Lenny's Podcast: Product | Career | Growth

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

AI Summary

5 min read

Hilary Gridley, head of core product at Whoop, shares tactics for leading teams through uncertainty, setbacks, and hard problems like those in regulated health tech and AI shifts. Drawing from cognitive behavioral therapy (CBT) and her experience at Whoop, Big Health, and Dropbox, she emphasizes building resilience by focusing on actionable behaviors over rumination.

Recovering from criticism by counter-programming

When team members feel humiliated by feedback or missteps—like Gridley's laugh at a ketamine tracking suggestion, mistaken for dismissal—she redirects them from defending the past to a small, immediate action proving the opposite of the feared impression. Ask: "What one thing can you do to demonstrate you're not who you think they see?" This behavioral activation from CBT breaks negative spirals, restores agency, and works best for self-critical people by prioritizing control over others' unchangeable views. It prevents defensive litigation, which amplifies scrutiny, and encourages risk-taking on tough projects.

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What you'll learn

1 `* (00:05:00) **Intro to "Taking a Punch": Building Resilience in Uncertain Times**`
2 `* (00:08:05) **Counter-Program the Narrative: Key Tactic for Criticism**`
3 `* (00:18:08) **Behavioral Activation from CBT: Act to Shift Mood**`
4 `* (00:23:13) **Overcoming Fear to Speak Up and Tackle Hard Problems**`
5 `* (00:28:13) **Transparency: Share Mental Models of Leaders**`
6 `* (00:38:10) **Handling Leader Disagreements + Magic Questions**`
7 `* (01:01:49) **Habit Formation: Consistency, Friction, Rewards**`

+ Full timestamped outline available in the app

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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