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) · Lenny's Podcast: Product | Career | Growth summary

Key takeaways

Teach your team to handle criticism by focusing on actionable steps to regain control.
AI has enormous potential to enhance productivity and learning in product management.
Creating space for creativity and deep work is crucial for personal and team success.
Understanding how leaders think can improve communication and alignment within organizations.
Modeling healthy habits and well-being promotes a positive work environment.

Summary

Building Resilience and Handling Setbacks

In the episode, Hilary emphasizes the importance of teaching teams to handle criticism and setbacks. She provides tactics for countering negative perceptions, focusing on actionable steps to regain control in challenging situations. Hilary shares how to reframe setbacks productively, advocating for a mindset that encourages taking on difficult tasks.

The Role of AI in Product Management

Hilary discusses the exciting potential of AI in product management, emphasizing how AI can enhance productivity and decision-making. She talks about the importance of leveraging AI tools for personal and team development, suggesting that AI can help individuals accelerate their learning and improve their decision-making abilities.

Creating Space for Creativity and Deep Work

The conversation touches on the need for leaders to prioritize creativity and deep thinking in their teams. Hilary stresses the importance of carving out time amidst busy schedules to allow for reflection and innovative thinking. She shares personal strategies for achieving balance and encourages team members to pursue joy outside of work.

Navigating Organizational Dynamics

Hilary shares insights on effectively navigating the complexities of organizational dynamics. She highlights the importance of transparency and communication, advocating for managers to help their teams understand how leaders think. This understanding can lead to better alignment and effectiveness in executing strategies.

Promoting Well-Being and Healthy Habits

Hilary discusses how to foster a culture of well-being within teams. She emphasizes the importance of modeling healthy habits and self-care, sharing her personal experiences and how encouraging team members to prioritize their health can lead to better performance at work.

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:

(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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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)