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Hilary Gridley (Head of Core Product, Whoop)15 June 2025

How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams

7Frameworks
15Insights

Frameworks in this episode

Innovation4 steps

AI Rep-Loop Compression

Build AI tools that give you feedback 80% as good as an expert's, on demand, to get years of judgment-building reps in a fraction of the time.

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Self-Mastery3 steps

Behavioral Activation

Act first, then feel better — keep a pre-written list of small actions that reliably reverse a low mood.

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Leadership4 steps

Broadcast How Leaders Think (Mental-Model Transparency)

Teach your team how key leaders think — not just what they decided — via weekly verbatim-plus-interpretation notes.

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Self-Mastery4 steps

Counterprogram the Narrative (Take a Punch)

When you fear someone thinks less of you, take one small action that proves the opposite instead of litigating the past.

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Leadership4 steps

Habit-Formation Model for Team Behavior Change

Drive team adoption (e.g. of AI) with behavioral psychology, not education: consistency, low friction, and a powerful reward loop.

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Communication4 steps

Magic Questions (Statements That End in 'Do You Agree?')

To understand how someone thinks, feed them statements ending in 'is that right?' rather than asking open-ended questions.

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Mindset4 steps

You Are Not the Protagonist (Operationalize, Don't Impose)

Your job isn't to convince everyone of your vision — it's to understand the leader's vision and find the spiky places you can shape it.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take26:00

Too Many PMs Are Playing on Easy Mode

Gridley's self-described hot take: many product people who claim to love craft and taste for its own sake are building for users exactly like themselves at low-stakes B2B companies. She wishes more of that pure love of building were applied to hard spaces — low-income users, social services — that genuinely need it, while acknowledging the prestige and pay pull people elsewhere.

  • Building for people just like you, at companies that don't worry about pricing, is the easy path
  • She wishes more craft-obsessed builders worked on low-income users and social services
  • Prestige and better pay naturally pull talent toward comfortable spaces
  • She shouts out the people already doing hard, important work in hard spaces

“Oh, I think this is my hot take.”

Hillary Gridley · 26:00

“why are you building products for people exactly like you who have all your exact same problems at a company that sells to other companies…”

Hillary Gridley · 26:30
#hot-take#product-management#craft#impact#career
Hot Take50:00

You're Not the Protagonist in the Story of Your Work

A former Coinbase CPO turned Gridley's view of her job upside down: the mistake CPOs make is thinking the game is influencing the CEO to make what's in their own head real. Instead, the job is to understand the CEO's vision and operationalize it. She extends this into a broader life lesson — 'you're not special' — that made her both more effective and genuinely happier.

  • The CPO's job is to understand and operationalize the CEO's vision, not impose their own
  • Everyone operating from their own protagonist viewpoint makes organizations painful and inefficient
  • Accepting 'you're not special' freed her from endlessly trying to convince people
  • This isn't 'just do whatever the boss says' — your unique skills still matter within the shared model

“you kind of come up thinking like you're the protagonist and you can be the protagonist in your life. You can be the protagonist in…”

Hillary Gridley · 51:00

“you're not special.”

Hillary Gridley · 51:30
#hot-take#leadership#ego#product-management#career
Hot Take1:21:30

AI Can Shrink the Learning Loop That Entry-Level Jobs Used to Provide

Gridley challenges the fear that AI eliminating entry-level grunt work will stop the next generation from building judgment. Those jobs built taste through years of reps — but that model is actually inefficient. She builds GPTs that think like her so her team gets ~80% of her feedback on demand, arguing we should still invest in people's skills, just not the slow historical way.

