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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)

Posted on June 15, 2025

TL;DR Summary of Building Resilient Product Teams with Hilary Gridley

Hilary Gridley shares actionable strategies to help product teams develop resilience and effectively handle criticism and setbacks. She emphasizes using behavioral activation techniques to motivate teams and foster positive habits. Understanding leadership mindsets and aligning with the CEO’s vision are key to operational success. Additionally, Hilary highlights the transformative role of AI in accelerating personal and professional growth within high-stakes industries.

Optimixed’s Overview: How to Foster Resilience and Drive Growth in Product Teams

Creating Teams That Can “Take a Punch”

Hilary Gridley, Head of Core Product at WHOOP, offers deep insights into building product teams capable of navigating complex challenges, especially in regulated and high-pressure environments. Her approach centers on teaching teams to embrace setbacks as learning opportunities and to develop mental toughness.

Key Behavioral Strategies for Team Success

  • Counterprogramming Negative Perceptions: Instead of defending against criticism, take small actions that contradict negative judgments to build resilience.
  • Behavioral Activation: Encourage immediate action to break inertia, helping teams move forward even without full motivation.
  • Magic Questions: Use statements ending with “Do you agree?” to decode thinking patterns and accelerate judgment calibration.

Aligning with Leadership and Driving Impact

Hilary stresses the importance of understanding how CEOs and leadership think rather than just what they think. Product managers should focus on operationalizing the CEO’s vision and finding unique ways to add value within that framework to advance their careers.

Promoting Well-being and Creativity

  • Regularly check in on team members’ joy and encourage active rest to sustain high performance.
  • Create reward loops that make behavior change immediate, emotional, and impactful, as exemplified by WHOOP’s health metrics.
  • Encourage open communication and help team members build confidence to contribute meaningfully in meetings.

The Role of AI in Accelerating Growth

Hilary highlights AI’s underestimated potential to enhance learning and management practices, helping product leaders become more effective and adaptive in fast-evolving industries.

Source: Lenny’s Newsletter by Lenny Rachitsky. Read original article.

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