How Product Leaders
Take a Punch

Hilary Gridley

Head of Core Product, Whoop

RECENT

The Challenge

Leading Through Uncertainty & Fear

AI fear: "What does this mean for my job and identity?"
Generational trauma: Young professionals only know layoff cycles
Risk aversion: Fear drives people toward safe, easier work
The leadership gap: Most managers unprepared to lead through this

"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."

Core Tactic

Counter-Program the Narrative

Don't litigate what already happened
Don't try to convince them otherwise
Ask: "What is one thing I can do that demonstrates the opposite of what I fear they think of me?"

The ketamine story

Laughed at CTO's ketamine tracking idea. Felt humiliated. Instead of defending herself, Hilary researched sports betting (emerging health issue), sent CTO an idea to track it + correlate with stress data. 5 minutes. Flipped the narrative.

≠

litigate

✓

act

Framework

The 3 Rules of Pushback

Know the difference: Vision (CEO's domain) vs. execution (your domain)
Fight the good fight: Advocate hard with data, qual + quant, or whatever you do best
Accept the answer: If you argued well and lost, say "I wasn't seeing something", not "the CEO is wrong"

The hard truthThe CEO owns the vision. Their vision trumps your vision. If you deeply disagree, probably shouldn't work there.

Your real power

You're not influencing the vision. You're figuring out what the vision requires today and tomorrow to become real.

The journey matters

Know where you are: raw opinion? researched position? You don't start from "I have nothing to say." You end there.

Behavior Change

Habits, Not Rules

Use behavioral psychology, not enforcement or measurement
Start small: 1-2 minutes per day, every day
Consistency beats intensity, daily habit > occasional training
Build reward loops, immediate, small wins compound

The 30 days of GPTDaily micro-challenges. One per day. Reduces friction. Gets people using AI as tool. Works because it's habit design, not education design.

Contrarian Takes

What Hilary Actually Believes

✗You're the protagonist of your career storyINSTEAD →✓ In the story of work, you are probably not the protagonist. You're not special.

✗Defend yourself when criticizedINSTEAD →✓ Ruminating on the past makes anxiety spiral. Move forward. Show them who you are through action.

✗Fear means don't try hard thingsINSTEAD →✓ Fear is the signal to take a punch. The hardest, most important problems are worth failing at.

✗Measure adoption with accountabilityINSTEAD →✓ Design habits. Small daily wins create confidence that sticks. Behavioral psychology > enforcement.

Based on Hilary Gridley's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube Follow @yourgirlhils on X

GO DEEPER IN THE EPISODE

04:31 Teaching teams to handle criticism and setbacks 17:57 Behavioral activation and mental health in the workplace 22:59 The importance of putting yourself out there 27:51 Transparency and communication in leadership 38:10 How to respectfully disagree with your manager 41:49 How to use “magic questions” to decode how people think 49:54 Why you’re not the protagonist at your company 52:48 Aligning with the CEO's vision 01:01:02 Building effective habits 01:11:14 Promoting team well-being 01:14:28 Creating space for creativity 01:20:45 AI’s role in accelerating learning 01:30:35 Pivotal career moments 01:37:21 Lessons from failure 01:39:49 Exciting new features of WHOOP 5.0 01:44:19 Lightning round and final thoughts

Every sketch here began as a transcript.

Send us yours and we’ll draw it. $1 a transcript.

Sketch mine →

0:00