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Hilary Gridley: belief

15 Jun 2025 Lenny's Podcast How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

“The times where I feel like I need to do that is because I'm working with people where I'm like, I don't have confidence that these people understand how I think, or I don't have confidence that they understand how this email or whatever it is, is going to be received by this important person.”

— Hilary Gridley

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Everything needed to verify it.

Speaker
Hilary Gridley
Attribution
Verified speaker
Claim type
belief
Recorded
15 Jun 2025
Publisher
Lenny's Podcast

Transcript context

…Awesome. Okay, I'm glad you shared that. Thank you. I think this will resonate with a lot of people. I want to move on to another trait/habits/skill that you are good at and help people learn, which is being very transparent in what's happening within the organization, within your thinking. You almost help people think the way you think and see the way you think so that they can operate at a higher level. Just talk about that, what that looks like and why that's important. It's interesting, I think another thing I hear a lot of people complain about in organizations is the why do 10 people have to sign off on this email before I send it kind of problem. And I think the answer to that is because those 10 people all have different information, different context, and in many cases, completely different working models for how the CEO of the company and other strategic leaders in the company think. And it makes things super inefficient. I think people will often say like, "Oh, it's a process problem." It's not a process problem. It's not approval problem. I think it's a transparency and it's communication problem, like downward communication, outward communication. And what I mean by that is when I think about artifact-based communication, so reading a strategy document for... About artifact-based communication. So reading a strategy document, for example. Everyone at the company reads the strategy document. Great. Everyone is working from the same idea of what the strategy is. But then things change, right? Especially if you're working in a really dynamic space, new competitive threats emerge, new opportunities emerge all the time. This is especially true now with AI. Obviously everyone is lighting their strategies on fire and trying to figure out the best way to sort of transform their organization. And so if the way that you understand what's going on at the company is from reading a document that was written six months ago, you're going to be working from outdated information and you're not going to be able to think and respond to new things that happen. And so what is much more helpful than understanding what your CEO thinks is, I think understanding how your CEO thinks. And that goes for all sorts of levels of the company. I want to understand how all the strategic leaders at my company think, and I want my team to understand how I think. And when I feel confident that people on my team understand how I think, I don't need to read their emails, I don't need to approve things. The times where I feel like I need to do that is because I'm working with people where I'm like, I don't have confidence that these people understand how I think, or I don't have confidence that they understand how this email or whatever it is, is going to be received by this important person. And so I try to teach that to my team. And the way that I do that is a few ways. First, I'm in meetings with people, important people at the company. So I'm constantly hearing the things that they're saying and paying attention to sort of the note behind the note. Why do I think they're saying this? What insight do they have that they're bringing to this conversation that might not be obvious? And I try to make an effort every week. I don't always do it, but I try to send my team just a quick rundown in Slack of, "Here are the most important conversations or the most interesting conversations I had this week. Here's what that person said verbatim." t, but I try to send my team just a quick rundown in Slack of, "Here are the most important conversations or the most interesting conversations I had this week. Here's what that person said verbatim." Again, I write a lot of notes so I've got it. If you've got a transcriber, maybe that'll help you. "And here's what I interpret that as. Here's why I think they say that. Here's where I think that's coming from and here's what I'm going to do differently as a result." And these aren't long. And sometimes if I don't have time, I'll just, in a team meeting, I'll literally just go through my notes from the week and sort of voiceover stuff and editorialize it as I go. And over time, I think my team has a pretty good sense of what people are saying and how to think about the thinking behind it and how this person thinks, how this person thinks and how I think. And I think when you get an entire organization working that way where everyone's working from the same models of what the CEO thinks matters, what level of risk tolerance the company has, things like that, then you can actually start to move much, much faster and communication becomes much, much, much less painful.…

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