Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox. In this episode, you’ll learn: • How to teach your team to be able to “take a punch” • Specific tactics to counter negative perceptions and reframe setbacks productively • Powerful behavioral strategies to form positive habits • Practical approaches for creating space in your workday to encourage creativity and deep thinking • The underestimated potential of AI in accelerating your personal and professional growth • Why you’re not the protagonist at your company (and why that’s liberating) • How WHOOP uses reward loops to drive real behavior change — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Persona—A global leader in digital identity verification Attio—The powerful, flexible CRM for fast-growing startups — Where to find Hilary Gridley: • X: x.com/yourgirlhils • LinkedIn: linkedin.com/in/hilarygridley • Newsletter: hils.substack.com • Maven course: maven.com/hilary-gridley/ai-pow… — Where to find Lenny: • Newsletter: lennysnewsletter.com • X: twitter.com/lennysan • LinkedIn: — In this episode, we cover: — Referenced: • How to become a supermanager with AI: • How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): • WHOOP: • Big Health: • What is behavioral activation?: • Will Ahmed on LinkedIn: • Joe Gebbia on LinkedIn: • Zach Abrams on LinkedIn: • Coinbase: • Bridge: • Stripe: • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): • Paths to Power course: • VO₂ max: • Peter Attia on X: • Hilary Gridley’s 30 days of GPT: • The Handle Bar in Boston: • From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: • Product Management Logic Coach GPT: • Dropbox: • WHOOP Advanced Labs: • Negative capability: • John Keats: • The Rehearsal: • Zwift: • Beavis and Butthead Do ‘Creep’: • “Sea Grapes” by Derek Walcott: • Free month of WHOOP: — Recommended books: • 7 Rules of Power: • Outlive: The Science and Art of Longevity: • East of Eden: • The Sun Also Rises: • Anna Karenina: — Production and marketing by . For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed.