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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)
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):
Published on 6 months, 2 weeks ago