Hilary Gridley
Product leader; head of core product at WHOOP in 2025, earlier a senior director of product at Big Health; writes the newsletter writerbuilder.
Hilary Gridley did not write this page.
We collected these quotes from things they published elsewhere, and every quote links to where it was said. They have no account here and have not endorsed this site. Quotes are word for word; the short line under each one is our own restatement, not their wording. Their own site. Is this you? Claim it or ask us to remove it. Or tell us what is wrong here.
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Their wordsThis is why I tell my team that if they ONLY check in with me ONCE during the course of the project, it should be here, after the project plan. If we get fully aligned on the problem and the plan, we will save ourselves a lot of heartache down the road.
- 6 weeks earlier
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Their wordsAnyway. The management trainings are right about one thing: you do not want your team to rely on you to solve every problem, or to repeatedly defer to your judgment instead of developing their own. But open-ended questions are not the only alternative to handing someone the answer.
↗against socratic managementhils.substack.com 1st of 2 in this piece
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Our reading
Feedback aimed at fixing one specific piece of work creates a bottleneck rather than leverage.
Their wordsWhen you orient your feedback around fixing one specific piece of work or solving one specific problem, it is not easily generalizable. It provides no insight into how to solve a similar but different problem. If the job of a manager is to create leverage, this does the opposite: it creates a bottleneck.
↗against socratic managementhils.substack.com 2nd of 2 in this piece
- 2 weeks earlier
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Their wordsBut if it becomes your default, you cap the technology at what a more junior version of you might do. You find yourself delegating tasks a person could theoretically take off your plate, instead of imagining a different way of working.
↗insanely specific creative toolshils.substack.com 1st of 3 in this piece
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Their wordsThis is a very different model: unlike an intern, who takes work off your plate, a blacksmith expands what your hands can do.
↗insanely specific creative toolshils.substack.com 2nd of 3 in this piece
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Their wordsNow, it’s cheap for anyone to make a tool for themselves that fits their extremely specific needs.
↗insanely specific creative toolshils.substack.com 3rd of 3 in this piece
- 13 days earlier
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Our reading
People are bad at predicting their own preferences; the option they actually pick is more telling.
Their wordsYou are essentially doing user research on yourself. Asking yourself “what would I like?” will result in unreliable answers for the same reason that asking users what they would like does -- people are bad at predicting their own preferences. Which card you actually pick is more telling than anything you would say in the abstract.