  • Entry-level grunt work builds judgment through many reps over years
  • That grind-wait-for-feedback loop is inefficient when you examine it
  • Her custom GPTs give feedback ~80% as good as hers, instantly and infinitely repeatable
  • We still need to invest in skills — just far faster than the two-year analyst model

“we absolutely still need to be investing in people's skills. I just don't think we need to be investing in them historically in the way…”

Hillary Gridley · 1:23:30

“I build these GPTs that kind of think like me and the purpose of that is so that my team can get feedback that is…”

Hillary Gridley · 1:24:30
#ai#hot-take#learning#career#future-of-work

Explainer· 2

Explainer05:30

Why Teams Need to "Take a Punch" More Than Ever in the AI Era

Gridley argues that AI and constant layoff anxiety have left many workers scared and questioning how they provide value as humans. That fear pushes people toward safe, likely-to-succeed work instead of the hard problems worth doing. She wants managers to be able to lead teams through uncertainty so more people take on important things that might fail.

  • AI adoption is triggering identity fear: people worry what it means for their jobs and self-worth
  • Younger workers have never known a career without the threat of layoffs, taking a psychic toll
  • Fear makes people gravitate to work they're confident they'll succeed at, avoiding hard problems
  • The stuff left to build is hard — hardware, deep tech, ML — so resilience is a core skill now

“And so I think all managers now really need to be able to lead their teams through uncertainty, through fear, through hard things.”

Hillary Gridley · 06:30

“I would really love it if if more people were like, "Screw it. I'm going to do something that's probably going to fail."”

Hillary Gridley · 07:00
#leadership#resilience#ai#career#management
Explainer18:00

Behavioral Activation: Act First, Feel Better Second

Drawing on her work on a clinically validated depression therapeutic at Big Health, Gridley explains the CBT concept of behavioral activation. The instinct in a low mood is to wait until you feel better before acting, but that spiral rarely reverses on its own. The therapeutic move is to identify specific small actions that reliably lift your mood, and act before you feel ready.

  • Depression is characterized by negative thinking and 'I'll act once I feel better' avoidance
  • The misconception is 'I'll feel better and then act'; the fix is 'I act and then I feel better'
  • She keeps a list on her phone of personal behavioral activations for when the walls close in
  • An action can be tiny — even putting a piece of laundry away — and still break the downward spiral

“the sort of like misconception is I'll feel better and then I'll act. And the thing that therapists try to teach people when they're working…”

Hillary Gridley · 19:30
#cbt#mental-health#habits#psychology#management

Story· 5

Story09:30

The Ketamine-Tracking Meeting That Humiliated Her

Gridley laughed when Whoop's CTO suggested tracking ketamine use, assuming it was a joke — and the CTO seriously told her it wasn't funny. Instead of following up to explain herself, she asked what she was afraid the CTO now thought of her and took a small action to prove the opposite: within ten minutes she sent a note proposing sports-betting tracking as another emerging health concern.

  • She was humiliated because the reaction implied she doesn't take health issues or emerging trends seriously
  • Trying to 'correct the record' usually reads as defensive and draws more attention to the mistake
  • She instead researched an emerging public-health issue (sports betting) and proposed tracking it
  • The counterprogramming note took only 5–10 minutes and demonstrated the opposite of her fear

“our chief technology officer suggested ketamine tracking and I thought she was making a joke and I laughed and she looked at me very seriously…”

Hillary Gridley · 10:00

“what is one thing that I can do, small, that will demonstrate the opposite of what I'm afraid this person thinks of me?”

Hillary Gridley · 09:30
#story#ego#self-perception#leadership#whoop
Story32:30

"This Doesn't Feel Like the Future": Decoding Whoop's CEO

Gridley uses Whoop CEO Will's recurring feedback — 'this doesn't feel like the future' — as a worked example of building a mental model of a leader. Teams often misread it as a demand for maximum scope, but she interprets it as finding small, high-impact, low-cost touches (like weaving a user's own data into an AI-coach explanation) that make the product feel magical rather than generic.

