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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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Jun 15, 2025

Guest

Hilary Gridley

Hilary Gridley, Head of Core Product at WHOOP, discusses building resilient teams in high-stakes environments. She shares actionable tactics for overcoming negative perceptions and fostering a supportive culture. Hilary reveals the underestimated role of AI in growth and how habits shape productivity. She emphasizes the importance of transparency in leadership and the need for empathy within teams. Listeners can expect insights on creating space for creativity and the significance of mental models in navigating organizational challenges.

01:54:39

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Episode notes

Understand and Respect Leader's View

Strive to deeply understand your leader's viewpoint by framing statements and seeking agreement.
Respectful, evidence-based advocacy matters, followed by humility if your position isn't adopted.

You Are Not the Protagonist

Your job is to understand the CEO's vision and operationalize it, not to just influence or impose your own vision.
Recognize that you are not the protagonist in your company’s story.

Habit Building with Reward Loops

Build habits by ensuring actions are consistent, easy, and provide immediate, emotional rewards.
Start small, reduce friction, and design strong reward loops to encourage daily AI tool use and learning.

Get the Snipd Podcast app to discover more snips from this episode

Cultivating Resilience in Teams

04:41 • 21min

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Empowering Product Management Through Transparency

25:58 • 23min

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Navigating Leadership Alignment

48:55 • 11min

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Building Productive Habits

01:00:02 • 11min

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Cultivating Team Culture and AI Integration

01:10:59 • 20min

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Navigating Leadership and Self-Discovery

01:30:30 • 10min

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Whoop's Health Revolution

01:40:02 • 7min

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Exploring Literature, Emotions, and Innovative Fitness

01:46:37 • 3min

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Balancing Obsession and Responsibility: Lessons from Fiction and Humor

01:49:22 • 3min

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Engaging with AI and Community: Final Insights and Offers

01:52:30 • 2min

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#117

• Mentioned in 159 episodes

Anna Karenina

Leo Tolstoy

Published in 1878, 'Anna Karenina' is a novel by Leo Tolstoy that delves into the complexities of Russian society in the late 19th century. The story centers around the extramarital affair between Anna Karenina, a married socialite, and Count Alexei Kirillovich Vronsky, which scandalizes the social circles of Saint Petersburg. The novel also follows the parallel story of Konstantin Levin, a wealthy landowner, and his struggles with marriage, faith, and managing his estate. Tolstoy explores a wide range of themes including love, loyalty, betrayal, hypocrisy, and the differences between rural and urban life. The novel is known for its detailed character development and its profound commentary on the human condition.

#537

• Mentioned in 57 episodes

East of Eden

Paul Osborn

In 'East of Eden', John Steinbeck tells the story of the Trask and Hamilton families, set against the backdrop of California's Salinas Valley. The novel is a modern retelling of the biblical story of Cain and Abel, focusing on the tumultuous relationship between Cal and Aron Trask, and their struggles with their father, Adam. The book delves into themes of love, rejection, and the choice between good and evil, symbolized by the Hebrew word 'timshel', meaning 'thou mayest'. The narrative is rich with characters like Samuel Hamilton, a kind and wise patriarch, and Kate, the embodiment of evil, whose past and actions significantly impact the lives of the Trasks.

#594

• Mentioned in 54 episodes

The sun also rises

Ernest Hemingway

Originally published in 1926, 'The Sun Also Rises' is Ernest Hemingway’s first novel and a classic example of his spare but powerful writing style. The novel follows a group of young American and British expatriates as they wander through Europe in the mid-1920s, capturing the moods, feelings, and attitudes of the cynical and disillusioned Lost Generation. The story centers around Jake Barnes, a World War I veteran and journalist, and Lady Brett Ashley, as they journey from the wild nightlife of 1920s Paris to the brutal bullfighting rings of Spain. The novel portrays an age of moral bankruptcy, spiritual dissolution, unrealized love, and vanishing illusions, reflecting the existential disillusionment characteristic of the Lost Generation.

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

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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

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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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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/

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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

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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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

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