't respond to the feedback or respond to the ask, that person loses faith in you, that you're going to follow up on a thing that they believe is important. [00:40:51] S1: And it also sounds like a really good way to influence is you take the reins and here's where I think we could go with this, and here's the answer to your question. [00:41:00] S0: Absolutely. I think if you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset? You have to act like a CPO. You have to come in with that perspective. You have to come in with a solution. You have to follow the thread that they've asked about. You have to do it quickly. One of the missteps here is people treat these interactions as so high stakes. And sometimes they are, but one of the ways that you fail at that interaction is you wait too long to engage on the feedback. If you wait a week for the follow-up items that you discussed in the meeting, that exec has moved on. And you've missed your chance to actually respond to the feedback in a quick manner, you will get so much more excitement, enthusiasm, brain power from them if you keep the ball rolling in a timely manner.
00:41:00 · Jessica Fain, Lenny Rachitsky
[00:41:00] S0: Absolutely. I think if you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset? You have to act like a CPO. You have to come in with that perspective. You have to come in with a solution. You have to follow the thread that they've asked about. You have to do it quickly. One of the missteps here is people treat these interactions as so high stakes. And sometimes they are, but one of the ways that you fail at that interaction is you wait too long to engage on the feedback. If you wait a week for the follow-up items that you discussed in the meeting, that exec has moved on. And you've missed your chance to actually respond to the feedback in a quick manner, you will get so much more excitement, enthusiasm, brain power from them if you keep the ball rolling in a timely manner. [00:41:54] S1: And obviously, everyone's so busy. There's already so much work on their plates. You can't just hop on it. Everything an exec says. There's also this classic advice of sometimes execs just say something and everyone takes it so seriously. "Oh, I have to do that." And sometimes they're just saying it in passing. So it's a balance of take the opportunities, don't [inaudible 00:42:13] single thing.
00:42:13 · Jessica Fain
[00:42:13] S0: Yeah. And a great question to ask in that scenario is how strongly do you feel about this? So if you hear something that they say really strongly, or how urgent do you think that is? Or, "Hey, here's what the team is working on now. Do you think that that trumps these priorities?" And if they say," Yes, listen, do the thing that they say trumps it. "It's not about jumping on every request or taking every piece of feedback, it's about contextualizing it and why they believe that, what they think the urgency is, and then actually responding to that. So more often than not, they'll say," I wonder if we could do this kind of study. "And people will go and say, "Oh my gosh, we have to go run that study right now. We have to deprioritize everything else." But if you say to them, "Hey, that's a really cool idea. I like that. Do you think that that's more important than these three other studies or three other projects that we're working on now?" And they'll say, "Oh no, no, no. That's a random idea. Put it on the backlog." I think that execs are moving so quickly that they won't always give you that context of urgency and so you have to ask for it. This is something I've been working on getting better at as a leader. This is just an idea, this is a mandate, this is something I want to see, but it's hard. Sometimes it's hard to remember to do that because your brain is spinning with ideas.
00:43:33 · Lenny Rachitsky, Jessica Fain
[00:43:33] S1: This comes back to your point about getting into the mind of the person in the meeting, the leader. They're running around all day. I think you call it a strobe. You're just like, bam, another meeting next meeting, next meeting, next meeting without a lot of context and they just say things, and sometimes it's important to them, sometimes not, which comes back to one of your tips at the beginning of this chat is spend 30 to 60 seconds at the beginning just giving them a little context on what the heck. What would you recommend in that 30, 60 seconds? What are some key bullet points of what you want to communicate? [00:44:02] S0: Yeah. In the 30 seconds, I would say, we're here to discuss X, Y, Z. Last time we met, we left it off here. The goals of today's meetings are ZYX. Here's how we're going to run this meeting. And then stop talking Because the moment you go off over 60 seconds, you've lost them. And oh, I think the other really important thing I would add there is to say, was there anything else you were hoping to cover today? [00:44:27] S1: That was awesome. I love this advice. I'm excited to tweet this out just to summarize these bullet points you just shared. That is so cool. I love that. And to your point, if 60 seconds flies by, you may think you're talking for 60 seconds. It often ends up being five minutes. So your advice of keep it under 60 seconds, just try to actually do that.
00:44:46 · Jessica Fain
[00:44:46] S0: Try to actually do that. I think the other thing here is this often depends on what kind of meeting, what you're actually doing. In our culture, we do a lot of silent read of docs or watching a loom in the meeting, and then coming back for conversation. I think one of the things that I've seen be really effective in coming back for that conversation is oftentimes a leader will smatter your doc with 100 comments and you're like, "Oh my gosh, what is actually important here?" So what I often do is I have a section at the top to say themes for discussion. I bubble up some of the biggest and most controversial pieces that can only be discussed live and anything they've said that they're just curious about. What's the timeframe for this? What's the staffing need for why? I can answer offline. I can answer in a follow-up. What I can't get again is the time for discussion with that group. "And the safer that they feel in that discussion and the more that they think that you've understood what is the most spicy or controversial, that's where you get to the good stuff and you really get their insight and input. So I put a section at the top and say topics for discussion that I'm reading through the comments. Rachel, was that right? Did I get your thoughts right? Anything you would add to this? And then we can talk about the really good stuff that gets us to a better outcome.