  • Will obsesses over pixels and holds a high bar, producing a far better product
  • 'Feel like the future' is commonly misread as 'blow up the scope on everything'
  • The real lever is high-impact, low-cost touches sprinkled through the experience
  • Example: explaining VO2 max by pulling in the user's own data via a conversational AI coach

“we often get feedback from him that's like, you know, this doesn't this doesn't feel like the future and everything that we're building needs to…”

Hillary Gridley · 33:00

“what are those high impact but lowcost ways that we can just find and sprinkle through the experience”

Hillary Gridley · 35:30
#product-design#leadership#whoop#mental-models#ai
Story1:07:30

How Whoop's Red Recovery Score Curbs Drinking

Gridley describes Whoop's recovery score — red, yellow, green each morning — as a powerful anti-reward loop around alcohol. People already knew drinking disrupted their sleep, but seeing the red score the morning after has a profound emotional impact that plain knowledge never had. Members tell her Whoop is what finally helped them get a handle on their drinking.

  • A red recovery score after drinking just 'feels bad' in a way facts alone didn't
  • The information wasn't new — the immediate, emotional feedback loop is what changed behavior
  • Green scores feel great and reinforce healthy self-identity
  • New feature Healthspan tries to extend this reward loop to long-term aging, not just next-day recovery

“if you drink and you're on Whoop, you will very quickly learn that if you anytime you drink, you get a red recovery.”

Hillary Gridley · 1:08:00

“there's something about seeing that like red score that just feels like it just feels bad.”

Hillary Gridley · 1:08:30
#behavior-change#reward-loops#whoop#product-design#habits
Story1:33:30

The Pivotal Moment: Reporting to a CEO by Fire

Gridley's most pivotal career moment was when her boss at Big Health left and she started reporting directly to the CEO — trial by fire. Being in the room finally let her see why leaders reach conclusions that had seemed nonsensical from the rank and file. Her boss Kelvin's advice stuck: product leadership is a role where uncontrolled voices in your head will eat you alive.

  • Working closely with a CEO revealed the pressures and worldview behind decisions that once seemed senseless
  • It reinforced the humility that a leader may be right about something you can't yet see
  • She was terrified but it became an inflection point that grew her confidence
  • It's why she's so regimented about out-of-work recovery — to thrive amid feelings of failure

“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…”

Hillary Gridley · 1:33:30
#story#leadership#career#mental-health#confidence
Story1:37:30

There's Always a Shot Clock (Build vs. Buy)

Gridley's hardest failure was spending about a year on a depression therapeutic that was largely shelved when the company acquired a competing product and merged them. The lesson: on a zero-to-one product you feel you have the luxury of time, but the build-versus-buy question is always live. If development drags and a working solution exists, acquiring it can be the right call — there's always a shot clock, even if you can't see it.

  • A year of heartfelt work on a depression therapeutic never fully saw the light of day
  • Zero-to-one teams overestimate how much time they have to 'get it right'
  • Build-vs-buy is always a live and fair question, whether or not the builder wants to admit it
  • The failure instilled a healthy urgency: ship, because the clock might run out anytime

“there's there's always a shot clock, right? When you're working, especially on a zero to one product”

Hillary Gridley · 1:38:30

“there's there's always a shot clock and you might not be aware of it but it's there.”

Hillary Gridley · 1:39:00
#story#failure#product-strategy#build-vs-buy#urgency

Tool· 2

Tool41:30

"Magic Questions": Statements That End in "Do You Agree?"

Gridley's favorite tool for understanding how someone thinks isn't a question at all — it's a statement that ends with 'do you agree?' or 'is that right?'. By putting concrete facts or proposals in front of legal teams, leaders, or reports and watching what they say yes and no to, she teases out their mental model rather than asking them to explain it. She has her own team do the same to her.

  • Instead of asking open-ended 'why', present a concrete proposal and ask if it's right
  • Especially useful with legal/compliance teams who work from rules but can't articulate them
  • She tells reports to rephrase 'what should I do?' as 'here's what I'd do — do you agree?'
  • It calibrates their judgment over time and stops them being reliant on her for answers

“I talk about what I like to call magic questions, but the thing about magic questions is they're not actually questions. their statements and they…”

Hillary Gridley · 41:30

“I'm sort of teasing out the mental model rather than asking them to explain it to me.”

