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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

Some takeaways:

1. Understanding how your CEO and leaders think is 10 times as valuable as knowing what they think. Send your team weekly summaries with verbatim quotes from leadership meetings plus your interpretation of why they said it.

2. Use “magic questions” to decode how people think: Make statements ending with “Do you agree?” instead of asking open-ended questions. This forces you to form hypotheses and calibrate your judgment faster.

3. When someone important thinks negatively about you at work, don’t defend yourself or explain. Instead, take one small action that demonstrates the opposite of what you’re afraid they think. This “counterprogramming” technique stops negative spirals and builds career resilience.

4. Actively teach your team to “take punches,” because the easy problems are solved, and what’s left is hard. People avoid difficult work not due to lack of skill but fear of failure and criticism.

5. Apply behavioral activation from cognitive behavioral therapy to management: Act first, feel better later (not the reverse). If your team is stuck, give them one tiny action to take immediately rather than waiting for motivation.

6. You’re not the protagonist in your company’s story—the CEO is. Your job isn’t to get your ideas implemented but to brilliantly operationalize the CEO’s vision. Find where you can add unique value within that framework.

7. Most PMs are “playing on easy mode” by building products for people like themselves at companies with straightforward business models. The real craft challenges are in regulated industries, vulnerable populations, and complex business models.

8. Ask in every one-on-one: “What did you do for joy today?” If they say nothing, that’s a problem to solve. High performance requires active rest, just like athletes need recovery.

9. Create reward loops that actually change behavior by making them powerful, immediate, and emotional. WHOOP’s red recovery score after drinking changes behavior more effectively than any lecture about alcohol’s effects.

10. Build your team’s confidence to speak in meetings by teaching them they’re “paying a cost” by staying silent—every additional person makes meetings less candid. Help them earn their seat through valuable contributions.

11. When you disagree with leadership decisions, go through the “What if I’m wrong?” exercise. Ask yourself: “In what world does this make sense?” Often you’ll discover insights you were missing.

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

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 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/

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

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.