How I AIHow custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)
At a glance
WHAT IT’S REALLY ABOUT
Custom GPTs help managers scale feedback, taste, and coaching quality
- Hilary Gridley (Head of Core Product at Whoop) shares practical workflows for creating custom GPTs that act like a manager’s “rubric engine,” especially for evaluating artifacts like slide decks and writing.
- Her core method is to extract criteria from examples of “good vs. bad” work (often as simple PDFs), then iteratively refine those criteria using prompts like “Be 100 times more specific.”
- She demonstrates turning the rubric into a specialized GPT (“Deck Doctor”) that scores outputs, explains why criteria matter, and gives concrete improvement suggestions—saving managers time by handling the first 60–70% of feedback.
- Beyond decks, she shows how to use AI to sharpen thinking and writing by having it restate your thesis, surface blind spots, and restructure drafts—while keeping the final voice authentically yours. She also discusses AI adoption gaps (notably among women) and highlights playful, everyday use cases that make AI more accessible.
IDEAS WORTH REMEMBERING
5 ideasStart by defining what “good” means to you—then encode it.
Hilary’s framing is that great managers articulate “what good looks like.” Custom GPTs become useful when they are grounded in your specific standards, not generic advice.
Use good/bad pairs to let the model infer your criteria.
Collect “before and after” examples (slides, emails, docs) and have the model extract patterns. The implicit edits you make are often clearer to the AI than to you, which helps externalize your judgment.
Begin vague to explore, then get aggressively specific to converge.
She intentionally avoids overly specific initial prompts to reduce bias and discover unexpected patterns. Afterward, she tightens language with prompts like “Be 100 times more specific” to eliminate ambiguity.
Convert criteria into repeatable evaluations with a specialized GPT.
Once criteria are solid, ask the model to write the “GPT instructions” and bake in behaviors like being “ruthlessly helpful.” Add structure such as per-criterion 1–5 scores before detailed feedback.
Custom GPTs reduce prompting burden for your team.
A GPT lets teammates upload an artifact and press enter, bypassing the steep learning curve of prompting. This increases adoption by making the first experience immediately useful instead of frustrating.
WORDS WORTH SAVING
5 quotes“My favorite prompt in the world is… ‘Be 100 times more specific.’”
— Hilary Gridley
“I always start with, ‘What does good mean to me?’ And so how can I get this AI to think like me?”
— Hilary Gridley
“Criteria are what we’re trying to get to… you would already be a better manager because you’re able to communicate the criteria that you care about.”
— Hilary Gridley
“The GPT is never gonna replace you… But it can take a lot of time off your plate in terms of going from the 0 to the 60 or the 70%.”
— Hilary Gridley
“I want it to start with me, and I want it to end with me… in between is between me and the robot.”
— Hilary Gridley
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