Hillary Gridley · 43:30
#communication#tool#management#mental-models#coaching
Tool1:26:30

"Aristotle": An LSAT-Style GPT for PM Logic Reps

Gridley built a custom GPT she calls Aristotle that generates LSAT-style logical-reasoning questions set in realistic PM scenarios — conflicting signals from sales, engineering, and metrics — then explains why your multiple-choice answer is right or wrong. It lets product builders get near-infinite reps on logical reasoning and argument-building that would otherwise come up only a few times a week on the job.

  • Prompted to create LSAT-style questions testing logical reasoning in PM scenarios
  • Presents conflicting inputs (sales, engineering, metrics) and asks the logically best path
  • Gives multiple-choice answers and explains why you're right or wrong
  • A related version helps a non-technical PM t-shirt-size engineering scope for practice

“create ELSAT style questions uh to to test logical reasoning but put them in the scenarios of things that a PM would encounter.”

Hillary Gridley · 1:27:30
#tool#ai#product-management#learning#logic

Takeaway· 3

Takeaway29:00

Learn How Your CEO Thinks, Not Just What They Think

Gridley reframes the 'why do 10 people have to sign off on this email' problem as a transparency issue, not a process one. A six-month-old strategy doc goes stale, so what actually scales is teams internalizing how leaders think. She tries to send a weekly Slack rundown of the most important conversations — verbatim quotes, her interpretation, and what she'll do differently — so her team can operate without her approval.

  • Approval bottlenecks are a transparency and communication problem, not a process problem
  • Knowing what a leader thinks goes stale; knowing how they think lets you respond to new situations
  • She shares the 'note behind the note' — why she thinks a leader said something, not just the quote
  • When she trusts a team understands how she thinks, she doesn't need to review their emails

“what is what much more helpful than understanding what your CEO thinks is I think understanding how your CEO thinks.”

Hillary Gridley · 29:30
#management#communication#mental-models#transparency#leadership
Takeaway1:16:30

Ask Your Reports: "Have You Done Anything for Joy Today?"

In one-on-ones, Gridley asks her team whether they're doing something every single day that brings them joy — and treats a 'no' as a problem to solve. Many people don't even know what their joy or recharge activities are, so she helps them experiment and identify them. She frames modeling this as a permission structure so people stop feeling they must be 'so busy' all the time.

  • She asks whether reports are doing something daily that brings them joy
  • A lot of people don't know what their recharge activities even are
  • Being back-to-back in meetings is partly self-inflicted; you have to get yourself out of the weeds
  • Modeling and normalizing hobbies gives the team permission to take back their lives

“I'm asking them like what what do you do for joy? Like are you doing something every single day that's bringing you joy in your…”

Hillary Gridley · 1:16:30
#management#wellbeing#burnout#one-on-ones#leadership
Takeaway1:45:00

Read Fiction to Learn to Sit in Tension

Gridley, a former English major, argues fiction beats business books because it teaches you to sit inside tension and ambiguity — exactly what product work demands. She invokes Keats's 'negative capability': the ability to remain in uncertainties and doubts without irritably reaching after fact and reason. Succeeding as a human in the job, she says, means being able to sit in the mess as well as structure it.

  • She'd skip business books; fiction is what actually shaped how she thinks
  • Fiction teaches you to hold dualities and warring forces within people
  • Keats's 'negative capability' — staying in uncertainty without grasping for answers — fits PM work
  • Product work requires both providing clarity and accepting there's no perfect answer

“what I love about fiction is it just it teaches you how to sit inside tension”

Hillary Gridley · 1:45:30

“John Keats the poet talks about this concept of negative capability which is the ability to remain in uncertainties, mysteries, doubts without any irritable reaching…”

Hillary Gridley · 1:45:30
#takeaway#reading#ambiguity#product-management#philosophy