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)
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What does “taking a punch” mean for product leaders and how can it be taught?
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.
You spend a lot of time thinking about how to help your team learn to take a punch.
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 counterprogram 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?
Do you have specific tactics that you teach your team to deal with hardship?
I would really love it if more people were like, screw it, I'm gonna do something that's probably gonna fail. It's important and it's worth doing and I'm gonna do it well.
Is there something you've learned about when your leader tells you to do something you disagree with?
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.
Today, my guest is Hillary Gridley. Hillary is head of core product at Whoop. Previously, she was a 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 our sister podcast, How I AI with Claire Vaux. And not just that. That her episode with Claire is on track to be the most popular episode of the podcast. So, all that to say, Hillary 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 it's good for you, you don't want to miss this episode. A big thank you to Sam Proppus, Danielle Raynel, 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 lenny's newsletter.com and click bundle. With that, I bring you Hillary Gridley. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise features like SAML authentication and skim provisioning.
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Chapters
8 chapters
1
What does “taking a punch” mean for product leaders and how can it be taught?
0:00–5:17
2
How can managers use counter‑programming tactics to re‑frame negative feedback?
5:17–10:42
3
What is behavioral activation and how does it help teams bounce back from setbacks?
10:42–21:42
4
Why is building a shared mental model of the CEO’s thinking crucial for transparency?
21:42–1:01:15
5
How does Hilary explain habit formation and reward loops for teams?
1:01:15–1:11:48
6
What practical steps does Hilary share for carving out creative space in a busy workday?
1:11:48–1:20:17
7
Why does Hilary think AI is still undervalued for personal and professional growth?
1:20:17–1:41:25
8
What are Hilary’s pivotal career moments and how do they shape her leadership philosophy?
1:41:25–1:54:35
Speakers
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