How to build a team that can “take a punch” | 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:
1. How to teach your team to be able to “take a punch”
2. Specific tactics to counter negative perceptions and reframe setbacks productively
3. Powerful behavioral strategies to form positive habits
4. Practical approaches for creating space in your workday to encourage creativity and deep thinking
5. The underestimated potential of AI in accelerating your personal and professional growth
6. Why you’re not the protagonist at your company (and why that’s liberating)
7. How WHOOP uses reward loops to drive real behavior change

Transcript: https://www.lennysnewsletter.com/p/ho...

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Where to find Hilary Gridley:
• X: https://x.com/yourgirlhils
• LinkedIn:   / hilarygridley  
• Newsletter: https://hils.substack.com/
• Maven course: https://maven.com/hilary-gridley/ai-p...

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X:   / lennysan  
• LinkedIn:   / 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/ho...
• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/ho...
• WHOOP: https://www.whoop.com/
• Big Health: https://www.bighealth.com/
• What is behavioral activation?: https://www.medicalnewstoday.com/arti...
• Will Ahmed on LinkedIn:   / willahmed  
• Joe Gebbia on LinkedIn:   / jgebbia  
• Zach Abrams on LinkedIn:   / 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/th...
• Paths to Power course: https://jeffreypfeffer.com/wp-content...
• 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/...
• The Handle Bar in Boston: https://www.thehandlebarstudios.com/o...
• From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/educat...
• Product Management Logic Coach GPT: https://chatgpt.com/g/g-6732903017008...
• Dropbox: https://www.dropbox.com/
• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/...
• Negative capability: https://en.wikipedia.org/wiki/Negativ...
• John Keats: https://en.wikipedia.org/wiki/John_Keats
...References continued at: https://www.lennysnewsletter.com/p/ho...

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Lenny may be an investor in the companies discussed.