How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Hilary Gridley (guest), Lenny Rachitsky (host), Narrator, Narrator, Narrator
In this episode of Lenny's Podcast, featuring Hilary Gridley and Lenny Rachitsky, How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop) explores build resilient product teams: taking punches, learning fast, embracing AI Hilary Gridley, Head of Core Product at Whoop, shares how she builds product teams that can “take a punch” and thrive amid criticism, uncertainty, and hard problems. She reframes setbacks as triggers for small, intentional actions—drawing on cognitive behavioral therapy concepts like behavioral activation—to stop negative spirals and reassert agency.
Build resilient product teams: taking punches, learning fast, embracing AI
Hilary Gridley, Head of Core Product at Whoop, shares how she builds product teams that can “take a punch” and thrive amid criticism, uncertainty, and hard problems. She reframes setbacks as triggers for small, intentional actions—drawing on cognitive behavioral therapy concepts like behavioral activation—to stop negative spirals and reassert agency.
Hilary explains how she makes her team dramatically more effective by transparently modeling how senior leaders think, teaching “magic questions” to decode others’ mental models, and balancing personal conviction with humility when disagreeing with executives. She also discusses designing powerful reward loops—both in products like Whoop and in team culture—to build habits around AI, learning, and self-care.
Throughout, she challenges PMs to stop “playing on easy mode,” take on harder, more meaningful problems, and create lives that include joy, creativity, and recovery instead of nonstop grind.
The conversation closes with an overview of Whoop’s new health and healthspan features, and how the product itself embodies many of the behavior-change and feedback-loop principles Hilary uses with her teams.
Key Takeaways
Convert ego hits into small, corrective actions instead of rumination.
When you feel criticized or misjudged, don’t argue the past or obsess over what others think. ...
Get the full analysis with uListen AI
Use behavioral activation: act first to feel better, not vice versa.
Borrowed from CBT, behavioral activation says you don’t wait to feel motivated before acting; you take small, mood-lifting actions to break negative spirals. ...
Get the full analysis with uListen AI
Teach your team how leaders think, not just what leaders decided.
Hilary regularly debriefs her team on key meetings: what senior leaders said, how she interprets it, and what she’ll do differently. ...
Get the full analysis with uListen AI
Use “magic questions” to reverse-engineer others’ mental models.
Instead of open-ended “What should I do? ...
Get the full analysis with uListen AI
Separate conviction from protagonism when you disagree with leadership.
Your job isn’t to impose your internal vision on the CEO; it’s to deeply understand their vision and operationalize it as brilliantly as possible. ...
Get the full analysis with uListen AI
Design powerful, emotional reward loops for both users and teams.
In Whoop, red/green recovery and healthspan visuals turn invisible behaviors (like drinking or sleep) into immediate, emotionally salient feedback. ...
Get the full analysis with uListen AI
Use AI as a force multiplier for learning, not just productivity.
Custom GPTs (e. ...
Get the full analysis with uListen AI
Notable Quotes
“If you are not in control of the voices in your head, they will eat you alive.”
— Hilary Gridley (via advice from Kelvin Wong)
“What is one thing that I can do, small, that will demonstrate the opposite of what I'm afraid this person thinks of me?”
— Hilary Gridley
“In the story of work, you are probably not the protagonist. You're not special.”
— Hilary Gridley
“People are really good at coming up with very rational-sounding reasons to not do things that just make them uncomfortable.”
— Hilary Gridley
“If they didn't have the part of the song that sucked, the cool part wouldn't be as cool.”
— Hilary Gridley (quoting Beavis and Butt-Head)
Questions Answered in This Episode
How would my career change if I consistently applied Hilary’s “counter-program the narrative” tactic every time I felt criticized or misunderstood?
Hilary Gridley, Head of Core Product at Whoop, shares how she builds product teams that can “take a punch” and thrive amid criticism, uncertainty, and hard problems. ...
Get the full analysis with uListen AI
What concrete steps can I take in the next month to better understand how my CEO or VP actually thinks, rather than just what they decide?
Hilary explains how she makes her team dramatically more effective by transparently modeling how senior leaders think, teaching “magic questions” to decode others’ mental models, and balancing personal conviction with humility when disagreeing with executives. ...
Get the full analysis with uListen AI
Where am I currently playing on “easy mode” in my product work, and what harder, more meaningful problems could I choose to tackle instead?
Throughout, she challenges PMs to stop “playing on easy mode,” take on harder, more meaningful problems, and create lives that include joy, creativity, and recovery instead of nonstop grind.
Get the full analysis with uListen AI
How could I redesign my team’s workflows and rituals to include explicit reward loops for the behaviors we say we value (e.g., AI usage, deep thinking, self-care)?
The conversation closes with an overview of Whoop’s new health and healthspan features, and how the product itself embodies many of the behavior-change and feedback-loop principles Hilary uses with her teams.
Get the full analysis with uListen AI
If I built a custom GPT that modeled my own or my manager’s feedback, what skills could I realistically accelerate in myself or my team over the next year?
Get the full analysis with uListen AI
Transcript Preview
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 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?
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 Supermanager with AI. She's also the first ever crossover guest between this podcast and our sister podcast, How I AI with Claire Veaux. 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 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 what's good for you, you don't wanna miss this episode. A big thank you to Sam Proppas, Danielle Reynal, 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 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 SCIM provisioning. That's where WorkOS 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 WorkOS, including ones you probably know like Vercel, Webflow, and Loom. WorkOS also recently acquired Warrant, the fine-grained 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, SCIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to one 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, faces, and identities. That's where Persona comes in. Persona helps leading companies like LinkedIn, Etsy, and Twilio securely verify individuals and businesses across the world. What sets Persona apart is its configurability. Every company has different needs depending on its industry, use cases, risk tolerance, and user demographics. That's why Persona offers flexible building blocks that allow you to build tailored collection and verification flows that maximize conversion while minimizing risk. Plus, Persona's orchestration tools automate your identity process so that you can fight rapidly shifting fraud and meet new waves of regulation. Whether you're a startup or an enterprise business, Persona has a plan for you. Learn more at withpersona.com/lenny. Again, that's withpersona.com/lenny. Hillary, thank you so much for being here and welcome to the podcast.
Install uListen to search the full transcript and get AI-powered insights
Get Full TranscriptGet more from every podcast
AI summaries, searchable transcripts, and fact-checking. Free forever.
Add to Chrome