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 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: https://x.com/yourgirlhils • LinkedIn: https://www.linkedin.com/in/hilarygridley/ • Newsletter: https://hils.substack.com/ • Maven course: https://maven.com/hilary-gridley/ai-powered-people-management — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Hilary’s background (04:31) Teaching teams to handle criticism and setbacks (17:57) Behavioral activation and mental health in the workplace (22:59) The importance of putting yourself out there (27:51) Transparency and communication in leadership (38:10) How to respectfully disagree with your manager (41:49) How to use “magic questions” to decode how people think (49:54) Why you’re not the protagonist at your company (52:48) Aligning with the CEO's vision (01:01:02) Building effective habits (01:11:14) Promoting team well-being (01:14:28) Creating space for creativity (01:20:45) AI’s role in accelerating learning (01:30:35) Pivotal career moments (01:37:21) Lessons from failure (01:39:49) Exciting new features of WHOOP 5.0 (01:44:19) Lightning round and final thoughts — Referenced: • How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with • How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager • WHOOP: https://www.whoop.com/ • Big Health: https://www.bighealth.com/ • What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation • Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/ • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/ • Coinbase: https://www.coinbase.com/ • Bridge: https://www.bridge.xyz/ • Stripe: https://stripe.com/ • 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): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer • Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf • VO₂ max: https://en.wikipedia.org/wiki/VO2_max • Peter Attia on X: https://x.com/PeterAttiaMD • Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0 • The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown • From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria • Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach • Dropbox: https://www.dropbox.com/ • WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n • Negative capability: https://en.wikipedia.org/wiki/Negative_capability • John Keats: https://en.wikipedia.org/wiki/John_Keats • The Rehearsal: https://www.hbo.com/the-rehearsal • Zwift: https://www.zwift.com/ • Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg • “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes • Free month of WHOOP: https://join.whoop.com/us/en/hilary/ — Recommended books: • 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/ • Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599 • East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235 • The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/ • Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe