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)
Guest Hilary Gridley, Head of Core Product at Whoop, shares high-value insights on building resilient teams and thriving in uncertainty. She discusses tactics for managing negative perceptions, fostering self-care, leveraging AI for accelerated learning, and understanding leadership's mental models to enhance organizational effectiveness.
Deep Dive Analysis
14 Topic Outline
Teaching Teams to Handle Criticism and Setbacks
Behavioral Activation and Mental Health in the Workplace
The Importance of Putting Yourself Out There
Transparency and Downward Communication in Leadership
Respectfully Disagreeing with Your Manager
Using 'Magic Questions' to Understand Others' Thinking
Why You're Not the Protagonist at Your Company
Aligning with the CEO's Vision for Product Development
Building Effective Habits and Reward Loops
Promoting Team Well-being and Work-Life Balance
Creating Space for Creativity and Deep Thinking
AI's Role in Accelerating Learning and Skill Development
Pivotal Career Moments and Lessons from Failure
Exciting New Features of WHOOP 5.0
6 Key Concepts
Taking a Punch
This concept refers to developing the ability to deal with criticism, setbacks, or negative perceptions of your work without getting stuck in rumination. It involves focusing on proactive actions to counter a negative narrative rather than litigating past events or others' impressions.
Behavioral Activation
A concept from cognitive behavioral therapy, it emphasizes that acting can precede feeling better, rather than waiting to feel better before acting. It involves identifying small, specific actions that can reliably lift one's mood or reverse a negative spiral, applicable both in personal life and professional challenges.
Magic Questions
These are not open-ended questions but rather statements ending with 'do you agree?' or 'is that right?'. This technique helps to understand someone's mental model by presenting facts or assertions and observing their agreement or disagreement, allowing for calibration of judgment and deeper insight into their perspective.
Reward Loops
A psychological principle for behavior change, focusing on making desired actions immediately and powerfully rewarding. For habits to form, the reward needs to be immediate, emotional, and powerful, overriding initial discomfort or negative associations with the new behavior.
Healthspan
A WHOOP feature that aims to create a reward loop between daily behaviors and long-term health. It helps users understand how current activities impact their health over decades, providing immediate feedback (e.g., changes in 'WHOOP age' or colors) to motivate healthier habits.
Negative Capability
Coined by poet John Keats, this is the ability to remain in uncertainties, mysteries, and doubts without an irritable reaching after fact and reason. It's about accepting ambiguity and not needing immediate clarity, which is crucial for navigating complex problems in product development and life.
7 Questions Answered
Managers should encourage teams to focus on taking proactive actions to counter perceived negative narratives, rather than dwelling on past events or trying to litigate others' impressions. The goal is to demonstrate desired qualities through future actions, which builds agency and reduces negative rumination.
Instead of asking open-ended questions, use 'magic questions' by making a statement and asking 'do you agree?' or 'is that right?'. This approach helps to tease out their underlying assumptions and reasoning, allowing you to calibrate your own judgment and build a clearer understanding of their viewpoint.
Understanding the CEO's vision and their thought process (how they think, not just what they think) allows employees to operationalize that vision effectively and make decisions that align with the company's strategic direction. This fosters efficiency, reduces miscommunication, and helps identify areas where individual contributions can be most influential.
Habit formation requires consistency, reduced friction, and powerful, immediate, and emotional reward loops. Start with small, easy daily tasks, remove any work pressure by practicing in low-stakes contexts, and ensure that completing the action makes the person feel great.
It involves modeling the behavior of carving out time for personal well-being and creative pursuits, and encouraging team members to identify and prioritize activities that bring them joy. This creates a permission structure within the team to prioritize active rest and heads-down time, which are crucial for creative breakthroughs and preventing burnout.
AI can shrink learning loops by providing on-demand, personalized feedback and practice opportunities that traditionally require human interaction. By building AI tools (like custom GPTs) that mimic expert feedback or create scenario-based training, individuals can get unlimited 'reps' and accelerate their judgment and skill acquisition much faster than traditional methods.
There is always a 'shot clock' on product development, especially for zero-to-one products. While it's important to get things right, there's a point where the build-versus-buy question becomes critical. An urgency to build, ship, and get products out is essential because time can run out, leading to internal projects being superseded by external solutions.
14 Actionable Insights
1. Leverage AI for Learning
Utilize AI tools, like custom GPTs, to create personalized, on-demand learning environments that provide immediate feedback and allow for infinite practice reps. This drastically shrinks learning loops, accelerates skill development, and builds judgment more efficiently than traditional methods.
2. Build Habits with Reward Loops
To build new habits (e.g., AI adoption, self-care), focus on consistency (small, daily actions), reducing friction (start with low-stakes, non-work applications), and designing powerful, immediate, and emotional reward loops. This makes desired behaviors intrinsically motivating.
3. Prioritize Self-Care and Joy
Actively model and encourage self-care and creative pursuits for yourself and your team, recognizing these activities are crucial for well-being, preventing burnout, and improving work performance. Create a ‘permission structure’ by normalizing these discussions and asking about personal joy.
4. Counter Negative Perceptions
When facing criticism or fear of negative perception, identify the narrative you’re afraid of and take a small, immediate action to demonstrate the opposite, rather than defensively litigating the past. This shifts focus to controllable actions and prevents negative spirals.
5. Cultivate Shared Mental Models
Managers should proactively share insights from strategic discussions, explaining not just what was said but why key leaders think that way. This builds shared mental models across the team, improving efficiency and reducing the need for constant approvals.
6. Adopt an Ecosystem Mindset
Shift from a ‘protagonist’ mindset to an ’ecosystem’ view, understanding that your role is to operationalize the CEO’s vision and the company’s shared goals, rather than solely pushing your own agenda. This fosters collaboration and efficiency within the organization.
7. Use Magic Questions
To understand someone’s mental model, use ‘magic questions’ by making statements ending with ‘do you agree?’ or ‘is that right?’. This helps calibrate judgment, reduces reliance on direct answers, and teases out underlying perspectives, provided you approach with genuine curiosity and humility.
8. Navigate Leader Disagreements
When disagreeing with a leader’s decision, first try to understand their perspective by asking ‘what if I’m wrong?’. If you still disagree, candidly explain their rationale to your team, even while stating your own reservations respectfully, and commit to executing the decision to learn from the outcome.
9. Practice Behavioral Activation
To combat negative moods or thinking patterns, proactively identify and take small, specific actions (behavioral activation) that reliably lift your mood, rather than waiting to feel better before acting. This reverses negative spirals and promotes well-being.
10. Embrace Hard, Risky Problems
Encourage yourself and your team to take on challenging problems, even if failure is likely, by fostering an environment where the fear of failure is reduced. This enables growth and tackling important, difficult work.
11. Recognize the Product Shot Clock
Understand that in product development, especially for zero-to-one products, there’s an unstated ‘shot clock’ for delivery. Maintain urgency to build and ship, as delays can lead to build-vs-buy decisions where external solutions might be acquired.
12. Control Inner Voices
As a product leader, cultivate strong self-awareness and control over internal negative self-talk. Understand that potential criticism doesn’t always warrant self-criticism, as this role inherently involves ambiguous decisions that can be picked apart.
13. Cultivate Negative Capability
Develop ’negative capability,’ the ability to comfortably sit with uncertainty, mystery, and doubt without prematurely grasping for definitive answers. This is crucial for navigating ambiguous product challenges and complex human interactions.
14. Value Life’s Difficulties
Embrace and accept the difficult or ‘sucky’ parts of life and work, as these challenges provide contrast and make the positive experiences more meaningful and appreciated.
5 Key Quotes
Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive.
Hilary Gridley
I would really love it if more people were like, screw it, I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well.
Hilary Gridley
You come up thinking like you're the protagonist, but in the story of work, you are probably not the protagonist. You're not special.
Hilary Gridley
If it didn't have the part of the song that sucked, the cool part wouldn't be as cool.
Beavis
Product leadership is a the type of role where if you are not in control of the voices in your head, they will eat you alive.
Calvin Wong (via Hilary Gridley)
3 Protocols
Counter-Programming a Negative Narrative
Hilary Gridley- Acknowledge the feeling of having 'taken a punch' (e.g., misstep, criticism, negative perception).
- Instead of litigating what happened or trying to correct others' impressions, focus on future action.
- Ask yourself: 'What is one small thing I can do next that will demonstrate the opposite of what I'm afraid this person thinks of me?'
- Take that action to proactively shape the narrative and regain a sense of agency.
Understanding Someone's Mental Model (Magic Questions)
Hilary Gridley- Identify the person whose thinking you want to understand.
- Instead of asking open-ended questions, formulate a statement about what you *think* is true or what you *think* they believe.
- End your statement with 'do you agree?' or 'is that right?'
- Observe their reaction and listen to their explanation (if provided) to calibrate your understanding of their perspective.
- Approach with curiosity and humility, expecting to be wrong, to encourage candid responses.
Building Habits (e.g., AI Adoption)
Hilary Gridley- Ensure consistency: Get people doing the desired action every single day.
- Reduce friction: Start with small, easy tasks that take no more than a minute or two, ideally in low-stakes or fun contexts not directly tied to work deadlines.
- Design powerful, immediate, and emotional reward loops: Make sure the person feels great and successful immediately after performing the desired action, overriding any initial discomfort.