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
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Persona—A global leader in digital identity verification
Attio—The powerful, flexible CRM for fast-growing startups
—
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
—
Where to find Lenny:
- Newsletter: https://www.lennysnewsletter.com
- X: https://twitter.com/lennysan
- LinkedIn: https://www.linkedin.com/in/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/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 Bost
