Hilary Gridley on Taking a Punch, Transparency, and Helping Teams Do Hard Things

Hilary Gridley on Taking a Punch, Transparency, and Helping Teams Do Hard Things

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Hilary Gridley on Taking a Punch, Transparency, and Helping Teams Do Hard Things

Source: Lenny’s Podcast Speaker: Hilary Gridley Link: Episode

Overview

Hilary Gridley is head of core product at Whoop; previously senior director of product at Big Health and senior PMM at Dropbox. She wrote the sixth most-read post in Lenny’s Newsletter, “How to Become a Super Manager with AI,” and teaches a Maven course on the same topic. The episode covers her framework for helping teams handle setbacks and do hard things — drawn from CBT’s behavioural activation — alongside transparency as a management practice, habit formation for AI adoption, “magic questions” for understanding how anyone thinks, and the liberating idea that in a company’s story, you are probably not the protagonist.

Key ideas

  • Take a punch — counter-program, don’t litigate. When you feel ego-injured at work (a poorly received comment, critical feedback, a misread moment), resist the urge to correct the record. Instead, ask: what is one small thing I can do to demonstrate the opposite of what I am afraid this person thinks of me? Drawn from CBT’s behavioural activation: act first, feel better second. Gives people agency rather than spiralling over impressions they cannot control. Second-order effect: people who know how to take a punch are less afraid of speaking up in meetings — they stop avoiding exposure because they know how to recover.
  • Transparency as teaching how leaders think, not what they decided. The reason teams need 10 sign-offs on an email is not a process problem — it is a transparency problem. People are working from different mental models of how strategic leaders think. Solution: share the note behind the note — in a weekly Slack message or team meeting, relay verbatim what important people said, then give your interpretation of why they said it and how you’re adjusting. Over time the team builds a shared mental model and can operate without approval chains.
  • Not the protagonist. Reporting directly to a CEO teaches product leaders that their job is to understand and operationalise the CEO’s vision — not to push their own. “In the story of work, you are probably not the protagonist.” The counterintuitive liberation: once you stop fighting immovable forces, you can find the genuine gaps where your specific insight and taste are actually influential. Fulfilment comes from being the person whose presence made the product different, not from winning every argument.
  • Habit formation: consistency, friction, reward loop. Three levers for changing team behaviour: (1) consistency — daily, tiny, starting super easy; (2) friction reduction — start with fun use cases that carry no work-deadline pressure, not live project tasks; (3) powerful, immediate, emotional reward loop — when someone does the target behaviour, they must feel like a million bucks. Applied to AI adoption: 30 days of GPT starts with planning a holiday, not writing a spec. Applied to team culture: publicly reward self-care and creative activities, not weekend heroics. WHOOP’s red/green recovery score is a masterclass in anti-reward and reward loop design.
  • Magic questions. To understand how someone thinks, do not ask open-ended questions — make statements and ask “do you agree?” or “is that right?” Surfaces the mental model through yes/no calibration rather than expecting articulation. Applied to regulatory/legal reviews: “what if we did X — would that be okay?” Applied to coaching reports: “tell me what you think you could have done differently. Do you agree?” Builds their judgment instead of creating reliance on yours.