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)

**Hilary Gridley** (0:00)
Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive.

**Lenny Rachitsky** (0:07)
You spend a lot of time thinking about how to help your team learn to take a punch.

**Hilary Gridley** (0:10)
If they come to me and they're upset, I try to focus them less around how you litigate another person's impression of you and more on what is the action that you can take to counter program the narrative that you are afraid that this other person has of you. What are you going to do next to demonstrate that you are the person that you know yourself to be?

**Lenny Rachitsky** (0:28)
Do you have specific tactics that you teach your team to deal with hardship?

**Hilary Gridley** (0:31)
I would really love it if more people were like, screw it, I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well.

**Lenny Rachitsky** (0:37)
Is there something you've learned about when your leader tells you to do something you disagree with?

**Hilary Gridley** (0:41)
People think that the game is all about influencing the CEO, influencing the people around them. You come up thinking like you're the protagonist, but in the story of work, you are probably not the protagonist. You're not special.

**Lenny Rachitsky** (0:53)
Today my guest is Hilary Gridley. Hilary is head of core product at WHOOP. Previously, she was Senior Director of Product at Big Health and a Senior Product Marketing Manager at Dropbox. Even more importantly, she wrote what is now the sixth most popular post of all time in my newsletter, How to Become a Super Manager with AI. She's also the first ever crossover guest between this podcast and her sister podcast, How I AI with Claire Vaux. And not just that, her episode with Claire is on track to be the most popular episode of the podcast. So all that to say, Hilary is incredible and I'm so excited to continue learning from her. This conversation is packed with advice that will make you a better product leader, builder, and also just a better human. If you know what's good for you, you don't want to miss this episode. A big thank you to Sam Propis, Danielle Reynold and Kelvin Wong for sharing suggestions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Superhuman, Notion, Linear, Perplexity, and Granola. Check it out at lennysnewsletter.com and click bundle. With that, I bring you Hilary Gridley. This episode is brought to you by Work OS. If you're building a SaaS app, at some point your customers will start asking for enterprise features, like SAML authentication and skim provisioning. That's where Work OS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by Work OS, including ones you probably know, like Vercell, Webflow and Loom. Work OS also recently acquired Warrant, the fine-grain authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, skim or user management, you should consider Work OS. It's a drop-in replacement for Auth0 and supports up to 1 million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. This episode is brought to you by Persona, the adaptable identity platform that helps businesses fight fraud, meet compliance requirements, and build trust. While you're listening to this right now, how do you know that you're really listening to me, Lenny? These days, it's easier than ever for fraudsters to steal PII.
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Hilary, thank you so much for being here and welcome to the podcast.

**Hilary Gridley** (4:39)
Thank you, Lenny, I'm so excited to be here.

**Lenny Rachitsky** (4:41)
I talked to a bunch of people that have worked with you about what we should talk about and what you're amazing at. First of all, every one of them loves working with you so much. One of them is like, I joined WHOOP just to work with Hilary, I'm really proud of her. And of that, there's kind of this theme that emerged that I think is a good kind of overarching theme for our conversation. And it's something that you spent a lot of time thinking about. And it's how to help your team and how to help people within your company learn to take a punch.