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)
June 15, 2025 · 1 h 55 min
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Show notes
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:
() Hilary’s background
() Teaching teams to handle criticism and setbacks
() Behavioral activation and mental health in the workplace
() The importance of putting yourself out there
() Transparency and communication in leadership
() How to respectfully disagree with your manager
() How to use “magic questions” to decode how people think
() Why you’re not the protagonist at your company
() Aligning with the CEO's vision
() Building effective habits
() Promoting team well-being
() Creating space for creativity
() AI’s role in accelerating learning
() Pivotal career moments
() Lessons from failure
() Exciting new features of WHOOP 5.0
() 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):
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