Navigating Leadership and Self-Discovery

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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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.

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