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)

Overview

This episode dives into Hilary Gridley's playbook for building resilient, high-performing teams. As Head of Core Product at WHOOP, Hilary shares actionable strategies for teaching teams to handle setbacks, fostering creativity, leveraging AI for personal and professional growth, and creating impactful reward systems. The conversation also explores the importance of understanding organizational dynamics and embracing humility in leadership.

Notable Quotes

- If you are not in control of the voices in your head, they will eat you alive. — Hilary Gridley, on the mental challenges of product leadership.

- What are you going to do next to demonstrate that you are the person that you know yourself to be? — Hilary Gridley, on reframing setbacks into action.

- If it didn’t have the parts that sucked, the cool parts wouldn’t be as cool. — Hilary Gridley, quoting Beavis and Butt-Head, on embracing life’s dualities.

🛡️ Building Resilience in Teams

- Hilary emphasizes teaching teams how to take a punch by focusing on actionable steps rather than dwelling on others' perceptions.

- She advises counter-programming negative narratives by demonstrating the opposite of what you fear others think of you.

- Managers should challenge negative thinking patterns and help their teams focus on what they can control.

- Drawing from cognitive behavioral therapy, Hilary highlights the importance of behavioral activation—taking small actions to reverse negative spirals.

🧠 Leveraging AI for Growth

- Hilary advocates for using AI to accelerate learning and skill-building, shrinking feedback loops and increasing reps.

- She developed tools like Aristotle GPT, which creates product management scenarios to test logical reasoning and decision-making.

- AI can provide on-demand feedback, enabling faster skill development without waiting for human input.

- She challenges the traditional inefficiencies of entry-level roles, suggesting AI can make learning more engaging and effective.

🎨 Creating Space for Creativity and Joy

- Hilary models the importance of carving out time for creativity and personal joy, asking her team in one-on-ones, Are you doing something every day that brings you joy?

- She normalizes hobbies and self-care, rewarding team members for prioritizing their well-being.

- To foster creativity, she emphasizes the need for active rest and heads-down time, likening it to recovery in athletics.

🎯 Reward Loops and Behavior Change

- WHOOP’s product design leverages powerful reward loops to drive behavior change, such as showing how alcohol consumption impacts recovery scores.

- The new Healthspan feature connects daily habits to long-term health outcomes, offering actionable coaching and immediate feedback.

- Hilary applies similar principles to her team, celebrating small wins and creating emotional, immediate rewards for desired behaviors.

🏛️ Navigating Organizational Dynamics

- Hilary stresses the importance of understanding how leaders think rather than just what they think.

- She encourages building mental models of key stakeholders to anticipate their responses and align with their vision.

- Leaders should balance advocating for their ideas with humility, recognizing when others’ perspectives might hold valuable insights.

- She reframes the role of product leaders as operationalizing the CEO’s vision rather than being the protagonist of the company’s story.